Booty Caye

Centrally located, close to the beaches and Downtown Key West!

Location

73 Golf Club Drive
33040 Key West , FL
United States
24° 34' 32.2032" N, 81° 44' 31.2864" W
Florida US

Booty Caye

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Retirement in Key West

Reviewed by Unknown on 2026-02-23
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The rental was clean & efficient. Do not over-pack since there is not ample space (but the in condo washer & dryer were great). The 80 degree temp community pool was too notch!! Love it & will benack

home away from home

Reviewed by Unknown on 2023-11-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
loved it

Fun & Energetic 2 Bed 1.5 Bath: Booty Caye @ Key West Golf Club - RealKeyWest

Unit Code: 73GC

Booty Caye

Centrally located, close to the beaches and Downtown Key West!
Escape to your private oasis at Booty Caye, nestled within the exclusive enclave of the Key West Golf Club. This beautifully appointed 2-bedroom, 1.5-bath condominium offers a lively retreat for those seeking a longer stay amidst the lush landscapes of a golfer's paradise. With a minimum lease of 29 nights, indulge in the serenity of island time and the luxury of a thoughtfully curated home. From the moment you step in, the dynamic, colorful tiles on the staircase set the tone for a home that's as lively and vivacious as Key West itself. The terracotta tiles underfoot keep the vibe warm and inviting as they sweep through a living space that's open, airy, and eager for entertainment. The heart of the home, a fully-equipped kitchen, boasts sleek, modern appliances juxtaposed against the classic subtlety of white subway tiles. A commercial-grade refrigerator, dishwasher, and a large electric flat-top stove/oven stand ready to fuel your culinary exploits, while the adjacent dining area, with seating for four, promises intimate dinners or a spot for engaging conversation. This is complemented by additional deck seating for al fresco moments. Unwind in the living room, where a plush sofa invites you to enjoy your favorite shows on a 77-inch Smart TV, or transform it into a queen-size sleeper for visiting guests. Ascend the spirited staircase to the tranquil haven of your bedrooms, each boasting plush queen-size beds and ample storage. The front bedroom extends the invitation to the outdoors with a private balcony, an idyllic nook for solitude and reflection. For entertainment, a guest room has a projector screen, ready to turn any night into a movie night. The gated community ensures privacy and security, with the added convenience of your own parking space. * Dive into two inviting pools. * Explore a whimsical butterfly garden. * Keep active in the fitness center. Venture beyond the gates, and you're just 15 minutes from the pulsating heart of Key West—Duval Street and the Historic Downtown Seaport. Here, the spirit of the Keys is palpable in the bustling streets, brimming with local eateries, boutiques, and cultural landmarks. At Booty Caye, every detail is curated to create an unforgettable vacation experience—where luxury meets comfort, and the charm of the Keys is your daily reality. Book your month-long stay and let Booty Caye be the canvas for your Key West memories. Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. Located inside the gated Key West Golf Club community Pets considered Community Pools 15 Minutes to Duval Street/Historic Downtown Seaport
April 2026
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DatesPrice
03/01/2026 - 05/31/2026$201 /nt
03/01/2026 - 05/31/2026$220 /nt
06/01/2026 - 08/31/2026$204 /nt
06/01/2026 - 08/31/2026$248 /nt
09/01/2026 - 11/30/2026$190 /nt
09/01/2026 - 11/30/2026$304 /nt
12/01/2026 - 02/28/2027$358 /nt
12/01/2026 - 02/28/2027$485 /nt
03/01/2027 - 05/31/2027$286 /nt
03/01/2027 - 05/31/2027$414 /nt
4.5000
(2 Review)

Retirement in Key West

January 2026
, Prior Lake, MN US

Overall
4
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

The rental was clean & efficient. Do not over-pack since there is not ample space (but the in condo washer & dryer were great). The 80 degree temp community pool was too notch!! Love it & will benack

home away from home

June 2023
, Highland, IL United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

loved it

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2 Bed
1.5 Baths
Sleeps 4

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The Green Goddess

Welcome to The Green Goddess! Come stay is this gorgeous 4 bedroom, 3 bath pool home located in the gated community of the Residences at the Southernmost Point.

Location

1325 Whitehead Street
33040 Key West , FL
United States
24° 32' 47.7816" N, 81° 47' 49.4052" W
Florida US

The Green Goddess

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Jan 2026 stay

Reviewed by Kevin A. on 2026-02-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
All future winter renters need to know this house does NOT have central heat. Instead their are numerous electric space heaters that must used to warm a room which was not great. The house had some maintenance issues (electrical breakers, low coolant in AC system, etc) during our stay, but they were addressed promptly by management, so the inconvenience was minimized. We liked the location, roof top patio, and warm pool.

Green Goddess Getaway

Reviewed by Robin R. on 2025-04-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We were very pleased by the accuracy of the property description, layout, pool, upper deck, amenities and awesome customer service. Location was ideal, quiet with wonderful neighbors. Easy walk or bike ride to beaches, historic sites, restaurants, Duval St. Favs include Green Parrot, Fort Zachary, Lighthouse, Southern Most Beach and Waterfront. We enjoyed meals at Antonia's, Half Shell, Pepe's, Clemente's, Old Town Bakery and Square Grouper, just a few of the wonderful restaurants nearby. Yes, we highly recommend this property to friends and relatives. Thanks for everything, see you next year!

A property worthy of its name

Reviewed by Melanie K. on 2023-05-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
It would be difficult to improve upon any of the amenities of this beautiful home. And I'm saying that as a winter visitor of 25 years. Everything about this house is well considered. Some properties called themselves luxury accommodations, but this one truly is. Let's not forget to include Preferred Properties' exceptional management as well.

Green Goddess

Reviewed by John G. on 2023-04-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great place, great location

Green Goddess

Reviewed by John G. on 2022-03-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great place, great location and great service.

Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest

Unit Code: 1325W

The Green Goddess

Welcome to The Green Goddess! Come stay is this gorgeous 4 bedroom, 3 bath pool home located in the gated community of the Residences at the Southernmost Point.
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This secluded and peaceful property is located just off Whitehead Street, less than a block from the Southernmost Point and only a short bike ride or stroll from all of the island's top attractions. Featuring 4 bedrooms and 3 full bathrooms, this home is perfect for large groups or families. The first floor features a guest bedroom with a full shower bathroom that can be accessed from both the bedroom and the hallway, serving as the primary bathroom for the first floor. The second floor has a master bedroom with a beautiful bathroom featuring lots of mirrors and storage. The second floor also has two guest bedrooms which share a full bathroom between them. The interior of the Green Goddess is designed with mid-century modern furniture. The open-concept living area features a fully equipped kitchen with all new appliances. The living room also features a home theater with an 85-inch 4K Smart TV with cable, Apple TV, and Blue Ray/DVD player with surround sound speakers. Just outside the living room is a fun back deck and private pool. But the real highlight of this home is the romantic rooftop deck, offering a complete and unobstructed view of the sunset. Spend your evenings up there, star gazing and taking in the stunning views. Or bring a meal to the roof deck and eat on top of the world. Book your stay at the Green Goddess and experience the best Key West has to offer, including breathtaking sunset views from the romantic rooftop deck and the opportunity to view the beautiful artwork of the home's owner. Don't miss out on this unique opportunity! Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. Other items to note: There is cable TV entertainment, and the bedrooms on the second floor each have their own TV. There is WiFi throughout the house with boosters to ensure strong signals. All linens are provided for your convenience. Monthly rentals only Unfortunately, no pets are allowed. There are no bed conversions available.
April 2026
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DatesPrice
03/01/2026 - 05/31/2026$458 /nt
03/01/2026 - 05/31/2026$644 /nt
03/01/2026 - 05/31/2026$14,725 /month
06/01/2026 - 08/31/2026$406 /nt
06/01/2026 - 08/31/2026$458 /nt
09/01/2026 - 11/30/2026$356 /nt
09/01/2026 - 11/30/2026$436 /nt
09/01/2026 - 11/30/2026$13,069 /month
09/01/2026 - 11/30/2026$13,075 /month
12/01/2026 - 02/28/2027$582 /nt
12/01/2026 - 02/28/2027$741 /nt
12/01/2026 - 02/28/2027$17,603 /month
12/01/2026 - 02/28/2027$17,614 /month
03/01/2027 - 05/31/2027$689 /nt
03/01/2027 - 05/31/2027$741 /nt
4.6667
(6 Review)

Beauty of Key West!

July 2022
, Hudson, Ohio US

Overall
5

This is a beautiful home that my friends and I enjoyed staying at for the month! It was just 12 minutes from the airport, and walking distance to a ton of restaurants, bars and near by beaches. It was cozy, colorful and had all the amenities you needed for the month: a fully stocked kitchen to prep and cook all your meals, beach towels, books to read, washer and dryer, a lovely roof top to enjoy the sunrise and sunset, a lit up pool to cool off in and a grill to bbq. The house is well decorated, very modern with incredible art work all over. Each room had a different color theme that added to the uniqueness of staying at this place! It was a nice home away from home near the southernmost point of continental USA! We enjoyed our stay here and would come back again!

Jan 2026 stay

January 2026
, Mandeville, LA United States

Overall
3
Property condition
3
Location
5
Cleanliness
5
Services from rental manager
5

All future winter renters need to know this house does NOT have central heat. Instead their are numerous electric space heaters that must used to warm a room which was not great. The house had some maintenance issues (electrical breakers, low coolant in AC system, etc) during our stay, but they were addressed promptly by management, so the inconvenience was minimized. We liked the location, roof top patio, and warm pool.

Green Goddess Getaway

February 2025
, Rochester, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We were very pleased by the accuracy of the property description, layout, pool, upper deck, amenities and awesome customer service. Location was ideal, quiet with wonderful neighbors. Easy walk or bike ride to beaches, historic sites, restaurants, Duval St. Favs include Green Parrot, Fort Zachary, Lighthouse, Southern Most Beach and Waterfront. We enjoyed meals at Antonia's, Half Shell, Pepe's, Clemente's, Old Town Bakery and Square Grouper, just a few of the wonderful restaurants nearby. Yes, we highly recommend this property to friends and relatives. Thanks for everything, see you next year!

A property worthy of its name

April 2023
, Philadelphia, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It would be difficult to improve upon any of the amenities of this beautiful home. And I'm saying that as a winter visitor of 25 years. Everything about this house is well considered. Some properties called themselves luxury accommodations, but this one truly is. Let's not forget to include Preferred Properties' exceptional management as well.

Green Goddess

February 2023
, Marblehead, MA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great place, great location

Green Goddess

February 2022
, Marblehead, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great place, great location and great service.

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4 Bed
3 Baths
Sleeps 8

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Pineapple Cottage

Pineapple Cottage is a two bedroom, two bathroom home with a refreshing pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (1/2 block from Duval Street).

Location

526 Southard Street
33040 Key West , FL
United States
24° 33' 19.0188" N, 81° 48' 3.8232" W
Florida US

Pineapple Cottage

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Pineapple Cottage

Reviewed by Stacie D. on 2026-03-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We’ve stayed in this home several times. The location is close to everything you want/need and still provides a lot of privacy. Angela and Kevin at Preferred are outstanding to work with and the reason we hope to continue to rent properties from this company. Angela makes the process smooth from start to finish and Kevin is there for any of our maintenance questions. Thank you to another wonderful stay you two!

Great Vacation in Key West

Reviewed by James H. on 2026-03-04
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The Preferred Properties staff were very friendly and wonderful to work with.

Best place in key west

Reviewed by Gigi A. on 2026-01-27
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Location location location! Everything is in walking distance the cottage was beautiful and tucked away for privacy. Property management were friendly and very helpful. We are already looking to return.

A Peaceful Retreat

Reviewed by Judith L. on 2026-01-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
A lovely place with the courtyard and pool providing a relaxing environment. We ate most of our meals on the deck.

Little piece of paradise

Reviewed by Patrick B. on 2025-10-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great experience. Excellent support staff, cozy comfortable home, beautiful location steps off duval street, could not have asked for better.

Hidden Gems in paradise

Reviewed by Unknown on 2025-09-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The only thing that I found to be an issue was the musty smell thru out the house. But I guess that is to be expected due to the high heat and humidity in the area otherwise it was a very good time

Labor Day Stay

Reviewed by Jim W. on 2025-09-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a great time in your fantastic home

Better then I could imagine

Reviewed by Tom M. on 2025-06-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
What a great experience at Pineapple Cottage. We have been coming to Key West for over 25 years and this is the first time staying here. Great quiet location, very roomy, the pool is awesome and the iguana is an added bonus. We will definitely return to stay here.

Perfect!

Reviewed by Kirsten M. on 2025-06-11
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Pineapple Cottage was perfection! The private pool and back patio were amazing, beds were comfortable, home was cute and clean. Preferred Properties was excellent, they really went out of their way to make sure we were comfortable and we wanted for nothing. 10/10, we'll be back!

Amazing location yet a hidden location

Reviewed by Kimberly S. on 2025-05-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Loved our rental (Pineapple Cottage). Great location, loved the pool, tactfully decorated. comfortable

An oasis and convenient!

Reviewed by Sally S. on 2025-04-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
A wonderful oasis in the middle of Key West. Wonderful space, good communication , wonderfully appointed. Definitely would rent again!

Centrally located with the best property management on the island

Reviewed by Stacie D. on 2025-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We’re stayed at the pineapple Cottage for several years. We chose this location because of the close proximity to everything and the outdoor space. We’ve rented from other companies, but Angela at Preferred Properties is by far the most professional and knowledgeable we’ve worked with. The house is always clean and ready on time. We can’t wait to come back next year!

Our Oasis

Reviewed by Beverly C. on 2025-02-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The location of Pineapple Cottage couldn't be better, close to all the action but you'd never know it. The pool was wonderful. We chose to have it heated and it was prefect for floating after getting in from the beach. The cottage itself was exactly as described. Angela from Preferred Properties was the there to answer all of our questions from check-in to check out. We will be returning!

CENCI

Reviewed by nick c. on 2025-01-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
It was a clean and wonderful atmosphere
Can't wait to come back

Wonderful Stay!

Reviewed by Jacob E. on 2024-12-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Excellent in every way! No complaints whatsoever.

Pineapple House 2024

Reviewed by Kevin F. on 2024-12-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Everything went perfect from the rental agency support and communication, house cleanliness and comfort, pool and location. We are already booked for next year!

Great location and excellent home

Reviewed by Erik K. on 2024-12-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This place is awesome. Nice pool and tropical garden. Very private. House had everything we needed and more. Super clean and communication with the host was quick and simple.

Perfect for Two Couples!

Reviewed by William T. on 2024-11-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful time at this oasis. Off of Duval St so you are in your own little world. Quiet and comfortable it is perfect for two couples. Upstairs has a great main suite with a big sitting room. Clean and ready for your use. Property management company is wonderful with communication. Property very well maintained. Great location. You can walk everywhere from here. Coffee shop right next door, plenty of foodie spots in every direction.

Excellent Stay

Reviewed by Peter S. on 2024-10-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The Pineapple Cottage is a great place to stay if you are heading to key west. Location is prime with loads of space for outdoor relaxation. Quiet at night even though the location is in the heart of town. Management company was great with communication and made our stay a breeze.

Third times a charm

Reviewed by Mason L. on 2024-10-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was our third visit to Pineapple Cottage, we love this place and will continue to come back. The location can not be beat, everything walking distance. Thank again Preferred Properties for another great stay.

An oasis in downtown key west

Reviewed by Carole G. on 2024-08-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had the most perfect stay at pineapple cottage. It was absolutely brilliant- the pool was perfect, the house was immaculate but above all the location was incredible. It was just a 2 minute walk from Duval Street and all the exciting bars and shops, but once in the property all the hustle disappeared and it was serene. Highly recommend
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Carole, Thank you so much for your lovely review! We're thrilled that you had a perfect stay at Pineapple Cottage and enjoyed the pool, cleanliness, and unbeatable location. It's wonderful to hear that the cottage offered both the excitement of Duval Street and the serenity you were looking for. We would love to welcome you back anytime. Thanks again for highly recommending us!

Excellent. Oasis hidden near Duval

Reviewed by Jack B. on 2024-07-28
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Stayed with Family of Five during July.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Jack, Thank you for the fantastic review! We're so glad that you and your family of five had an excellent stay at Pineapple Cottage in July. It's great to hear that the cottage was a perfect oasis for your family getaway. We look forward to welcoming you back for another stay!

Great place with privacy.

Reviewed by Phillip R. on 2024-07-11
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Had a great time in Key West while staying at the pineapple cottage. The home was clean are ready early. Management kept us I formed throughout the booking process and leading up to our arrival. AC worked great and private pool was the main event. Spent evenings cooling off after a day waking around town or relaxing on the beach. Thank you.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Phillip, We appreciate your thoughtful review! It’s fantastic to hear that you had a great time in Key West and enjoyed the privacy, cleanliness, and especially the pool. We’re also glad the AC kept you cool and comfortable during your stay. We’d be delighted to host you again on your next trip.

Wonderful Place

Reviewed by Gary . on 2024-06-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great location. Lots of privacy and quiet time when you need it. Will be back..
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Gary, Thanks for the wonderful review! We’re thrilled that you enjoyed the location and found the privacy and quiet exactly what you needed. We look forward to your return for more relaxation in Key West!

Amazing

Reviewed by Phillip T. on 2024-06-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Amazing!
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Phillip, Thank you for the kind review! We’re so happy that your stay was nothing short of amazing. We hope to have you back at Pineapple Cottage again soon!

Another great trip....

Reviewed by Mason L. on 2024-04-28
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is our second time staying at Pineapple Cottage. We absolutely love this rental. It is in the heart of everything, yet so private at the same time. Everything you need is here. We will be back.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Mason, Thank you for your fantastic review and for choosing Pineapple Cottage for a second time! It’s great to hear that you love the rental and the perfect balance of being in the heart of everything while maintaining privacy. We’d be happy to host you again for your third stay!

5 Days in Key West

Reviewed by David M. on 2024-04-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Pineapple Cottage is perfectly located just a half block from Duval. The cottage was exceptionally clean. Only negative was the beds, new mattresses would make the cottage perfect. Out door area was also very nice, with a grill and plenty of seating. We would definitely recommend this cottage to friends and family.
Manager response on 2024-04-19 - Response from Preferred Properties Management LLC
Thank you for the wonderful review. I am happy to say that new mattresses have been ordered and have been replaced on April 16, 2024.

Pineapple Cottage

Reviewed by Michele C. on 2024-04-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a wonderful time at Pineapple cottage.
Great location, great pool, comfortable home and easy to reach property manager. Thank you.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Michele, Thank you for the wonderful review! We’re thrilled that you enjoyed your stay, especially the location, pool, and comfort of the home. It’s great to know our team was helpful and responsive. We hope to welcome you back in the future!

Key West Rental

Reviewed by Jill Q. on 2024-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The location of the cottage is perfect, close to everything but a bit away from the noise. The pool and yard is an adorable oasis. For the nightly price it would be reasonable to expect nicer beds, paint touch ups, repair of cracked stairs, repaired decking, replacement of torn patio furniture, etc.
Manager response on 2024-03-21 - Response from Preferred Properties Management LLC
Thank you so much for sharing your feedback regarding the house. We truly appreciate your insights. Just to update you, we have a brand new mattress for the upstairs area on order, and our new lawn furniture is also scheduled for delivery very soon. Living in Key West poses a unique challenge as we don't have local stores readily available, which means most items have to be ordered in advance. As our property serves as a transient home, we have to balance small repair projects around our guests' stays. Rest assured, we will address these repairs as soon as time allows. Once again, thank you for choosing to stay with us. Your feedback helps us improve and provide a better experience for our guests. We look forward to welcoming you again in the future.

Another wonderful stay at Pineapple Cottage, Key West

Reviewed by Gerold T. on 2024-03-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Staying at the Pineapple Cottage allows you to have an effortless enjoyable vacation in Key West! It's central location allows you to walk wherever you want to go. No need to rent any type of transportation. The private pool retreat allows you to just relax when you choose to. This is our 3rd stay and we will be back for our 4th!
Manager response on 2024-03-21 - Response from Preferred Properties Management LLC
Thank you, our repeat guests are truly appreciated.

A wonderful tranquil week in Key West

Reviewed by Unknown on 2024-02-12
Recommend to Others
Property condition
Location
Cleanliness
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Preferred Properties was the best management company I have ever worked with in Key West. Thank you so much for the great communication, kind and friendly service.
The downstairs bed had seen better days, but okay for one person. otherwise the property was absolutely beautiful, quiet and so private. All the comforts of home were provided.
Manager response on 2024-02-13 - Response from Preferred Properties Management LLC
Thank you for the nice comments and will work on replacing the guest mattress. All suggestions and comments are truly appreciated! Hope to have you back in the near future.

Birthday Surprise

Reviewed by Larry R. on 2023-12-29
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If we ever go back to Key West, we are absolutely going to stay here. The house is private and in a perfect location. Thank you!

Great location!

Reviewed by Yelena L. on 2023-11-30
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We enjoyed our stay so much! It is close to the busy Duval street, but at the same time feels very private. Great experience overall, although I would have proffered a heads up about a pool guy showing up and just walking though in the middle of the day - was very much unexpected :)

Adorable cottage

Reviewed by Melinda S. on 2023-11-28
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This cottage is just adorable! Very spacious with bedrooms up and down. We loved the outdoor patio as we had coffee every morning out there. We would relax in the pool in the afternoon. Everything was within walking distance.

review

Reviewed by Jim W. on 2023-09-28
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good

Great location

Reviewed by Charles H. on 2023-08-03
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This place is amazing. You can’t beat the location, walk to everything in minutes. The house and pool area were great. Definitely will be my go to place to rent.

Hidden Gem

Reviewed by Jason C. on 2023-07-30
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Perfect location. Management was great. Pool was relaxing.

Great house & location!

Reviewed by Unknown on 2023-05-28
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Awesome!

Great house, and location!

Reviewed by Stacie D. on 2020-04-01
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We've been coming to Key West for the last 8 seasons. We normally rent from a different company, but they didn't have a home that would work. We couldn't have been happier with Preferred Properties, and Angela specifically. She was great to work with, and the house was one of the best we've stayed in. The location is awesome, and the pool was extremely private, which is what we wanted. We will for sure try to stay here again, if it's available on our next trip.

Best Thanksgiving Ever

Reviewed by Unknown on 2019-12-19
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every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything

A Great Place to Stay!

Reviewed by April G. on 2019-12-18
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We enjoyed our stay at Pineapple Cottage! It was very neat and clean, exactly as the pictures show. We loved the pool and the fact that you could request to heat it. The cottage is close to shopping and restaurants. In a walks distance to everything we wanted to see. Excellent customer service from the property management. We felt very comfortable and valued as guests. We would love to stay here again in the future.

Outstanding rental experience

Reviewed by Darcie C. on 2020-01-20
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This rental experience was top-notch from the initial booking to the final departure. Staff was helpful and communication was excellent. Property was immaculate, and exactly as described in the summary. Best experience I've had renting a vacation property - I plan to return to the area every year, and wouldn't dream of using any other agency to help plan my stay.

Key West - Pineapple Cottage

Reviewed by Edward D. on 2021-01-28
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This was a reschedule due to early 2020 COVID restrictions. The team at PPM assisted us in finding a new date and accomodating our new needs. The property was properly prepared and was well-equipped. This lead to a very enjoyable stay.

Amazing Property and Location!!!!

Reviewed by Garrett B. on 2020-01-14
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The property was exactly what we had hoped for and the location was even better than expected. We really enjoyed the pool and the proximity to Duval. The parking spot was an added bonus!

Long overdue!

Reviewed by Samantha H. on 2021-05-10
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Our group waited an extra year to visit Key West and we were not disappointed in our choice to stay at the Pineapple Cottage. The house was immaculate! The floor plan was ideal for traveling with another couple as it made it feel like two separate spaces. Every necessary utensil was provided in the kitchen. The pool and outdoor space were amazing and relaxing. We were just steps from Duval but in our own little oasis. We will definitely return!

Perfect oasis in old town

Reviewed by Rod S. on 2021-04-15
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This was our second time renting the Pineapple Cottage and once again it was perfect. The location, the pool, the quiet seclusion, and the cleanliness are excellent. If we come back to KW, we will definitely rent this cottage!

Pineapple Cottage

Reviewed by Robert W. on 2021-05-04
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Location, Location, Great place , clean , Can't wait to return next year

2nd Stay in Paradise at Pineapple Cottage!

Reviewed by Gerold T. on 2021-03-15
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Our 2nd stay at Pineapple Cottage was better than our 1st visit back in 2017. The centralized location in Old Town is perfect! No need to rent a vehicle since everything is within a mile! The home and the private pool is truly a wonderful piece of paradise! Can't wait for our 3rd visit!!!

Our Thanksgiving Tradition

Reviewed by Unknown on 2020-12-23
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We had such a great Thanksgiving in 2019 at Pineapple Cottage we said we’d be back and we made it happen! The house was perfect for our family. Quiet, private and a beautiful backyard and pool. Here’s to our new tradition. We’ll be back in 2021!

Fabulous !

Reviewed by Unknown on 2020-06-11
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Wonderful property, great location, and superior customer service from Preferred Properties
Manager response on 2020-07-09 - Response from Preferred Properties Management LLC
Thank you John for your nice review. We appreciate our guests and always try to make sure they have a nice time!

Gem in the Heart of it All

Reviewed by Roger A. on 2020-07-07
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We spent the first half of our vacation at the Pier House and actually preferred this property with its private pool, iguanas, beautiful floral landscape, dedicated parking space, well-appointed kitchen and great location to all in midtown Duval.
Manager response on 2020-07-09 - Response from Preferred Properties Management LLC
Thank you, Roger! The Pier House is a fantastic property, thankfully you were able to also experience Pineapple Cottage and now know why so many people choose to stay in a vacation rental when visiting Key West. We hope you visit us again someday!

The best place to stay in Key West!

Reviewed by Sammy S. on 2020-11-26
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My husband and I have stayed at Pineapple Cottage many times. We love the privacy, the pool and we simply feel very comfortable in the cottage! We loved the upgrades! Preferred Properties have always been very good to us, they are indeed number one when it comes to vacation rentals!
Manager response on 2020-12-02 - Response from Preferred Properties Management LLC
Sammy, Thank you for your review and also thank you for your contributions to our community. Congrats on the Smart Ride! Very impressive. We look forward to your visit each year. You always help make our product even better with your perfect suggestions and your pleasant hints when we forgot the coffee maker after the upgrades. We are glad we were able to find one quickly for you because Cuban Coffee Queen every day, while amazing, may not be the best option for relaxing and recharging. We really appreciate your repeated business and it is becoming ever more wonderful getting to know you guys more. Great music was overheard anytime we were near the property! :-)

JUST WHAT WE NEEDED ❤️

Reviewed by JAMES T. on 2020-08-18
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I cannot say enough great things about the staff at Pineapple...they are all amazing!! The house, the pool, and the location was perfect in every way! We rented a vehicle and only used it once to drive to Marathon to look at some properties. If you have no plans to drive anywhere save the money on the rental....the location is within walking distance to everything! We will be back very soon!!

Great Stay in Pineapple Cottage

Reviewed by Unknown on 2021-05-04
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We had a great time in Key West (this was our first time). The Pineapple Cottage was great! The pool was a savior. We were in it every day prior to going out and hitting the town mid-afternoon. Made several iguana friends each day in the backyard...

The Best Cottage in Key West!

Reviewed by Mandy D. on 2021-06-01
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The Pineapple Cottage was absolutely perfect!! It was centrally located, fully stocked, clean, spacious and the pool was an oasis. The owner was extremely accommodating and checked in frequently. We had the best time and we will be back! Thanks!!

Fabulous

Reviewed by Trish K. on 2022-01-18
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Location...fabulous. Grocery store one block
Outdoor space...fabulous......grill...fabulous
Pool...fabulous
Kitchen ...fabulous....everything you could possibly need
Best place in Key West.....we stayed other places but none compare
No need to look further this place has it all...fabulous
Great customer service...Angela was also fabulous

Pineapple Cottage Rental

Reviewed by Kevin F. on 2021-12-13
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The property was very nice and well maintained. The area is also quiet and in a great location.

Key West vacation

Reviewed by Don A. on 2021-03-22
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We had a great time and were extremely impressed by the Pineapple Cottage. On any future visits to Key West, we would only consider staying there again!

Lovely cottage in great location

Reviewed by Sandy M. on 2021-04-22
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The home was exactly as advertised. Well appointed and comfortable. The location is perfect - steps away from Duval but hidden away and very private. We will definitely return!

Florida Keys Getaway

Reviewed by Karen H. on 2021-06-07
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We took a 41st wedding anniversary trip with another couple who were celebrating their 50th birthdays. We spent a week in the Keys with our last 3 days at Pineapple Cottage. We definitely saved the best for last, although each of our 3 VRBO properties were wonderful in their own unique way. The location of Pineapple Cottage was awesome! Right in the middle of everything, yet it felt like a private hidden oasis! Well equipped and very comfortable property with its own pool!

Perfect

Reviewed by Norm M. on 2021-04-10
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House location could not have been better. The home had everything that you would need. Pool was clean and quite. Privacy was not an issue. I would rent this home again without a 2nd thought.

Pineapple Cottage is Fantastic!

Reviewed by Gregory E. on 2021-06-24
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We loved our stay at the Pineapple Cottage in Key West! We are a family of two adults and two daughters 18 & 25 years old. The entire experience from the booking, arrival, the stay, and departure was handled in the best possible way by Preferred Properties on behalf of the owners. Such great communication and accessibility (even after hours). The location of the property is ideal; 1/2 block from Duval Street but completely secluded and private with a large (by Key West standards) private swimming pool surrounded by decks. You don't even know you are that close to the craziness of Duval Street when you are sitting by the pool in the back yard. There are breakfast places, coffee houses, restaurants, a small grocery store, and a liquor store all within 2 blocks of the property. The house itself is perfectly laid out and contained absolutely everything we needed during our 1 week stay. The property owners thought of everything! We rented bikes for the week to see the island and Preferred Properties even arranged that for us prior our visit. The property was clean when we arrived and is in good condition considering the amount of rentals they must have at this property all year long. I honestly can't come up with a complaint or downside to staying at this wonderful property. I will recommend that you bring bug spray because it was very buggy (mosquitos and gnats) at the property; however, that is probably just a function of the weather in Key West in June most likely. If there is ever any availability here in the near future, we will definitely come back to the Pineapple Cottage. Once you stay here, it will be your "go to" for lodging in Key West.

Relax

Reviewed by Larry P. on 2021-11-12
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Great place to relax and enjoy all Key West has to offer. Location is perfect within a short walk to either end of Duval. We have stayed there many times and its always perfect. The pool and deck area seems like there is nothing around.

A hidden gem in a perfect location

Reviewed by Krista I. on 2021-07-01
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We stayed here for five nights in late June. The house was very clean and the pool was amazing. It was a short walk to everything so we didn’t even rent bikes or a golf cart. We had a wonderful time here and hope to visit again in the future.

Awesome house

Reviewed by Nicki C. on 2021-08-09
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This house was perfect! We went in August so it was super hot outside..... the pool was a godsend.
The house was neat and had everything we needed.
I am going to miss waking up and walking a few doors down to get my Cuban con leche coffee������
We all loved are daily iguana visits!!!

Absolutely magical property!

Reviewed by Robert O. on 2021-07-16
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We had a fantastic stay in this little oasis in the heart of Key West. The pool and landscaping were amazing and provided ample privacy and relaxation. The staff at Preferred Properties were top notch and attentive. Of all the vacation properties we have stayed at, this was by far the cleanest and most well-cared for property we have experienced. We will be back!

Pineapple Cottage

Reviewed by Stacie D. on 2022-03-30
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This is one of our favorite houses to stay in. The location is fantastic, walkable to everything, 1/2 block from Duval, but very private. Highly recommend. The team at Preferred Properties is top notch.

This is the spot!!

Reviewed by David S. on 2021-12-17
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Everything you need!! Location is perfect 1/2 block off Duval yet no noise. Block from coffee and store, both convenient. Nothing negative about this property. Already planning next year!!

Great Stay

Reviewed by Unknown on 2021-07-06
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Loved everything about the house. It was very comfortable and exactly as described. Very conveniently located and the pool was the perfect escape from the heat. We would definitely stay here again if we are in Key West.

Pineapple Perfection

Reviewed by Richard K. on 2022-05-22
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Great property ,Great location ,Awesome management team, we will definitely be back !

Key West Getaway

Reviewed by Unknown on 2021-12-06
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Our experience was such an smooth one from renting, arriving, our stay and our departure. The place is amazing! The location was just perfect. We were able to keep our vehicle parked off the street (which is a big thing considering the public parking situation). We walked just about anywhere we needed to go which was a blessing. We could walk to sunset each day!
For four adults, the accommodations were awesome and exactly what we hoped for. The pictures and the property matched well. Beds were comfortable, all appliances were in good working order, a/c was good and the full size washer and dryer was a great bonus!
We would rent this property again if it is available when we return to Key West. The management company is very professional and keeps you up to date as you get near to your stay.

Pineapple Cottage

Reviewed by Robert W. on 2022-05-09
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As always Great stay at The Pineapple Cottage. Great location , clean. Can't wait for next year!!

Pineapple Cottage

Reviewed by Unknown on 2021-07-07
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Pineapple Cottage is perfect for a stay in Key West! So conveniently located but with loads of privacy and equipped with everything you need.

Peace and Quiet in the middle of it all

Reviewed by Unknown on 2022-02-08
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We had a lovely vacation at Pineapple Cottage. Everything lived up to the pictures and descriptions - which does not always occur. We loved the location, close to everything we wanted to do, yet quiet and private. The pool and deck were perfect for late afternoon relaxation. The only negative was the parking spot (which isn't always available at other properties). The bad thing was, it was next to trees, and evidently the local birds did not approve of our car, and showed their feelings by decorating it with their droppings. (Not sure how to fix that, but it was a negative...) We'd return in a heartbeat for our next visit to Key West!

Great Oasis

Reviewed by Michael H. on 2021-11-23
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We really enjoyed the Pineapple Cottage. It is located for easy access to bars, grocery, restaurants, and other attractions. We loved it!!

Pineapple cottage was excellent!

Reviewed by Kelly M. on 2021-09-11
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Pineapple cottage is a great place to stay in Key West. It is totally private, Very clean and well appointed and in a great location! Preferred Properties Staff were very helpful and accommodating.

Very Relaxing

Reviewed by Lawrence M. on 2021-12-29
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Most enjoyable. Great location, Nothing like a Key West Christmas!

Short getaway

Reviewed by Unknown on 2021-09-11
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Overall we were happy with Pineapple Cottage. The interior was perfect for 2 couples and in good condition. The location was great. The exterior was nice but could use some tlc and the furniture needs to be replaced. It rained and the chairs stayed wet for 2 days. They were unusable as they have some sort of padding in them that did not dry. One of the chaise lounges was coming apart and a bit unsightly. The fountain was nice but covered with mold. Plants were pretty but trees growing into the awning seemed a bit strange. One thing to know, this property is behind a store and not visible from the road.

Our spring get away

Reviewed by Unknown on 2022-04-26
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We had a wonderful experience staying at Pineapple Cottage. As nice as the interior was, the outside living space was magnificent. Except for sleeping inside, we were outside enjoying the pool. Definitely a place we would stay again and suggest to other people.

The BEST Vacation...round 2!

Reviewed by Krista I. on 2022-08-11
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My husband and I along with my sister and her husband stayed at the cottage for a second time this summer and it was everything we hoped for! The property was very clean and very private. We loved hanging out in the pool and the location to Duval street can't be beat! The Preferred Properties team was also so helpful. kind and accommodating to our needs. We will definitely be back again!

Paradise in the Middle of Paradise

Reviewed by Elizabeth J. on 2022-07-03
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Pineapple Cottage is a hidden gem. From the cozy comfortable cottage to the beautiful lush pool area. This is a great place to relax!

Amazing cottage hide away

Reviewed by Travis B. on 2022-07-02
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I dont know how many houses like this are hid away in Key West, but we are very fortunate to have found the Pineapple Cottage. Located so close to everything. Go walking along Duval, get a little sweaty, just come right back and jump in the pool! With your very own parking spot, located right behind the house, we never had to worry.

Best little hideaway in Key West

Reviewed by Christine E. on 2022-10-11
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Adorable cottage centrally located. very spacious. the outdoor area was spectacular, the concierge service was incredible. can’t wait to come back.

The best in key west

Reviewed by Trish K. on 2023-01-18
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Pineapple cottage is amazing in every way.....clean, well appointed kitchen, great outdoor space and great location. The grocery store just a block away. close to duval for all the restaurants and bars but far enough away to have peace and guiet. We’ve stayed her 2 years in a row and hope to be back next year....love it !

Wish I could give 10 stars!!!

Reviewed by Kelli S. on 2022-10-24
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This place was amazing from location to bedding to NO noise and ALL the privacy a person and family could need!. Everything was amazing! The staff at the office welcomed us when we were there early and Kevin was able to get us what we needed. Angela was a HUGE help as well- even keeping us posted after the Hurricane came through before we came down. Clean, TONS of space and convenient. Will definitely be coming back!!!!!

Hidden Retreat

Reviewed by Michelle B. on 2022-08-19
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We absolutely LOVED our time at this property. The location was perfect. Everything about the property was exceptional. The outdoor space was a relaxing retreat. Indoor space was clean, updated and had everything we needed for our stay. We can’t wait to come back and have already recommended this property to friends. Thank you for making our time in Key West special!

Pineapple Cottage

Reviewed by Mark M. on 2022-11-20
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Everything about this property was great. The location was perfect. The backyard is very secluded and the pool was wonderful for relaxing after a few hours of action on Duval street. The pool was clean and warm and totally private. The Preferred Properties office is very close and the people there were very helpful and professional. We will definitely stay here again.

Love the Pineapple Cottaage!

Reviewed by Michael B. on 2023-03-24
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Pineapple Cottage is a great place! So close to Duval St. but you wouldn’t know it from the house. Love the pool and the grounds. We’ve stayed there 3 years in a row and would stay there again and again.

Lovely home, friendly helpful staff.

Reviewed by Melody M. on 2022-11-02
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Great location, close to everything! The staff at the rental agency was very communicative and helpful. The house was perfect for two couples and room for more. We enjoyed the pool too.

Best location

Reviewed by Stacie D. on 2023-03-19
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We’ve stayed at this home several times. The location is great with several restaurants and shops in close walking distance. The layout is perfect for two couples. The outdoor space is exactly what we were looking for with a large pool and plenty of deck/seating space. Preferred Properties and Angela specifically are easy to work with and very responsive. We look forward to booking this place again.

BEST LOCATION!!!

Reviewed by Leigh P. on 2022-07-31
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This Key West house was even better in person! So clean, so private, and best location to everything!!!! Will absolutely stay here again in the future.

Don’t stay here

Reviewed by gene c. on 2022-06-25
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Seriously I am concerned if I say just how much my girls and I enjoyed our stay the price will go up and availability will go down! Just a spectacular home in a perfect location! Old town Key West is so much fun for everyone! We can’t wait to return and hopefully stay at pineapple cottage...

Florida Keys getaway

Reviewed by Denise H. on 2022-11-27
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Pineapple Cottage was a great location just off Duval. Enjoyed the pool in the evenings. Management was great. Highly recommend!

Perfect Family Vacation

Reviewed by Unknown on 2023-04-10
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Great Property! Had everything you could possibly need. Enjoyed Family time in the pool and the location was perfect!

Location Location Location

Reviewed by Andrea Y. on 2023-02-08
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Great place and so easily accessible to everything. Definitely enjoyed the heated pool!

Pineapple Cottage

Reviewed by Unknown on 2023-05-06
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Great location Clean and well appointed. Enjoyed our stay. Group of 4, easily accommodated.

Pineapple Cottage Love It! Didn’t want to leave it!

Reviewed by Unknown on 2022-12-28
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Pineapple Cottage has everything needed for a great getaway close to the Old Town hotspots yet quiet enough to relax by the pool and chill. We will definitely seek to stay again. Working the the staff from Preferred Properties was easy, open and concise communication!

Always LOVE Pineapple Cottage

Reviewed by Jaime M. on 2023-04-06
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Always LOVE staying at Pineapple Cottage. The place itself is awesome, and you can’t beat the location. The staff, especially this most recent time, was beyond friendly; really great.

Private paradise

Reviewed by Tom K. on 2023-04-25
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Great location, perfect layout for two couples, very private pool

Secluded paradise

Reviewed by Unknown on 2023-01-29
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Very private oasis in a busy town. Nicely appointed, clean VRBO with beautiful patio space and awesome heated pool. Great location for popular tourist destinations. Has it's own dedicated off-street parking space. Excellent communication with Preferred properties folks. Would highly recommend.

Media

PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval

Unit Code: 526S

Pineapple Cottage

Pineapple Cottage is a two bedroom, two bathroom home with a refreshing pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (1/2 block from Duval Street).
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation. As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring your privacy and creating a serene atmosphere. Inside, the cottage features an open living area and kitchen space, perfect for easy flow and entertaining. The living area is equipped with a fully loaded entertainment system, including cable TV, a sound system, CD player, and DVD player. You'll also find board games for some indoor fun, whether in the living room or at the outdoor table. The kitchen is fully equipped and includes a breakfast bar with bar chairs, providing a convenient division from the couch and comfortable viewing chairs in the living room. On the first level of the cottage, there is a full bathroom and a hidden bedroom tucked away to the right of the kitchen. This bedroom features a queen-size bed and all the amenities necessary to ensure a comfortable stay. You can choose to keep the curtains and blinds closed for a peaceful sleep-in or open them up to let the tropical sun awaken you for an adventurous day. The second floor of the cottage offers another spacious living area with cable TV, a large comfortable sofa, and chairs for relaxation. The master bedroom on this level boasts a king-size bed and an en-suite full bathroom. Additionally, the washer and dryer are conveniently located in this bathroom for the guests' use. The backyard of the Pineapple Cottage is a true haven. With its sparkling pool, grill, and dining areas, you have everything you need to enjoy meals at home while entertaining and making the most of your vacation. The cottage location in the Old Town district allows you to easily walk to Duval Street, where you'll find a variety of shopping, beaches, and restaurants in close proximity. Overall, Pineapple Cottage offers top-of-the-line amenities and comfort, ensuring a delightful and enjoyable stay in Key West. Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. **Pool heat is optional at $25 a day.**
April 2026
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Age 24 and under.
DatesPrice
04/05/2026 - 04/09/2026$730 /nt
04/05/2026 - 04/09/2026$960 /nt
04/12/2026 - 04/16/2026$730 /nt
04/12/2026 - 04/16/2026$960 /nt
04/19/2026 - 04/23/2026$730 /nt
04/19/2026 - 04/23/2026$960 /nt
04/26/2026 - 04/30/2026$730 /nt
04/26/2026 - 04/30/2026$960 /nt
05/03/2026 - 05/07/2026$730 /nt
05/03/2026 - 05/07/2026$960 /nt
05/10/2026 - 05/14/2026$730 /nt
05/10/2026 - 05/14/2026$960 /nt
05/17/2026 - 05/21/2026$730 /nt
05/17/2026 - 05/21/2026$960 /nt
05/24/2026 - 05/28/2026$730 /nt
05/24/2026 - 05/28/2026$960 /nt
05/31/2026 - 05/31/2026$960 /nt
05/31/2026 - 05/31/2026$730 /nt
03/01/2026 - 05/31/2026$730 /nt
03/01/2026 - 05/31/2026$1,130 /nt
03/01/2026 - 05/31/2026$5,408 /wk
03/01/2026 - 05/31/2026$7,084 /wk
03/01/2026 - 05/31/2026$24,546 /month
03/01/2026 - 05/31/2026$26,181 /month
06/01/2026 - 08/31/2026$572 /nt
06/01/2026 - 08/31/2026$1,045 /nt
06/01/2026 - 08/31/2026$4,190 /wk
06/01/2026 - 08/31/2026$7,938 /wk
06/01/2026 - 08/31/2026$21,406 /month
06/01/2026 - 08/31/2026$27,812 /month
09/01/2026 - 11/30/2026$452 /nt
09/01/2026 - 11/30/2026$1,268 /nt
09/01/2026 - 11/30/2026$3,708 /wk
09/01/2026 - 11/30/2026$10,334 /wk
09/01/2026 - 11/30/2026$16,566 /month
09/01/2026 - 11/30/2026$34,855 /month
12/01/2026 - 02/28/2027$6,571 /wk
12/01/2026 - 02/28/2027$17,549 /wk
12/01/2026 - 02/28/2027$40,688 /month
12/01/2026 - 02/28/2027$52,949 /month
03/01/2027 - 05/31/2027$7,483 /wk
03/01/2027 - 05/31/2027$12,838 /wk
03/01/2027 - 05/31/2027$32,097 /month
03/01/2027 - 05/31/2027$48,953 /month
4.9860
(143 Review)

Pineapple Cottage

March 2026
, Ypsilanti, MI United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We’ve stayed in this home several times. The location is close to everything you want/need and still provides a lot of privacy. Angela and Kevin at Preferred are outstanding to work with and the reason we hope to continue to rent properties from this company. Angela makes the process smooth from start to finish and Kevin is there for any of our maintenance questions. Thank you to another wonderful stay you two!

Great Vacation in Key West

February 2026
, Henrico, VA United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

The Preferred Properties staff were very friendly and wonderful to work with.

Best place in key west

January 2026
, Sewell, NJ US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

Location location location! Everything is in walking distance the cottage was beautiful and tucked away for privacy. Property management were friendly and very helpful. We are already looking to return.

A Peaceful Retreat

December 2025
, Lake Worth Beach, FL United States

Overall
5
Property condition
4
Location
5
Cleanliness
5
Services from rental manager
5

A lovely place with the courtyard and pool providing a relaxing environment. We ate most of our meals on the deck.

Little piece of paradise

October 2025
, Crest Hill, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great experience. Excellent support staff, cozy comfortable home, beautiful location steps off duval street, could not have asked for better.

Hidden Gems in paradise

September 2025
, York, PA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The only thing that I found to be an issue was the musty smell thru out the house. But I guess that is to be expected due to the high heat and humidity in the area otherwise it was a very good time

Labor Day Stay

August 2025
, Beavercreek, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time in your fantastic home

Better then I could imagine

June 2025
, Sidney, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

What a great experience at Pineapple Cottage. We have been coming to Key West for over 25 years and this is the first time staying here. Great quiet location, very roomy, the pool is awesome and the iguana is an added bonus. We will definitely return to stay here.

Perfect!

June 2025
, Greensboro, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage was perfection! The private pool and back patio were amazing, beds were comfortable, home was cute and clean. Preferred Properties was excellent, they really went out of their way to make sure we were comfortable and we wanted for nothing. 10/10, we'll be back!

Amazing location yet a hidden location

May 2025
, Shepherdsville, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved our rental (Pineapple Cottage). Great location, loved the pool, tactfully decorated. comfortable

An oasis and convenient!

March 2025
, Cropwell, AL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A wonderful oasis in the middle of Key West. Wonderful space, good communication , wonderfully appointed. Definitely would rent again!

Centrally located with the best property management on the island

March 2025
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We’re stayed at the pineapple Cottage for several years. We chose this location because of the close proximity to everything and the outdoor space. We’ve rented from other companies, but Angela at Preferred Properties is by far the most professional and knowledgeable we’ve worked with. The house is always clean and ready on time. We can’t wait to come back next year!

Centrally located with the best property management on the island

March 2025
, Ypsilanti, MI United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We’re stayed at the pineapple Cottage for several years. We chose this location because of the close proximity to everything and the outdoor space. We’ve rented from other companies, but Angela at Preferred Properties is by far the most professional and knowledgeable we’ve worked with. The house is always clean and ready on time. We can’t wait to come back next year!

Our Oasis

February 2025
, Hammonton, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The location of Pineapple Cottage couldn't be better, close to all the action but you'd never know it. The pool was wonderful. We chose to have it heated and it was prefect for floating after getting in from the beach. The cottage itself was exactly as described. Angela from Preferred Properties was the there to answer all of our questions from check-in to check out. We will be returning!

CENCI

December 2024
, RONKONKOMA, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It was a clean and wonderful atmosphere
Can't wait to come back

Wonderful Stay!

December 2024
, Wellston, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Excellent in every way! No complaints whatsoever.

Pineapple House 2024

December 2024
, Plainfield, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Everything went perfect from the rental agency support and communication, house cleanliness and comfort, pool and location. We are already booked for next year!

Great location and excellent home

December 2024
, Finksburg, MD US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This place is awesome. Nice pool and tropical garden. Very private. House had everything we needed and more. Super clean and communication with the host was quick and simple.

Perfect for Two Couples!

October 2024
, Leawood, KS United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a wonderful time at this oasis. Off of Duval St so you are in your own little world. Quiet and comfortable it is perfect for two couples. Upstairs has a great main suite with a big sitting room. Clean and ready for your use. Property management company is wonderful with communication. Property very well maintained. Great location. You can walk everywhere from here. Coffee shop right next door, plenty of foodie spots in every direction.

Excellent Stay

October 2024
, Commerce City, CO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The Pineapple Cottage is a great place to stay if you are heading to key west. Location is prime with loads of space for outdoor relaxation. Quiet at night even though the location is in the heart of town. Management company was great with communication and made our stay a breeze.

Excellent Stay

October 2024
, Commerce City, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The Pineapple Cottage is a great place to stay if you are heading to key west. Location is prime with loads of space for outdoor relaxation. Quiet at night even though the location is in the heart of town. Management company was great with communication and made our stay a breeze.

Third times a charm

September 2024
, Bartlett, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was our third visit to Pineapple Cottage, we love this place and will continue to come back. The location can not be beat, everything walking distance. Thank again Preferred Properties for another great stay.

An oasis in downtown key west

August 2024
, Hinckley, Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had the most perfect stay at pineapple cottage. It was absolutely brilliant- the pool was perfect, the house was immaculate but above all the location was incredible. It was just a 2 minute walk from Duval Street and all the exciting bars and shops, but once in the property all the hustle disappeared and it was serene. Highly recommend

Manager's Response

Hi Carole,

Thank you so much for your lovely review! We're thrilled that you had a perfect stay at Pineapple Cottage and enjoyed the pool, cleanliness, and unbeatable location. It's wonderful to hear that the cottage offered both the excitement of Duval Street and the serenity you were looking for. We would love to welcome you back anytime. Thanks again for highly recommending us!

Excellent. Oasis hidden near Duval

July 2024
, Davidson, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Stayed with Family of Five during July.

Manager's Response

Hi Jack,

Thank you for the fantastic review! We're so glad that you and your family of five had an excellent stay at Pineapple Cottage in July. It's great to hear that the cottage was a perfect oasis for your family getaway. We look forward to welcoming you back for another stay!

Great place with privacy.

June 2024
, Princeton, LA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Had a great time in Key West while staying at the pineapple cottage. The home was clean are ready early. Management kept us I formed throughout the booking process and leading up to our arrival. AC worked great and private pool was the main event. Spent evenings cooling off after a day waking around town or relaxing on the beach. Thank you.

Manager's Response

Hi Phillip,

We appreciate your thoughtful review! It’s fantastic to hear that you had a great time in Key West and enjoyed the privacy, cleanliness, and especially the pool. We’re also glad the AC kept you cool and comfortable during your stay. We’d be delighted to host you again on your next trip.

Amazing

June 2024
, Ypsilanti, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Amazing!

Manager's Response

Hi Phillip,

Thank you for the kind review! We’re so happy that your stay was nothing short of amazing. We hope to have you back at Pineapple Cottage again soon!

Wonderful Place

May 2024
, Saint Peters, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location. Lots of privacy and quiet time when you need it. Will be back..

Manager's Response

Hi Gary,

Thanks for the wonderful review! We’re thrilled that you enjoyed the location and found the privacy and quiet exactly what you needed. We look forward to your return for more relaxation in Key West!

Another great trip....

April 2024
, Bartlett, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is our second time staying at Pineapple Cottage. We absolutely love this rental. It is in the heart of everything, yet so private at the same time. Everything you need is here. We will be back.

Manager's Response

Hi Mason,

Thank you for your fantastic review and for choosing Pineapple Cottage for a second time! It’s great to hear that you love the rental and the perfect balance of being in the heart of everything while maintaining privacy. We’d be happy to host you again for your third stay!

5 Days in Key West

April 2024
, Plymouth, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Pineapple Cottage is perfectly located just a half block from Duval. The cottage was exceptionally clean. Only negative was the beds, new mattresses would make the cottage perfect. Out door area was also very nice, with a grill and plenty of seating. We would definitely recommend this cottage to friends and family.

Manager's Response

Thank you for the wonderful review. I am happy to say that new mattresses have been ordered and have been replaced on April 16, 2024.

Pineapple Cottage

March 2024
, Gloucester, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a wonderful time at Pineapple cottage.
Great location, great pool, comfortable home and easy to reach property manager. Thank you.

Manager's Response

Hi Michele,

Thank you for the wonderful review! We’re thrilled that you enjoyed your stay, especially the location, pool, and comfort of the home. It’s great to know our team was helpful and responsive. We hope to welcome you back in the future!

Key West Rental

March 2024
, Warwick, RI United States

Overall
3
Property condition
2
Location
5
Cleanliness
3
Services from rental manager
5

The location of the cottage is perfect, close to everything but a bit away from the noise. The pool and yard is an adorable oasis. For the nightly price it would be reasonable to expect nicer beds, paint touch ups, repair of cracked stairs, repaired decking, replacement of torn patio furniture, etc.

Manager's Response

Thank you so much for sharing your feedback regarding the house. We truly appreciate your insights. Just to update you, we have a brand new mattress for the upstairs area on order, and our new lawn furniture is also scheduled for delivery very soon.


Living in Key West poses a unique challenge as we don't have local stores readily available, which means most items have to be ordered in advance. As our property serves as a transient home, we have to balance small repair projects around our guests' stays. Rest assured, we will address these repairs as soon as time allows.


Once again, thank you for choosing to stay with us. Your feedback helps us improve and provide a better experience for our guests. We look forward to welcoming you again in the future.

Another wonderful stay at Pineapple Cottage, Key West

March 2024
, Franklin, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Staying at the Pineapple Cottage allows you to have an effortless enjoyable vacation in Key West! It's central location allows you to walk wherever you want to go. No need to rent any type of transportation. The private pool retreat allows you to just relax when you choose to. This is our 3rd stay and we will be back for our 4th!

Manager's Response

Thank you, our repeat guests are truly appreciated.

A wonderful tranquil week in Key West

February 2024
, Grosse Pointe Park, MI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Preferred Properties was the best management company I have ever worked with in Key West. Thank you so much for the great communication, kind and friendly service.
The downstairs bed had seen better days, but okay for one person. otherwise the property was absolutely beautiful, quiet and so private. All the comforts of home were provided.

Manager's Response

Thank you for the nice comments and will work on replacing the guest mattress. All suggestions and comments are truly appreciated! Hope to have you back in the near future.

Birthday Surprise

December 2023
, Southport, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

If we ever go back to Key West, we are absolutely going to stay here. The house is private and in a perfect location. Thank you!

Adorable cottage

November 2023
, Belvidere, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This cottage is just adorable! Very spacious with bedrooms up and down. We loved the outdoor patio as we had coffee every morning out there. We would relax in the pool in the afternoon. Everything was within walking distance.

Great location!

October 2023
, Kaiser, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We enjoyed our stay so much! It is close to the busy Duval street, but at the same time feels very private. Great experience overall, although I would have proffered a heads up about a pool guy showing up and just walking though in the middle of the day - was very much unexpected :)

review

August 2023
, Dayton, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

good

review

August 2023
, Beavercreek, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

good

Hidden Gem

July 2023
, Bardstown, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Perfect location. Management was great. Pool was relaxing.

Great location

July 2023
, Wellington , FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This place is amazing. You can’t beat the location, walk to everything in minutes. The house and pool area were great. Definitely will be my go to place to rent.

Great house & location!

May 2023
, Warrensville, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Awesome!

Pineapple Cottage

May 2023
, Plsya del rey, CA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location Clean and well appointed. Enjoyed our stay. Group of 4, easily accommodated.

Private paradise

April 2023
, Palm Desert, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location, perfect layout for two couples, very private pool

Perfect Family Vacation

April 2023
, Rumson, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great Property! Had everything you could possibly need. Enjoyed Family time in the pool and the location was perfect!

Always LOVE Pineapple Cottage

March 2023
, Stony Brook, NY United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

Always LOVE staying at Pineapple Cottage. The place itself is awesome, and you can’t beat the location. The staff, especially this most recent time, was beyond friendly; really great.

Best location

March 2023
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We’ve stayed at this home several times. The location is great with several restaurants and shops in close walking distance. The layout is perfect for two couples. The outdoor space is exactly what we were looking for with a large pool and plenty of deck/seating space. Preferred Properties and Angela specifically are easy to work with and very responsive. We look forward to booking this place again.

Best location

March 2023
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We’ve stayed at this home several times. The location is great with several restaurants and shops in close walking distance. The layout is perfect for two couples. The outdoor space is exactly what we were looking for with a large pool and plenty of deck/seating space. Preferred Properties and Angela specifically are easy to work with and very responsive. We look forward to booking this place again.

Love the Pineapple Cottaage!

February 2023
, New Albany, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage is a great place! So close to Duval St. but you wouldn’t know it from the house. Love the pool and the grounds. We’ve stayed there 3 years in a row and would stay there again and again.

Location Location Location

January 2023
, Lawton, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great place and so easily accessible to everything. Definitely enjoyed the heated pool!

Secluded paradise

January 2023
, BEDFORD, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very private oasis in a busy town. Nicely appointed, clean VRBO with beautiful patio space and awesome heated pool. Great location for popular tourist destinations. Has it's own dedicated off-street parking space. Excellent communication with Preferred properties folks. Would highly recommend.

The best in key west

January 2023
, Arvada, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple cottage is amazing in every way.....clean, well appointed kitchen, great outdoor space and great location. The grocery store just a block away. close to duval for all the restaurants and bars but far enough away to have peace and guiet. We’ve stayed her 2 years in a row and hope to be back next year....love it !

Pineapple Cottage Love It! Didn’t want to leave it!

December 2022
, Burlington, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage has everything needed for a great getaway close to the Old Town hotspots yet quiet enough to relax by the pool and chill. We will definitely seek to stay again. Working the the staff from Preferred Properties was easy, open and concise communication!

Florida Keys getaway

November 2022
, Temecula, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage was a great location just off Duval. Enjoyed the pool in the evenings. Management was great. Highly recommend!

Pineapple Cottage

October 2022
, Tennessee, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Everything about this property was great. The location was perfect. The backyard is very secluded and the pool was wonderful for relaxing after a few hours of action on Duval street. The pool was clean and warm and totally private. The Preferred Properties office is very close and the people there were very helpful and professional. We will definitely stay here again.

Lovely home, friendly helpful staff.

October 2022
, Silverado, CA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location, close to everything! The staff at the rental agency was very communicative and helpful. The house was perfect for two couples and room for more. We enjoyed the pool too.

Wish I could give 10 stars!!!

October 2022
, Curwensville , PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This place was amazing from location to bedding to NO noise and ALL the privacy a person and family could need!. Everything was amazing! The staff at the office welcomed us when we were there early and Kevin was able to get us what we needed. Angela was a HUGE help as well- even keeping us posted after the Hurricane came through before we came down. Clean, TONS of space and convenient. Will definitely be coming back!!!!!

Best little hideaway in Key West

August 2022
, Westfield, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

Adorable cottage centrally located. very spacious. the outdoor area was spectacular, the concierge service was incredible. can’t wait to come back.

The BEST Vacation...round 2!

August 2022
, Havertown, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My husband and I along with my sister and her husband stayed at the cottage for a second time this summer and it was everything we hoped for! The property was very clean and very private. We loved hanging out in the pool and the location to Duval street can't be beat! The Preferred Properties team was also so helpful. kind and accommodating to our needs. We will definitely be back again!

Hidden Retreat

July 2022
, Murfreesboro, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We absolutely LOVED our time at this property. The location was perfect. Everything about the property was exceptional. The outdoor space was a relaxing retreat. Indoor space was clean, updated and had everything we needed for our stay. We can’t wait to come back and have already recommended this property to friends. Thank you for making our time in Key West special!

BEST LOCATION!!!

July 2022
, Tampa, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This Key West house was even better in person! So clean, so private, and best location to everything!!!! Will absolutely stay here again in the future.

Amazing cottage hide away

June 2022
, Dalton, GA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I dont know how many houses like this are hid away in Key West, but we are very fortunate to have found the Pineapple Cottage. Located so close to everything. Go walking along Duval, get a little sweaty, just come right back and jump in the pool! With your very own parking spot, located right behind the house, we never had to worry.

Don’t stay here

June 2022
, nashville, IN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Seriously I am concerned if I say just how much my girls and I enjoyed our stay the price will go up and availability will go down! Just a spectacular home in a perfect location! Old town Key West is so much fun for everyone! We can’t wait to return and hopefully stay at pineapple cottage...

Paradise in the Middle of Paradise

June 2022
, Southaven, MS US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage is a hidden gem. From the cozy comfortable cottage to the beautiful lush pool area. This is a great place to relax!

Pineapple Perfection

May 2022
, Mercerville, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great property ,Great location ,Awesome management team, we will definitely be back !

Pineapple Cottage

May 2022
, West Chester, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

As always Great stay at The Pineapple Cottage. Great location , clean. Can't wait for next year!!

Our spring get away

April 2022
, Paxton, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a wonderful experience staying at Pineapple Cottage. As nice as the interior was, the outside living space was magnificent. Except for sleeping inside, we were outside enjoying the pool. Definitely a place we would stay again and suggest to other people.

Pineapple Cottage

March 2022
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is one of our favorite houses to stay in. The location is fantastic, walkable to everything, 1/2 block from Duval, but very private. Highly recommend. The team at Preferred Properties is top notch.

Pineapple Cottage

March 2022
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is one of our favorite houses to stay in. The location is fantastic, walkable to everything, 1/2 block from Duval, but very private. Highly recommend. The team at Preferred Properties is top notch.

Peace and Quiet in the middle of it all

January 2022
, Lexington, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a lovely vacation at Pineapple Cottage. Everything lived up to the pictures and descriptions - which does not always occur. We loved the location, close to everything we wanted to do, yet quiet and private. The pool and deck were perfect for late afternoon relaxation. The only negative was the parking spot (which isn't always available at other properties). The bad thing was, it was next to trees, and evidently the local birds did not approve of our car, and showed their feelings by decorating it with their droppings. (Not sure how to fix that, but it was a negative...) We'd return in a heartbeat for our next visit to Key West!

Fabulous

January 2022
, Arvada, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Location...fabulous. Grocery store one block
Outdoor space...fabulous......grill...fabulous
Pool...fabulous
Kitchen ...fabulous....everything you could possibly need
Best place in Key West.....we stayed other places but none compare
No need to look further this place has it all...fabulous
Great customer service...Angela was also fabulous

Very Relaxing

December 2021
, Springfield, PA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Most enjoyable. Great location, Nothing like a Key West Christmas!

This is the spot!!

December 2021
, Ravenna, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Everything you need!! Location is perfect 1/2 block off Duval yet no noise. Block from coffee and store, both convenient. Nothing negative about this property. Already planning next year!!

Pineapple Cottage Rental

December 2021
, Plainfield , IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was very nice and well maintained. The area is also quiet and in a great location.

Great Oasis

November 2021
, Chagrin Falls, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We really enjoyed the Pineapple Cottage. It is located for easy access to bars, grocery, restaurants, and other attractions. We loved it!!

Key West Getaway

November 2021
, Melbourne, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our experience was such an smooth one from renting, arriving, our stay and our departure. The place is amazing! The location was just perfect. We were able to keep our vehicle parked off the street (which is a big thing considering the public parking situation). We walked just about anywhere we needed to go which was a blessing. We could walk to sunset each day!
For four adults, the accommodations were awesome and exactly what we hoped for. The pictures and the property matched well. Beds were comfortable, all appliances were in good working order, a/c was good and the full size washer and dryer was a great bonus!
We would rent this property again if it is available when we return to Key West. The management company is very professional and keeps you up to date as you get near to your stay.

Key West Getaway

November 2021
, Melbourne, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our experience was such an smooth one from renting, arriving, our stay and our departure. The place is amazing! The location was just perfect. We were able to keep our vehicle parked off the street (which is a big thing considering the public parking situation). We walked just about anywhere we needed to go which was a blessing. We could walk to sunset each day!
For four adults, the accommodations were awesome and exactly what we hoped for. The pictures and the property matched well. Beds were comfortable, all appliances were in good working order, a/c was good and the full size washer and dryer was a great bonus!
We would rent this property again if it is available when we return to Key West. The management company is very professional and keeps you up to date as you get near to your stay.

Relax

October 2021
, Athens, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great place to relax and enjoy all Key West has to offer. Location is perfect within a short walk to either end of Duval. We have stayed there many times and its always perfect. The pool and deck area seems like there is nothing around.

Pineapple cottage was excellent!

August 2021
, Colden, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple cottage is a great place to stay in Key West. It is totally private, Very clean and well appointed and in a great location! Preferred Properties Staff were very helpful and accommodating.

Awesome house

August 2021
, Seven fields, PA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was perfect! We went in August so it was super hot outside..... the pool was a godsend.
The house was neat and had everything we needed.
I am going to miss waking up and walking a few doors down to get my Cuban con leche coffee
We all loved are daily iguana visits!!!

Pineapple Cottage

July 2021
, Union, Ky United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Pineapple Cottage is perfect for a stay in Key West! So conveniently located but with loads of privacy and equipped with everything you need.

Great Stay

June 2021
, Austin, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved everything about the house. It was very comfortable and exactly as described. Very conveniently located and the pool was the perfect escape from the heat. We would definitely stay here again if we are in Key West.

Great Stay

June 2021
, Austin, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved everything about the house. It was very comfortable and exactly as described. Very conveniently located and the pool was the perfect escape from the heat. We would definitely stay here again if we are in Key West.

A hidden gem in a perfect location

June 2021
, Havertown, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We stayed here for five nights in late June. The house was very clean and the pool was amazing. It was a short walk to everything so we didn’t even rent bikes or a golf cart. We had a wonderful time here and hope to visit again in the future.

Absolutely magical property!

June 2021
, Greensboro, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a fantastic stay in this little oasis in the heart of Key West. The pool and landscaping were amazing and provided ample privacy and relaxation. The staff at Preferred Properties were top notch and attentive. Of all the vacation properties we have stayed at, this was by far the cleanest and most well-cared for property we have experienced. We will be back!

Pineapple Cottage is Fantastic!

June 2021
, Plymouth, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We loved our stay at the Pineapple Cottage in Key West! We are a family of two adults and two daughters 18 & 25 years old. The entire experience from the booking, arrival, the stay, and departure was handled in the best possible way by Preferred Properties on behalf of the owners. Such great communication and accessibility (even after hours). The location of the property is ideal; 1/2 block from Duval Street but completely secluded and private with a large (by Key West standards) private swimming pool surrounded by decks. You don't even know you are that close to the craziness of Duval Street when you are sitting by the pool in the back yard. There are breakfast places, coffee houses, restaurants, a small grocery store, and a liquor store all within 2 blocks of the property. The house itself is perfectly laid out and contained absolutely everything we needed during our 1 week stay. The property owners thought of everything! We rented bikes for the week to see the island and Preferred Properties even arranged that for us prior our visit. The property was clean when we arrived and is in good condition considering the amount of rentals they must have at this property all year long. I honestly can't come up with a complaint or downside to staying at this wonderful property. I will recommend that you bring bug spray because it was very buggy (mosquitos and gnats) at the property; however, that is probably just a function of the weather in Key West in June most likely. If there is ever any availability here in the near future, we will definitely come back to the Pineapple Cottage. Once you stay here, it will be your "go to" for lodging in Key West.

Florida Keys Getaway

June 2021
, Columbia, MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We took a 41st wedding anniversary trip with another couple who were celebrating their 50th birthdays. We spent a week in the Keys with our last 3 days at Pineapple Cottage. We definitely saved the best for last, although each of our 3 VRBO properties were wonderful in their own unique way. The location of Pineapple Cottage was awesome! Right in the middle of everything, yet it felt like a private hidden oasis! Well equipped and very comfortable property with its own pool!

The Best Cottage in Key West!

May 2021
, Pawleys Island, SC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The Pineapple Cottage was absolutely perfect!! It was centrally located, fully stocked, clean, spacious and the pool was an oasis. The owner was extremely accommodating and checked in frequently. We had the best time and we will be back! Thanks!!

Long overdue!

May 2021
, Fitchburg, MA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our group waited an extra year to visit Key West and we were not disappointed in our choice to stay at the Pineapple Cottage. The house was immaculate! The floor plan was ideal for traveling with another couple as it made it feel like two separate spaces. Every necessary utensil was provided in the kitchen. The pool and outdoor space were amazing and relaxing. We were just steps from Duval but in our own little oasis. We will definitely return!

Pineapple Cottage

April 2021
, West Chester, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Location, Location, Great place , clean , Can't wait to return next year

Great Stay in Pineapple Cottage

April 2021
, Plano, IL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time in Key West (this was our first time). The Pineapple Cottage was great! The pool was a savior. We were in it every day prior to going out and hitting the town mid-afternoon. Made several iguana friends each day in the backyard...

Lovely cottage in great location

April 2021
, Brentwood, TN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home was exactly as advertised. Well appointed and comfortable. The location is perfect - steps away from Duval but hidden away and very private. We will definitely return!

Lovely cottage in great location

April 2021
, Brentwood, TN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The home was exactly as advertised. Well appointed and comfortable. The location is perfect - steps away from Duval but hidden away and very private. We will definitely return!

Perfect oasis in old town

April 2021
, Lockhart, TX Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was our second time renting the Pineapple Cottage and once again it was perfect. The location, the pool, the quiet seclusion, and the cleanliness are excellent. If we come back to KW, we will definitely rent this cottage!

Perfect

April 2021
, Buffalo, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

House location could not have been better. The home had everything that you would need. Pool was clean and quite. Privacy was not an issue. I would rent this home again without a 2nd thought.

Key West vacation

March 2021
, St. Louis , MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had a great time and were extremely impressed by the Pineapple Cottage. On any future visits to Key West, we would only consider staying there again!

2nd Stay in Paradise at Pineapple Cottage!

March 2021
, Franklin, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our 2nd stay at Pineapple Cottage was better than our 1st visit back in 2017. The centralized location in Old Town is perfect! No need to rent a vehicle since everything is within a mile! The home and the private pool is truly a wonderful piece of paradise! Can't wait for our 3rd visit!!!

2nd Stay in Paradise at Pineapple Cottage!

March 2021
, Franklin, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our 2nd stay at Pineapple Cottage was better than our 1st visit back in 2017. The centralized location in Old Town is perfect! No need to rent a vehicle since everything is within a mile! The home and the private pool is truly a wonderful piece of paradise! Can't wait for our 3rd visit!!!

Key West - Pineapple Cottage

January 2021
, Scottsdale, AZ Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was a reschedule due to early 2020 COVID restrictions. The team at PPM assisted us in finding a new date and accomodating our new needs. The property was properly prepared and was well-equipped. This lead to a very enjoyable stay.

Our Thanksgiving Tradition

November 2020
, Reston, VA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had such a great Thanksgiving in 2019 at Pineapple Cottage we said we’d be back and we made it happen! The house was perfect for our family. Quiet, private and a beautiful backyard and pool. Here’s to our new tradition. We’ll be back in 2021!

Our Thanksgiving Tradition

November 2020
, Reston, VA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We had such a great Thanksgiving in 2019 at Pineapple Cottage we said we’d be back and we made it happen! The house was perfect for our family. Quiet, private and a beautiful backyard and pool. Here’s to our new tradition. We’ll be back in 2021!

The best place to stay in Key West!

November 2020
, Huntingburg, IN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My husband and I have stayed at Pineapple Cottage many times. We love the privacy, the pool and we simply feel very comfortable in the cottage! We loved the upgrades! Preferred Properties have always been very good to us, they are indeed number one when it comes to vacation rentals!

Manager's Response

Sammy, Thank you for your review and also thank you for your contributions to our community. Congrats on the Smart Ride! Very impressive. We look forward to your visit each year. You always help make our product even better with your perfect suggestions and your pleasant hints when we forgot the coffee maker after the upgrades. We are glad we were able to find one quickly for you because Cuban Coffee Queen every day, while amazing, may not be the best option for relaxing and recharging. We really appreciate your repeated business and it is becoming ever more wonderful getting to know you guys more. Great music was overheard anytime we were near the property! :-)

JUST WHAT WE NEEDED ❤️

July 2020
, JOHNSTOWN, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I cannot say enough great things about the staff at Pineapple...they are all amazing!! The house, the pool, and the location was perfect in every way! We rented a vehicle and only used it once to drive to Marathon to look at some properties. If you have no plans to drive anywhere save the money on the rental....the location is within walking distance to everything! We will be back very soon!!

Gem in the Heart of it All

July 2020
, Greenville, SC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent the first half of our vacation at the Pier House and actually preferred this property with its private pool, iguanas, beautiful floral landscape, dedicated parking space, well-appointed kitchen and great location to all in midtown Duval.

Manager's Response

Thank you, Roger! The Pier House is a fantastic property, thankfully you were able to also experience Pineapple Cottage and now know why so many people choose to stay in a vacation rental when visiting Key West. We hope you visit us again someday!

Fabulous !

June 2020
, Union, KY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Wonderful property, great location, and superior customer service from Preferred Properties

Manager's Response

Thank you John for your nice review. We appreciate our guests and always try to make sure they have a nice time!

Great house, and location!

March 2020
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We've been coming to Key West for the last 8 seasons. We normally rent from a different company, but they didn't have a home that would work. We couldn't have been happier with Preferred Properties, and Angela specifically. She was great to work with, and the house was one of the best we've stayed in. The location is awesome, and the pool was extremely private, which is what we wanted. We will for sure try to stay here again, if it's available on our next trip.

Great house, and location!

March 2020
, Ann Arbor, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We've been coming to Key West for the last 8 seasons. We normally rent from a different company, but they didn't have a home that would work. We couldn't have been happier with Preferred Properties, and Angela specifically. She was great to work with, and the house was one of the best we've stayed in. The location is awesome, and the pool was extremely private, which is what we wanted. We will for sure try to stay here again, if it's available on our next trip.

Outstanding rental experience

January 2020
, Brunswick, ME US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This rental experience was top-notch from the initial booking to the final departure. Staff was helpful and communication was excellent. Property was immaculate, and exactly as described in the summary. Best experience I've had renting a vacation property - I plan to return to the area every year, and wouldn't dream of using any other agency to help plan my stay.

Amazing Property and Location!!!!

December 2019
, Madison, WI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was exactly what we had hoped for and the location was even better than expected. We really enjoyed the pool and the proximity to Duval. The parking spot was an added bonus!

A Great Place to Stay!

December 2019
, Omaha, NE US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We enjoyed our stay at Pineapple Cottage! It was very neat and clean, exactly as the pictures show. We loved the pool and the fact that you could request to heat it. The cottage is close to shopping and restaurants. In a walks distance to everything we wanted to see. Excellent customer service from the property management. We felt very comfortable and valued as guests. We would love to stay here again in the future.

Best Thanksgiving Ever

November 2019
, Reston, VA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything

Best Thanksgiving Ever

November 2019
, Reston, VA Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything

Best Thanksgiving Ever

November 2019
, Reston, VA US

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything

Relaxing time

October 2019
, Lockhart, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our stay at Pineapple Cottage was just what we needed to get away from work for a few days. It is in a great location, peaceful outdoor space, and clean and quiet inside. The management tea;m was always available on answered all our questions quickly. We had a fantastic time and will be back!

Wonderful Oasis

October 2019
, North Wildwood, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This was a perfect location for our short visit, close enough to everything yet quiet. The backyard/ pool area is a beautiful spot to relax in, surrounded by palms, flowers and blue skies. The house was clean and had what we needed and the beds were very comfortable. Angela went above and beyond, responding quickly to our questions and had great recommendations. You won’t be disappointed!

Anniversary in Pardise

September 2019
, South Bend, IN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My husband I rented Pineapple Cottage for our 20th wedding anniversary and it was truly a paradise of our own. This property is in the BEST location with everything in walking distance. So close to Duval (1/2 block) and a block to grocery store (Fausta's). The house is tucked behind a business and you have your own little paradise. The house and pool were so clean. The property manager answered questions very quickly. We will definitely be visiting Pineapple Cottage again.

Pineapple Cottage Stay Review

August 2019
, Germantown, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The Pineapple Cottage is one of those hidden gems that you need to be told about. It is private and quiet in spite of being steps away from Duval Street and many of Key West's wonderful restaurants and bars. There is nothing negative to say about this property. We would come back in a heartbeat. Our stay coincided with Lobster Fest, and, if you've never attended, we recommend putting this celebration of food and life on your bucket list.

Manager's Response

Thank you for your review. We are elated that you enjoyed your stay. We agree, Lobsterfest is a delicious time to be here!

Pineapple cottage

July 2019
, Danbury, CT United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We loved this place. Close to Duvall street. Upstairs was perfect spot and separate for one group. Downstairs great too.

Great location

July 2019
, LITTLE ROCK, AR US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great location, nice pool, clean property

Manager's Response

We are grateful that you enjoyed your visit!

PINEAPPLE PARADISE!

July 2019
, Largo, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Super clean! Outstanding location and a close walk to everything. The layout was perfect for 2 couples. Completely separate living room areas on the upper and lower levels. Pool was incredible! We will definitely be staying here again on future visits!

PINEAPPLE PARADISE!

July 2019
, Largo+FL, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Super clean! Outstanding location and a close walk to everything. The layout was perfect for 2 couples. Completely separate living room areas on the upper and lower levels. Pool was incredible! We will definitely be staying here again on future visits!

PINEAPPLE PARADISE!

July 2019
, Largo, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Super clean! Outstanding location and a close walk to everything. The layout was perfect for 2 couples. Completely separate living room areas on the upper and lower levels. Pool was incredible! We will definitely be staying here again on future visits!

Pineapple Cottage Key West June 2019

June 2019
, Brighton, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Excellent home and location. management company exceptionally helpful!! Would highly recommend.

Pineapple Cottage - Key West

May 2019
, Waukegan, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This was our fourth stay at Pineapple Cottage so that tells you how much we like it. What we enjoy most is the privacy, the pool and the location, it's tucked away behind a store front in a commercial district about a half block from Duvall Street.

Although close to several businesses and Duvall, it's pretty quiet in the evening and at night. Since it's the only house in that area, there aren't any neighbors to bother you.

The pool is wonderful, it gets afternoon sun and is surrounded by a lush tropical garden. Outdoor speakers let you listen to your tunes while you float in the large (for Key West, approx. 15 by 20 feet) pool. After the swim you can tan in privacy.

The house is well equipped with everything you'll need for your stay. There is a stereo and the house has Direct TV feeding four TVs. The house could use a bit of an update but that true for most of Key West.

Overall, it's a great place to stay if you want to be close to the action on Duvall. We're already looking forward to our fifth visit.

Manager's Response

It is interesting that the hustle and bustle of Duval disappears the moment you enter the gate to the Pineapple Cottage. It is serenity back there and our repeat guests consistently cite the peaceful escape as their number one reason to go back to Pineapple! Fifth visit, coming up! How awesome is that? Thank you!

Pineapple Cottage Key West Stay

April 2019
, Tampa, Florida United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was our second time staying there. We were there 4 years ago. We love the location and when entering the back yard it is like entering a tropical oasis. Upon entering after 4, we were met with an air conditioning man fixing a leak that cleared up in a few days. The place is super clean and extremely well supplied. There seemed to be an extra amount of leaves and flowers at the bottom of the pool. Wish there was a rail to help you enter to pool. The deck gets super hot so we're your flip flops! Having a parking spot and opening made loading and unloading a breeze!

Awesome getaway for my wife and her sister

April 2019
, WILLIAMSTON, MI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage was perfectly located very close to all of the restaurants and fun on Duval. Yet, it was very quiet and allowed for comfortable relaxation as well. They had a great time.

My wife said the property management team was extremely responsive and very helpful. It couldn't have been better.

Awesome getaway for my wife and her sister

April 2019
, Williamston, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage was perfectly located very close to all of the restaurants and fun on Duval. Yet, it was very quiet and allowed for comfortable relaxation as well. They had a great time.

My wife said the property management team was extremely responsive and very helpful. It couldn't have been better.

Another Key West Sunset

February 2019
, Greensburg, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our 3rd year in Pineapple Cottage; love this little place. Everything was perfect as always. Great location to walk to everything. Pool perfect size for afternoons in the sun.

Another Key West Sunset

February 2019
, Greensburg, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our 3rd year in Pineapple Cottage; love this little place. Everything was perfect as always. Great location to walk to everything. Pool perfect size for afternoons in the sun.

Amazing Getaway

November 2018
, Madison Heights, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was the perfect place for an adult vacation. Tucked away we had complete privacy. The house is great and the private pool after a day of walking around town was the perfect end. We’ve already thought about reserving again for next year. It’s a great location, very close to Duval and many attractions. This was the best experience!

Amazing Getaway

November 2018
, Madison Heights, MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This house was the perfect place for an adult vacation. Tucked away we had complete privacy. The house is great and the private pool after a day of walking around town was the perfect end. We’ve already thought about reserving again for next year. It’s a great location, very close to Duval and many attractions. This was the best experience!

Perfect

October 2018
, Athens, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was the third time staying at the pineapple cottage and will be staying many more times.

Wonderful place

July 2018
, Garforth, GB United Kingdom

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This property is situated in a fantastic location just off Duval street. It is totally private and is close enough to all that Duval has to offer without being noisy. The property itself has everything you need for a self catering break. It is kept to a high standard and is spotlessly clean. I would have no hesitation in recommending this property to anyone.

Amazing

July 2018
, Ridgeland, SC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It was great. The house was wonderful. Preferred Properties always called and check on us. Can’t wait to stay again.

Wonderful, private, comfortable! Perfect!

July 2018
, Decatur, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We loved our stay at The Pineapple House. It had everything needed for a very comfortable stay, for 2 couples. Its just a short 1/2 block from Duval Street, so we walked everywhere we needed to go. We would definitely stay here again. We loved the pool and used it every day as it was very hot in Key West in July. Try Pineapple House! I guarantee you'll love it. We received excellent service from the management company, Preferred Properties. We will use them again for other locations.

30th Wedding Anniversary

July 2018
, cabot, AR United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent our 25th anniversary in Key West and decided to go back on our 30th. We had such a blast staying at Pineapple Cottage. The pool hit the spot!!! The place is secluded yet close to everything. We will stay here if we ever come back!!!!

Pineapple Cottage

May 2018
, Clyde, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We spent five nights at the Pineapple Cottage. We found the cottage to be cozy and clean. Having a living area, bedroom and bath on each level was convenient for our family. We enjoyed the pool and deck area on sunny days. The cottage is in easy walking distance to many good resturants and sights. Would happily recommend this property.

pineapple cottage

March 2018
, Sagaponack, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very private and comfortable

pineapple cottage

March 2018
, Sagaponack, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very private and comfortable

Ahhhhhhh

February 2018
, Media, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Tucked away from the hustle and bustle but so close to all the action. The pool area was a slice of heaven.

Repeat Stay at Pineapple Cottage

February 2018
, Greensburg, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Wonderful, relaxing place for our vacation. LOVE the pool for afternoon relaxing. Cottage is a beautiful little paradise. Perfect in every way. Only one thing we feel needs addressed and that is the mattresses. They are much too soft and upstairs bed had several pillow toppers on it, way too much for comfort. It was difficult to get into bed and get situated to sleep.

Repeat Stay at Pineapple Cottage

February 2018
, Greensburg, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Wonderful, relaxing place for our vacation. LOVE the pool for afternoon relaxing. Cottage is a beautiful little paradise. Perfect in every way. Only one thing we feel needs addressed and that is the mattresses. They are much too soft and upstairs bed had several pillow toppers on it, way too much for comfort. It was difficult to get into bed and get situated to sleep.

Fantasy Fest wknd

October 2017
, Neptune Beach, Fl United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Pineapple Cottage worked our perfectly for our Fantasy Fest weekend adventure!

First Time Rental of this Cottage

September 2017
, Rahway, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Interesting property, very private and comfortable. All amenities and utilities were superb with two exceptions. Wifi continued to issue an AT&T error in connecting with an assortment of addresses, even essential information websites during days before IRMA. Had to tether from cellphone to access the Key West Emergency Management page. The cable was very limited as well so streaming from a laptop may be your best source of entertainment for the limited time you spend indoors. Minor issue with ghost ants (very tiny ones) and common for the keys but nothing to be too concerned about. Every other aspect of the property was exceptional. Great location, privacy, condition of property and utilities all adequate and functional. The assigned parking space it a plus as well since KW is a parking nightmare without one.

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2 Bed
2 Baths
Sleeps 4

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Island Time

Check out this unique 5 Bedroom Key West Vacation Rental Complex – Island Time- with separate entrances to each cottage. Private swimming pool and upscale accommodations!

Location

801 Fleming Street
33040 Key West , FL
United States
24° 33' 30.5316" N, 81° 47' 57.0264" W
Florida US

Island Time

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Media

ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool

Unit Code: 801-807F

Island Time

Check out this unique 5 Bedroom Key West Vacation Rental Complex – Island Time- with separate entrances to each cottage. Private swimming pool and upscale accommodations!
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three bathrooms in 2 separate cottages with full amenities that has just been renovated and tastefully updated.The property can accommodate a maximum of 12 people. Both cottages are furnished beautifully, while retaining a charming vintage feel that this historical property affords us. Built in 1888 both cottages encompass one private, gated property with an oversized pool and waterfall, dining area, lounging, and grilling for your pleasure. The main house has two bedrooms and one full bathroom, living room, kitchen and dining area. There is one king bed in the oversized master bedroom and two twins in the guest room that can be converted to a king upon request. The second cottage has two bedrooms, both with queen beds, and one full bathroom, living room, dining room and kitchen plus a front porch with rocking chairs, which is a favorite spot for guests to enjoy morning coffee, or evening cocktails. From the porch, you can watch the Conch Train come by a few times a day and discuss our historical home on their tour. There is also a separate loft as well, with one king bed, two twin beds, a full bathroom, seating area and kitchenette. There is an outdoor shower plus 2 separate laundry areas. The proximity to Old Town is a real plus, being close to everything within walking distance: restaurants, shopping, Churches, beaches, multiple museums and live music. For the more adventurous vacationers, there is a bicycle rental shop one block away. Welcome to Island Time! Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Bedding Configurations: 801 Fleming-1 Queen in 1 Bdrm, 2 twins in second bdrm 807-1 Queen in each bdrm Loft-1 King and 2 twins 3D Walkthroughs available on the RealKeyWest website. 801 Home: 807 Home: The Loft: Monthly Rental Only (This property must be rented for 28 or more days by city ordinance) Small dogs 20 pounds or less will be accepted with a $200 non refundable fee. Maximum 2.
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03/01/2026 - 05/31/2026$770 /nt
03/01/2026 - 05/31/2026$866 /nt
03/01/2026 - 05/31/2026$23,610 /month
06/01/2026 - 08/31/2026$586 /nt
06/01/2026 - 08/31/2026$756 /nt
09/01/2026 - 11/30/2026$626 /nt
09/01/2026 - 11/30/2026$18,769 /month
09/01/2026 - 11/30/2026$18,775 /month
12/01/2026 - 02/28/2027$856 /nt
5.0000
(2 Review)

Happy in Key West

March 2022

Overall
5

This property was picture perfect. Each home has its own unique quality allowing everyone to be together, or get some quiet time. The cottage with the front porch was a favorite for morning coffee and afternoon cocktails. All 5 bedrooms had extremely comfortable beds. The pool area is a great gathering place to swim during the day, or BBQ at night. With 2 separate homes, with 2 separate kitchens, dining rooms, living rooms and laundry, as well as separate baths plus the loft with its private bath and sitting area, as 5 couples we were so comfortable and not on top of each other. The loft was a definite favorite. Being able to walk to the wharf and Duval is definitely a plus. There were so many great restaurants close by, as well as the market in walking distance. A month isn't long enough! We will be returning for sure:)

Key West Vacation

June 2019

Overall
5

My experience renting this property was great! The location is perfect - you could not ask for easier access to Duvall. Preferred Properties is always only a phone call away if needed. The property was just as advertised and beautiful.

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5 Bed
3 Baths
Sleeps 12

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Tranquility

Tranquility is an adorable 3 bedroom 3 bath home with a tropical setting.

Location

1308 Newton Street
33040 Key West , FL
United States
24° 33' 32.5476" N, 81° 47' 29.8392" W
Florida US

Tranquility

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Peace

Reviewed by Unknown on 2025-01-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very peaceful home and very clean.

Tranquility Stay

Reviewed by Deborah K. on 2022-03-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Immaculate 3-bedroom, 3-bath home with a fabulous private backyard deck and pool. The kitchen was well stocked with everything you’d ever need. Parking out front was no issue. Preferred Properties had excellent communication and responded quickly to our needs.

January Escape

Reviewed by Holly S. on 2022-02-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The property was just as described. We had a wonderful time and would book this house again. The property managers were quick to respond to any questions or issues that arose.

Paradise found

Reviewed by John R. on 2021-04-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Wonderful little house with everything you need to enjoy the conch life! Quiet, simple, and away from the noise of everyday life, 1308 Newton is a gift. The house the pool , the location and the great staff made this trip the best ever.

Second year staying at Tranquility!

Reviewed by Unknown on 2020-04-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
March was our second year staying at Tranquility. The house is very comfortable. The pool and back yard is very nice also. Location is a nice ride from Duval, but it’s easy to get to any part of Key West. Parking is always available. This year was a little different due to the covid-19. But, we will be back next year.

Wonderful!

Reviewed by Unknown on 2019-04-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
On arrival for our month stay, we found there was a parking space right in front of the house for our car. The house was clean and the backyard was beautiful. The property manager was quick to respond and very helpful. We bike everywhere so nothing was to far away. The street was very quit and neighbors very friendly. We have booked for 2020.
Manager response on 2019-05-28 - Response from Preferred Properties Management LLC
We enjoyed having you visit with us at Tranquility and are excited that you are coming back next year. The Meadows neighborhood is perfect for those seeking a quiet neighborhood but still want to be close enough to all the fun! Your review was a good reminder! Thank you!

Media

  • https://www.realkeywest.com/key-west-vacation-rentals/tranquility

TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest

Unit Code: 1308N

Tranquility

Tranquility is an adorable 3 bedroom 3 bath home with a tropical setting.
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom home is the perfect escape for those seeking peace and relaxation. As soon as you step inside, you'll be struck by the bright and spacious living room that flows into a fully equipped kitchen. French doors open to a deck and private pool, surrounded by palm trees and tropical landscaping for added privacy. Upstairs, you'll find two cozy bedrooms and an additional bathroom. Linens are provided for your comfort and convenience. This property is just seven blocks from the "Famous" Duval Street, making it the perfect location for those who want to be close to the action while enjoying a peaceful retreat. On-street parking is available for your convenience. Free WiFi is included, so you can stay connected while you relax. The estimated square footage of this home is 1320 sqft, providing plenty of space for you and your guests to spread out and make yourselves at home. Small pets may be considered, so feel free to bring your furry friends along for the vacation. Please note that Tranquility is available for monthly rentals, with a minimum stay of 28 days. Don't miss out on the opportunity to experience the tranquility and serenity of this beautiful vacation rental. Book your stay at Tranquility today and start planning your dream vacation! Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
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DatesPrice
03/01/2026 - 05/31/2026$468 /nt
03/01/2026 - 05/31/2026$482 /nt
06/01/2026 - 08/31/2026$481 /nt
06/01/2026 - 08/31/2026$538 /nt
09/01/2026 - 11/30/2026$459 /nt
09/01/2026 - 11/30/2026$645 /nt
12/01/2026 - 02/28/2027$759 /nt
12/01/2026 - 02/28/2027$993 /nt
03/01/2027 - 05/31/2027$658 /nt
03/01/2027 - 05/31/2027$964 /nt
5.0000
(7 Review)

Peace

November 2024
, West Newbury, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very peaceful home and very clean.

Tranquility Stay

February 2022
, Menomonee Falls, WI US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Immaculate 3-bedroom, 3-bath home with a fabulous private backyard deck and pool. The kitchen was well stocked with everything you’d ever need. Parking out front was no issue. Preferred Properties had excellent communication and responded quickly to our needs.

January Escape

January 2022
, Macon, GA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was just as described. We had a wonderful time and would book this house again. The property managers were quick to respond to any questions or issues that arose.

January Escape

January 2022
, Macon, GA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property was just as described. We had a wonderful time and would book this house again. The property managers were quick to respond to any questions or issues that arose.

Paradise found

January 2021
, New York, NY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Wonderful little house with everything you need to enjoy the conch life! Quiet, simple, and away from the noise of everyday life, 1308 Newton is a gift. The house the pool , the location and the great staff made this trip the best ever.

Wonderful!

March 2019
, Southport, NC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

On arrival for our month stay, we found there was a parking space right in front of the house for our car. The house was clean and the backyard was beautiful. The property manager was quick to respond and very helpful. We bike everywhere so nothing was to far away. The street was very quit and neighbors very friendly. We have booked for 2020.

Manager's Response

We enjoyed having you visit with us at Tranquility and are excited that you are coming back next year. The Meadows neighborhood is perfect for those seeking a quiet neighborhood but still want to be close enough to all the fun! Your review was a good reminder! Thank you!

Wonderful!

March 2019
, Southport, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

On arrival for our month stay, we found there was a parking space right in front of the house for our car. The house was clean and the backyard was beautiful. The property manager was quick to respond and very helpful. We bike everywhere so nothing was to far away. The street was very quit and neighbors very friendly. We have booked for 2020.

Manager's Response

We enjoyed having you visit with us at Tranquility and are excited that you are coming back next year. The Meadows neighborhood is perfect for those seeking a quiet neighborhood but still want to be close enough to all the fun! Your review was a good reminder! Thank you!

Leave a Review
3 Bed
3 Baths
Sleeps 6

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Peachy Keen

Welcome to Peachy Keen. A beautiful 3 bedroom 3 bath home with a private pool, off-street parking, and a bonus cabana.

Location

619 Thomas Street
33040 Key West , FL
United States
24° 33' 10.62" N, 81° 48' 13.446" W
Florida US

Peachy Keen

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Perfect home in paradise

Reviewed by Jeannine K. on 2025-06-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Peachy Keen is the perfect place! The pictures and virtual tour were spot-on. There were plenty of kitchen utensils, spices, and amenities for cooking at home. I love that the bedrooms are separated from each other (one bedroom to the right of the kitchen, the other to the left of the kitchen). There is also a small office space that was perfect for the few days I had to work while visiting. The pool was very spacious, and there is a large driveway (both rare in KW). We did not use the pool house, but it seemed bigger and brighter than it did in the pictures. Last but not least, the property manager was amazing! Angela was very attentive and quick to respond. She even helped us find our next spot for 2026 while we were there. If you want to be close to the Green Parrot, the Truman Waterfront and Blue Heaven, this is the place for you!

Great vacay in Key West

Reviewed by Lena F. on 2025-03-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Outstanding. And Phil the property manager could not have been more friendly, caring and professional.

April 2024 Key West Stay

Reviewed by Diane B. on 2024-05-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
What a beautiful place to stay. And the location was wonderful. Just a few blocks from the free bus to locations all around Key West, near Truman Waterfront Park and the greatest food, resteraunts and entertainment. Only a block from the Green Parrot and two blocks from Duval Street. Best location we stayed in many years. The home was well layed out giving you privacy and areas to be together too. The porches were comfortable and the pool was great. We definately won't hesitate to come back to Peachy Keen. Thank you Preferred Properties.

It was just peachy

Reviewed by Susan W. on 2023-05-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We rented for the month and really like the accommodations. The rooms were spacious and nicely furnished and the kitchen was especially well-equipped. The outdoor space was very generous and the grill was a wonderful asset.

Review of July 2022 Stay at Peachy Keen

Reviewed by Jerry J. on 2022-08-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Peachy Keen is a terrific Key West destination. I and my family have stayed here two years in a row and are planning to make it three! The house is roomy and comfortable, and the backyard and pool are a slice of paradise. The house is a short walk from restaurants and Duvall Street, yet far enough away so that I can have privacy when I want it. Preferred Properties, which I have had a relationship with for decades, is a joy to work with. Peachy Keen feels like home to me. Can't wait to get back.

Great retreat!

Reviewed by Matthew W. on 2022-06-06
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house was great and in a great location. The TV was difficult to understand so we just used our netflix.

Keen on Peachy Keen

Reviewed by Angela F. on 2022-03-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We love Peachy Keen! If you need a rental that can give you an escape and allow you to spend time together with extended family, this house is the one. We loved that the house had great shared spaces and an ability to retreat to your room for some of your downtime.


Peachy Keen's location is perfect. It is blocks away from some of our favorite restaurants in Key West; it is also close to the best beach in Key West, Fort Zachary. Yet it is located far enough away that you can retreat home to Peachy Keen when you are done for the day. We would spend days going on outings, then head home for afternoon naps and lounging by the pool, then back out for evening outings.


We have no complaints from our time; The Management staff answered any questions we had immediately after texting. It was so convenient to be able to text them any of my questions or concerns; it made me feel like I was not a bother. All in all, we enjoyed our stay due to so much I didn't even think about until writing this review: a clean house, a great location, a responsive staff, a warm pool, and a private area. So I can genuinely say we are very keen on Peachy Keen

Perfection with a hint of space travel

Reviewed by Trent L. on 2022-02-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This vacation home was our first time renting a home for an entire month, and we embraced everything the house offered, including the tasteful hints of Star Wars scattered throughout.
The house is in a fantastic location, just a block away from the Green Parrott and two blocks away from Duval Street. Nothing seemed too far. The pool was great, the backyard had a nice deck with a large gas grill, and the outdoor furniture was perfect for entertaining.
We hadn’t realized how easily the home could accommodate two couples with different ways to take in Key West. The second large bedroom has its own front door making it easy for one pair to stay out a bit later and not cause any disruption to those of us who went to bed early.
It took us a little longer to drive down than we expected, so the parking space was appreciated, but honestly, we used the car just two times while we were there.
The management company was exceptionally helpful and answered any questions we had. They had an excellent knowledge of Key West and even booked us an electric golf cart the week our oldest was in town.
A special shout-out to Angela, who put us at ease when we accidentally broke the coffee carafe on day 4. She replaced it the same day and explained how the damage plan we purchased provided coverage for this scenario.
The house has three bedrooms in the main home, two of which have their own bathroom. The third bedroom shares its bathroom with the central part of the house. The back cottage/pool house has a pull-down bed, a small fridge, and a toilet, transforming the space based on your need.
The kitchen has a great set of dishware and cookware, affording one the ability to prepare meals from home when you need a break from Key West’s phenomenal restaurants.
I look forward to visiting again as the experience was out of this world! I am now home and am glad I could relax for the month. The Force is strong with us!

Review of Peachy Keen

Reviewed by Jerry J. on 2021-09-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The best house I've rented on Key West. Nothing negative to say. The property was well maintained, clean, and just the right size. Its location was perfect: close to restaurants, watering holes, and Duval Street. Preferred Properties staff was responsive when anything needed to be brought to its attention. I will rent this place again. And again.

Peachy Keen Private Heated Pool, Cabana, & Prime Location Truman Annex!

Unit Code: 619T

Peachy Keen

Welcome to Peachy Keen. A beautiful 3 bedroom 3 bath home with a private pool, off-street parking, and a bonus cabana.
This beautiful home has 3 bedrooms and 3 baths in the main house with a bonus cabana. There is a private and heated pool, a separate entrance for one of the bedrooms, and a pool cabana that houses the 4th bedroom.  The property, situated in the heart of Key West, is located just outside the Truman Annex neighborhood, making it a very convenient location for all that Key West has to offer.   * 2 Blocks from Duval * a short bike ride to the beach of Fort Zachary State Park * and very close to some of the more interesting bars and restaurants on the island. When you enter Peachy Keen, you will be greeted with a large open-concept living room and eat-in kitchen.  The back multi-level entertainment space has a gas grill, a private-heated pool, and a bonus pool cabana. The main house has three bedrooms.  The master is off the kitchen, to the right.  It has an en-suite bathroom and a large walk-in closet.  The bed is adjustable and has doors out onto the backyard deck, a constant reminder of the Key West lifestyle. The second bedroom is to the left of the kitchen.  This bedroom has a separate property entrance, which makes it perfect if some of the party members wish to stay out later and not be a disturbance when they return home.  This bedroom also has its own en-suite and has a door to the backyard deck area and pool. The third bedroom is to the right of the main home's front entrance and is furnished with a sleeper sofa.  It shares the bathroom with the home's living room. The 4th bedroom is in a bonus cabana out back near the pool.  It has a queen-sized pull-down (Murphy-style) bed.  There is a toilet, but not a separate bathroom. This cabana is a perfect pool house due to its toilet and a small kitchenette with a sink and small refrigerator. There is also an outdoor shower completing this perfect Key West backyard. As you can imagine, this home can be divided up for maximum privacy.  Another couple can easily share the home, knowing they can come and go as they please. The back deck is covered, so you can enjoy eating outside, regardless of the weather. Go down one level and enjoy the Sun on the lower deck by the pool(which can be heated in the wintertime).  The house has a propane gas grill to cook your fresh catch of the day. This home also has an oversized parking spot, and again, the house can be accessed by two different entrances. Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. Monthly Rental Only Dogs accepted Towels, linens, bedding - all provided Free Wi-Fi Throughout w/Amazon Echo Private heated Pool Driveway Parking Washer/Dryer Great Downtown Location Iron and Ironing Board Kitchen: Refrigerator with Ice Maker Coffee maker Blender Toaster Wine Fridge Cookware Counter-height bar chairs and eat-in kitchen Lots of cabinet space
April 2026
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DatesPrice
03/01/2026 - 05/31/2026$379 /nt
03/01/2026 - 05/31/2026$446 /nt
03/01/2026 - 05/31/2026$13,015 /month
06/01/2026 - 08/31/2026$406 /nt
06/01/2026 - 08/31/2026$446 /nt
09/01/2026 - 11/30/2026$421 /nt
09/01/2026 - 11/30/2026$506 /nt
09/01/2026 - 11/30/2026$15,169 /month
09/01/2026 - 11/30/2026$15,175 /month
12/01/2026 - 02/28/2027$506 /nt
12/01/2026 - 02/28/2027$521 /nt
12/01/2026 - 02/28/2027$15,184 /month
12/01/2026 - 02/28/2027$15,190 /month
03/01/2027 - 05/31/2027$393 /nt
03/01/2027 - 05/31/2027$521 /nt
4.8333
(12 Review)

Perfect home in paradise

April 2025
, Columbus, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Peachy Keen is the perfect place! The pictures and virtual tour were spot-on. There were plenty of kitchen utensils, spices, and amenities for cooking at home. I love that the bedrooms are separated from each other (one bedroom to the right of the kitchen, the other to the left of the kitchen). There is also a small office space that was perfect for the few days I had to work while visiting. The pool was very spacious, and there is a large driveway (both rare in KW). We did not use the pool house, but it seemed bigger and brighter than it did in the pictures. Last but not least, the property manager was amazing! Angela was very attentive and quick to respond. She even helped us find our next spot for 2026 while we were there. If you want to be close to the Green Parrot, the Truman Waterfront and Blue Heaven, this is the place for you!

Great vacay in Key West

February 2025
, Wildwood, NJ US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Outstanding. And Phil the property manager could not have been more friendly, caring and professional.

Review of April 2024 stay at Peachy Keen

April 2024
, New Cumberland , Pa Usa

Overall
5

What a beautiful place to stay. And the location was wonderful too. Just a few blocks from the free bus to locations all around Key West. Definitely the best location for us. Near the bus and Truman Waterfront Park and the best restaurants and entertainment in Key West. The home was well layed out with places to be together yet sometimes be on your own. The porches were comfortable and the pool was great. We definitely won’t hesitate to return to Peachy Keen. Thank you also to Preferred Properties for the smooth check in and check out.

April 2024 Key West Stay

April 2024
, New Cumberland, PA Unknown

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5

What a beautiful place to stay. And the location was wonderful. Just a few blocks from the free bus to locations all around Key West, near Truman Waterfront Park and the greatest food, resteraunts and entertainment. Only a block from the Green Parrot and two blocks from Duval Street. Best location we stayed in many years. The home was well layed out giving you privacy and areas to be together too. The porches were comfortable and the pool was great. We definately won't hesitate to come back to Peachy Keen. Thank you Preferred Properties.

It was just peachy

April 2023
, Rye, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We rented for the month and really like the accommodations. The rooms were spacious and nicely furnished and the kitchen was especially well-equipped. The outdoor space was very generous and the grill was a wonderful asset.

Review of July 2022 Stay at Peachy Keen

June 2022
, Germantown, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Peachy Keen is a terrific Key West destination. I and my family have stayed here two years in a row and are planning to make it three! The house is roomy and comfortable, and the backyard and pool are a slice of paradise. The house is a short walk from restaurants and Duvall Street, yet far enough away so that I can have privacy when I want it. Preferred Properties, which I have had a relationship with for decades, is a joy to work with. Peachy Keen feels like home to me. Can't wait to get back.

Great retreat!

April 2022
, POLAND SPRING, ME United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was great and in a great location. The TV was difficult to understand so we just used our netflix.

Great retreat!

April 2022
, Poland Spring, ME US

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was great and in a great location. The TV was difficult to understand so we just used our netflix.

Keen on Peachy Keen

February 2022
, Broad Ripple, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We love Peachy Keen! If you need a rental that can give you an escape and allow you to spend time together with extended family, this house is the one. We loved that the house had great shared spaces and an ability to retreat to your room for some of your downtime.


Peachy Keen's location is perfect. It is blocks away from some of our favorite restaurants in Key West; it is also close to the best beach in Key West, Fort Zachary. Yet it is located far enough away that you can retreat home to Peachy Keen when you are done for the day. We would spend days going on outings, then head home for afternoon naps and lounging by the pool, then back out for evening outings.


We have no complaints from our time; The Management staff answered any questions we had immediately after texting. It was so convenient to be able to text them any of my questions or concerns; it made me feel like I was not a bother. All in all, we enjoyed our stay due to so much I didn't even think about until writing this review: a clean house, a great location, a responsive staff, a warm pool, and a private area. So I can genuinely say we are very keen on Peachy Keen

Perfection with a hint of space travel

January 2022
, Saugus, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This vacation home was our first time renting a home for an entire month, and we embraced everything the house offered, including the tasteful hints of Star Wars scattered throughout.
The house is in a fantastic location, just a block away from the Green Parrott and two blocks away from Duval Street. Nothing seemed too far. The pool was great, the backyard had a nice deck with a large gas grill, and the outdoor furniture was perfect for entertaining.
We hadn’t realized how easily the home could accommodate two couples with different ways to take in Key West. The second large bedroom has its own front door making it easy for one pair to stay out a bit later and not cause any disruption to those of us who went to bed early.
It took us a little longer to drive down than we expected, so the parking space was appreciated, but honestly, we used the car just two times while we were there.
The management company was exceptionally helpful and answered any questions we had. They had an excellent knowledge of Key West and even booked us an electric golf cart the week our oldest was in town.
A special shout-out to Angela, who put us at ease when we accidentally broke the coffee carafe on day 4. She replaced it the same day and explained how the damage plan we purchased provided coverage for this scenario.
The house has three bedrooms in the main home, two of which have their own bathroom. The third bedroom shares its bathroom with the central part of the house. The back cottage/pool house has a pull-down bed, a small fridge, and a toilet, transforming the space based on your need.
The kitchen has a great set of dishware and cookware, affording one the ability to prepare meals from home when you need a break from Key West’s phenomenal restaurants.
I look forward to visiting again as the experience was out of this world! I am now home and am glad I could relax for the month. The Force is strong with us!

Living the good life in Key West

October 2021
, Chicago, IL USA

Overall
5

I had the time of my life at this perfect getaway in the perfect location in paradise! No need for transportation other than Uber to airport because everything is walking distance, including groceries, restaurants and sites to see. You could comfortably sleep 8 and there is a nice living room/kitchen combo for hosting pre-party parties! I used the deck overlooking the pool for WFH, but it was hard to focus on work with so much to do nearby. Make sure you spend time at Ft. Zachary Taylor Beach, a 15 minute walk from Peachy Keen!

Review of Peachy Keen

August 2021
, Germantown, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The best house I've rented on Key West. Nothing negative to say. The property was well maintained, clean, and just the right size. Its location was perfect: close to restaurants, watering holes, and Duval Street. Preferred Properties staff was responsive when anything needed to be brought to its attention. I will rent this place again. And again.

Leave a Review
4 Bed
3.5 Baths
Sleeps 7

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Shady Palms

Enjoy this beautiful 2 bedroom 2 1/2 baths pool home in the lovely Key West section of Meadows Manor

Location

1415 Petronia Street
33040 Key West , FL
United States
24° 33' 34.128" N, 81° 47' 25.5804" W
Florida US

Shady Palms

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Great house in a quiet neighborhood

Reviewed by Unknown on 2025-04-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My husband and I recently rented Shady Palms for an extended stay and thoroughly enjoyed our time. It is located in The Meadows, which is a neighborhood of Key West residents so it is more quiet and friendly. The house is about a 15 minute walk to Mallory Square or to the Southernmost hotel area. The house is well furnished and has plenty of linens. The kitchen has more than the basic kitchen equipment, dishes, and pots/pans. We did rent a car for the month and easily found parking in front of the house. Altogether a good rental experience.

Shady Palms Review

Reviewed by Lauren K. on 2025-03-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
A wonderful home in a great location. Couldn't be happier with this property or with Preferred Properties.

Another stay in paradise

Reviewed by Unknown on 2024-03-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had another great stay at Shady Palms. The house has everything you need and more. The Meadows is a lovely, quiet neighborhood,, great for walking and biking. The “nightlife” of Duval Stret is a short walk away. The team at Preferred Properties is very friendly and responsive. 5 Stars!
Manager response on 2024-03-21 - Response from Preferred Properties Management LLC
Thank you, we appreciate our Repeat guests!

Perfection

Reviewed by Unknown on 2023-03-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We could not have been happier. The house is perfect; beautifully appointed and fully equipped. The neighborhood is quiet but you are easy walking distance from everything Key West has to offer. Preferred Properties could not have been more professional and easy to deal with.

Great, Cozy Neighborhood

Reviewed by Sammy S. on 2022-12-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our stay in Shady Palms was a wonderful experience! I’ve been leasing rentals through Preferred Properties for many years. I’ve never been disappointed! I highly recommend this rental company! 5 stars!

PERFECT KEY WEST VACATION RENTAL

Reviewed by FRANK C. on 2022-09-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The property could not have been more perfect! The pictures provided online are exactly what the house and property look like. Everything was clean and very well organized with every item you might need. The backyard was wonderful with the pool and privacy provided by the vegetation. The management company was quick to respond to any question or request. Highly recommend!

Shady Palms

Reviewed by Chris J. on 2022-02-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very nice place in a quite area of Key West but still accessible to most activities.

Welcome to the Shady Palms - Private Pool - 2 Bdrm, 2.5 baths

Unit Code: 1415P

Shady Palms

Enjoy this beautiful 2 bedroom 2 1/2 baths pool home in the lovely Key West section of Meadows Manor
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your fresh caught fish with enough room to seat four at the countertop. The master has a queen bed with its own ensuite that has a shower with multiple heads for a very luxurious shower. The guest room has two twins (that can be converted to a king) and it's own ensuite bathroom. This bathroom does have a shower/bath combination. Both bedrooms have walk in closets. The backyard has its own private pool and can be heated during our Winter months if needed. There is a table for 4 to eat al dente if preferred and two lounge chairs to get your tan on. This home does come with off street parking and a driveway for a medium sized vehicle. Come, enjoy a month in this beautiful Key West Home! Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
April 2026
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DatesPrice
03/01/2026 - 05/31/2026$401 /nt
03/01/2026 - 05/31/2026$430 /nt
03/01/2026 - 05/31/2026$12,180 /month
06/01/2026 - 08/31/2026$231 /nt
06/01/2026 - 08/31/2026$401 /nt
09/01/2026 - 11/30/2026$236 /nt
09/01/2026 - 11/30/2026$371 /nt
09/01/2026 - 11/30/2026$10,855 /month
09/01/2026 - 11/30/2026$10,858 /month
12/01/2026 - 02/28/2027$381 /nt
12/01/2026 - 02/28/2027$531 /nt
12/01/2026 - 02/28/2027$11,565 /month
12/01/2026 - 02/28/2027$11,575 /month
03/01/2027 - 05/31/2027$454 /nt
03/01/2027 - 05/31/2027$531 /nt
5.0000
(10 Review)

Shady Palms

August 2022

Overall
5

PERFECT KEY WEST RENTALThe property could not have been more perfect. The pictures provided online are exactly what the house and property look like. Everything was clean and very well organized with every item you might need. The backyard was wonderful with the pool and privacy provided by the vegetation. The management company was quick to respond to any question or request. Highly recommend

Great house in a quiet neighborhood

March 2025
, New Buffalo, MI United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

My husband and I recently rented Shady Palms for an extended stay and thoroughly enjoyed our time. It is located in The Meadows, which is a neighborhood of Key West residents so it is more quiet and friendly. The house is about a 15 minute walk to Mallory Square or to the Southernmost hotel area. The house is well furnished and has plenty of linens. The kitchen has more than the basic kitchen equipment, dishes, and pots/pans. We did rent a car for the month and easily found parking in front of the house. Altogether a good rental experience.

Shady Palms Review

February 2025
, Swarthmore, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

A wonderful home in a great location. Couldn't be happier with this property or with Preferred Properties.

Shady Palms Review

February 2025
, Swarthmore, PA United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

A wonderful home in a great location. Couldn't be happier with this property or with Preferred Properties.

Another stay in paradise

January 2024
, BOZMAN, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had another great stay at Shady Palms. The house has everything you need and more. The Meadows is a lovely, quiet neighborhood,, great for walking and biking. The “nightlife” of Duval Stret is a short walk away. The team at Preferred Properties is very friendly and responsive. 5 Stars!

Manager's Response

Thank you, we appreciate our Repeat guests!

Perfection

January 2023
, BOZMAN, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We could not have been happier. The house is perfect; beautifully appointed and fully equipped. The neighborhood is quiet but you are easy walking distance from everything Key West has to offer. Preferred Properties could not have been more professional and easy to deal with.

Perfection

January 2023
, BOZMAN, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We could not have been happier. The house is perfect; beautifully appointed and fully equipped. The neighborhood is quiet but you are easy walking distance from everything Key West has to offer. Preferred Properties could not have been more professional and easy to deal with.

Great, Cozy Neighborhood

November 2022
, Huntingburg, Indiana United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Our stay in Shady Palms was a wonderful experience! I’ve been leasing rentals through Preferred Properties for many years. I’ve never been disappointed! I highly recommend this rental company! 5 stars!

PERFECT KEY WEST VACATION RENTAL

August 2022
, OSPREY, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The property could not have been more perfect! The pictures provided online are exactly what the house and property look like. Everything was clean and very well organized with every item you might need. The backyard was wonderful with the pool and privacy provided by the vegetation. The management company was quick to respond to any question or request. Highly recommend!

Shady Palms

December 2021
, Bowling Green, KY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Very nice place in a quite area of Key West but still accessible to most activities.

Leave a Review
2 Bed
2.5 Baths
Sleeps 4

Search Availability

Heavenly Hideaway

This beautifully unique private pool home is a hidden treasure. Heavenly Hideaway is located across the street from our Historic Key West Cemetery and is in a quiet neighborhood. A plus to this home is it comes with parking for 2 small cars or large truck.

Location

917 Angela Street
33040 Key West , FL
United States
24° 33' 26.046" N, 81° 47' 46.1292" W
Florida US

Heavenly Hideaway

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Year 3 at the Heavenly Hideaway

Reviewed by Kathryn H. on 2025-03-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My family and I spent the month of February at the Heavenly Hideaway for the third year in a row and it was truly a perfect experience. The location is unbeatable – we were able to walk everywhere, from grocery stores to fantastic bars and restaurants.

The house itself is charming and well-maintained, with all the amenities we needed for a comfortable stay. The highlight for our family was the pool – my grandson absolutely loved swimming every day, and it became a special part of our routine.

If you’re looking for a peaceful yet central spot to enjoy Key West, this is it. We can’t wait to return next year!

holiday cottage

Reviewed by melissa g. on 2024-04-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
wonderful
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi, Thank you for your wonderful review! We’re thrilled that you enjoyed your stay at Heavenly Hideaway and found everything to be perfect. We hope to welcome you back again soon!

Quite nice

Reviewed by Unknown on 2024-02-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We loved the privacy combined with a great location. The porch could use a little trimming so as to be able to interact with people strolling by.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi, Thank you for your kind review and for sharing your feedback about the porch. We're happy to hear that you loved the privacy and the location. We’ll definitely take your suggestion about trimming the porch foliage into consideration to enhance the guest experience. We hope to welcome you back again soon!

The name says it all!

Reviewed by Kathryn H. on 2023-03-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We couldn't be happier with our stay at Heavenly Hideaway. Our family of 5 were very comfortable and never felt as though we were crowded at all. We enjoyed our meals on the covered porch surrounded by palm trees and warm breezes. Who could ask for more?
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Kathryn, Thank you for your fantastic review! We’re so happy to hear that your family had a wonderful time and enjoyed all the spacious gathering areas at Heavenly Hideaway. It’s also great to know our team was quick and efficient in resolving any minor issues. We hope to host you again soon!

Heavenly!

Reviewed by Cathy H. on 2021-09-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Had the opportunity to stay in Key West for 33 days. It was perfection! The house was exactly what I wanted. A Key West classic with charm. Perfectly imperfect in every way, even when an iguana fell out of the tree into the pool inches from my floaty...twice. It's Key West after all, I just laughed and was grateful it didn't land on me. Angela was great and helped with any little thing. Loved loved loved my stay.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Thank you for your fantastic review! We’re so glad you found Heavenly Hideaway to be exactly what you wanted for your stay in Key West. It sounds like you embraced the charm of Key West—even when the iguanas made a splash! We loved hearing about your 33 days of perfection and can’t wait to have you back.

Perfect Hideaway

Reviewed by Bob T. on 2021-04-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This property is in a terrific old town location, close to everything, yet in a quiet location. A very well maintained home. Angela Hart, of Preferred Properties, is the best representative my wife & I have dealt with in our 15 years of renting properties in Key West. Angela went out of her way to make sure things at the property were perfect.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Bob, Thank you for your wonderful review! We’re delighted that you enjoyed Heavenly Hideaway's great location and well-maintained charm. We’re especially happy to hear that Angela went above and beyond to make sure your stay was perfect. We look forward to welcoming you back to Key West!

Amazing stay! Great location

Reviewed by Matthew T. on 2021-01-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great property, very responsive staff. Heated pool was perfect.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Matthew, Thank you for your fantastic review! We’re thrilled to hear that you loved the location, the property, and the heated pool. It’s great to know our team was responsive and helpful during your stay. We look forward to hosting you again!

heavenly hideaway

Reviewed by Abigail C. on 2020-02-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
this is an appropriate name for this cottage located in a central but very quiet part of Old Town. We love this location on a quiet lane but only several blocks from restaurants, the harbor, and all that makes Key West fun. The staff at Preferred Properties is terrific and make every effort to be helpful. This was our second year in this lovely house.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Hi Abigail, Thank you for your lovely review! We’re thrilled that you enjoyed the peaceful and central location of Heavenly Hideaway and had a wonderful experience with our staff. It’s great to hear that this was your second stay, and we can’t wait to welcome you back for another visit!

Media

Heavenly Hideaway Monthly 3BD 2.5BA Private Pool

Unit Code: 917A

Heavenly Hideaway

This beautifully unique private pool home is a hidden treasure. Heavenly Hideaway is located across the street from our Historic Key West Cemetery and is in a quiet neighborhood. A plus to this home is it comes with parking for 2 small cars or large truck.
HEAVENLY HIDEAWAY! Welcome to our Heavenly Hideaway, a serene oasis nestled in the heart of Key West. This enchanting 3-bedroom, 1.5-bath property comfortably sleeps 6, offering a divine blend of comfort and convenience. The home features a private, heated pool, a tranquil haven where you can unwind under the Florida sun. Inside, the decor radiates a warm, family-friendly ambiance, creating a cozy and inviting atmosphere that transforms our property into a sanctuary, your home away from home. The spacious layout ensures you'll never feel crowded, even with a full house. Our covered porch, encircled by palm trees and caressed by warm breezes, is the perfect spot for heavenly meals in a fully-equipped kitchen with provided cookware. Despite its serene setting on a quiet, one-way street lined with the historic Key West Cemetery, the Heavenly Hideaway is just a half-mile from the vibrant energy of Duval Street and the Historic Seaport. Enjoy the best of both worlds as you explore the lively bars, restaurants, and shops, then retreat to the peaceful seclusion of your celestial vacation home. The Heavenly Hideaway includes a range of amenities to ensure a comfortable stay, including free WiFi, linens, and a dedicated parking spot. Please note that a minimum stay of 29 days is required, and pets may be considered upon request. The neighborhood is quiet and respectful, offering a peaceful retreat from the hustle and bustle of Duval Street. And as for the cemetery across the street? Let's say our neighbors are the quietest you'll ever meet. Our guests often comment on our responsive and helpful staff, who are always ready to ensure your stay is perfect. Experience the charm of Key West from the comfort and convenience of our Heavenly Hideaway. We look forward to welcoming you to your celestial home away from home. Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. Monthly Rental Only (This property must be rented for 29 or more days by city ordinance)
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Age 24 and under.
DatesPrice
03/01/2026 - 05/31/2026$336 /nt
03/01/2026 - 05/31/2026$10,075 /month
06/01/2026 - 08/31/2026$246 /nt
09/01/2026 - 11/30/2026$246 /nt
09/01/2026 - 11/30/2026$266 /nt
09/01/2026 - 11/30/2026$7,892 /month
09/01/2026 - 11/30/2026$7,915 /month
12/01/2026 - 02/28/2027$416 /nt
12/01/2026 - 02/28/2027$508 /nt
12/01/2026 - 02/28/2027$12,558 /month
12/01/2026 - 02/28/2027$12,567 /month
03/01/2027 - 05/31/2027$353 /nt
03/01/2027 - 05/31/2027$508 /nt
4.8333
(12 Review)

Year 3 at the Heavenly Hideaway

February 2025
, North Falmouth, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My family and I spent the month of February at the Heavenly Hideaway for the third year in a row and it was truly a perfect experience. The location is unbeatable – we were able to walk everywhere, from grocery stores to fantastic bars and restaurants.

The house itself is charming and well-maintained, with all the amenities we needed for a comfortable stay. The highlight for our family was the pool – my grandson absolutely loved swimming every day, and it became a special part of our routine.

If you’re looking for a peaceful yet central spot to enjoy Key West, this is it. We can’t wait to return next year!

holiday cottage

March 2024
, New Orleans, LA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

wonderful

Manager's Response

Hi,

Thank you for your wonderful review! We’re thrilled that you enjoyed your stay at Heavenly Hideaway and found everything to be perfect. We hope to welcome you back again soon!

holiday cottage

March 2024
, New Orleans, LA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

wonderful

Manager's Response

Hi,

Thank you for your wonderful review! We’re thrilled that you enjoyed your stay at Heavenly Hideaway and found everything to be perfect. We hope to welcome you back again soon!

Quite nice

January 2024
, Traverse City, MI United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
4

We loved the privacy combined with a great location. The porch could use a little trimming so as to be able to interact with people strolling by.

Manager's Response

Hi,

Thank you for your kind review and for sharing your feedback about the porch. We're happy to hear that you loved the privacy and the location. We’ll definitely take your suggestion about trimming the porch foliage into consideration to enhance the guest experience. We hope to welcome you back again soon!

Quite nice

January 2024
, Traverse City, MI United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
4

We loved the privacy combined with a great location. The porch could use a little trimming so as to be able to interact with people strolling by.

Heavenly indeed!

February 2023

Overall
5

We thoroughly enjoyed our month at Heavenly Hideaway. Our family of 5 adults and 1 infant enjoyed many meals on the covered porch after cooking on the provided grill. We never felt crowded as there are multiple areas to gather There were a couple of minor "issues" that we needed to call the property manager for. I was happily surprised by how quickly and efficiently they took care of everything!

The name says it all!

February 2023
, North Falmouth, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We couldn't be happier with our stay at Heavenly Hideaway. Our family of 5 were very comfortable and never felt as though we were crowded at all. We enjoyed our meals on the covered porch surrounded by palm trees and warm breezes. Who could ask for more?

Manager's Response

Hi Kathryn,

Thank you for your fantastic review! We’re so happy to hear that your family had a wonderful time and enjoyed all the spacious gathering areas at Heavenly Hideaway. It’s also great to know our team was quick and efficient in resolving any minor issues. We hope to host you again soon!

Heavenly!

August 2021
, Snohomish, WA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Had the opportunity to stay in Key West for 33 days. It was perfection! The house was exactly what I wanted. A Key West classic with charm. Perfectly imperfect in every way, even when an iguana fell out of the tree into the pool inches from my floaty...twice. It's Key West after all, I just laughed and was grateful it didn't land on me. Angela was great and helped with any little thing. Loved loved loved my stay.

Manager's Response

Thank you for your fantastic review! We’re so glad you found Heavenly Hideaway to be exactly what you wanted for your stay in Key West. It sounds like you embraced the charm of Key West—even when the iguanas made a splash! We loved hearing about your 33 days of perfection and can’t wait to have you back.

Perfect Hideaway

February 2021
, Berlin, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This property is in a terrific old town location, close to everything, yet in a quiet location. A very well maintained home. Angela Hart, of Preferred Properties, is the best representative my wife & I have dealt with in our 15 years of renting properties in Key West. Angela went out of her way to make sure things at the property were perfect.

Manager's Response

Hi Bob,

Thank you for your wonderful review! We’re delighted that you enjoyed Heavenly Hideaway's great location and well-maintained charm. We’re especially happy to hear that Angela went above and beyond to make sure your stay was perfect. We look forward to welcoming you back to Key West!

Amazing stay! Great location

November 2020
, Saint Louis, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great property, very responsive staff. Heated pool was perfect.

Manager's Response

Hi Matthew,

Thank you for your fantastic review! We’re thrilled to hear that you loved the location, the property, and the heated pool. It’s great to know our team was responsive and helpful during your stay. We look forward to hosting you again!

heavenly hideaway

January 2020
, New York, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

this is an appropriate name for this cottage located in a central but very quiet part of Old Town. We love this location on a quiet lane but only several blocks from restaurants, the harbor, and all that makes Key West fun. The staff at Preferred Properties is terrific and make every effort to be helpful. This was our second year in this lovely house.

heavenly hideaway

January 2020
, New York, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

this is an appropriate name for this cottage located in a central but very quiet part of Old Town. We love this location on a quiet lane but only several blocks from restaurants, the harbor, and all that makes Key West fun. The staff at Preferred Properties is terrific and make every effort to be helpful. This was our second year in this lovely house.

Manager's Response

Hi Abigail,

Thank you for your lovely review! We’re thrilled that you enjoyed the peaceful and central location of Heavenly Hideaway and had a wonderful experience with our staff. It’s great to hear that this was your second stay, and we can’t wait to welcome you back for another visit!

Leave a Review
3 Bed
1.5 Baths
Sleeps 6

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Foundry 7

Historic Elegance in Key West’s Truman Annex neighborhood of Old Town. A stunning 3-story townhome steps from Duval & Beach

Location

101 Front Street Unit: #7
33040 Key West , FL
United States
24° 33' 18.7632" N, 81° 48' 23.94" W
Florida US

Foundry 7

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Key West

Reviewed by Al B. on 2025-11-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
excellent residence and location

Absolutely beautiful property and location

Reviewed by Sean C. on 2025-09-24
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
My self, my wife and 2 friends stayed here for a week in September. The property is in pristine condition, with everything you need for a longer stay or just a few days away. The property could not be in a better location. A five minute stroll to Duval st and passing several historical location on the way. Look up the area and you will see it could be located in a better place.
The office staff are very friendly and so helpful, I know because I contacted them with all my dumb questions a few times. They reply immediately and are so helpful. 5 stars all around for staff location and the property. Thank you so much. We will be back soon.

Best Location and Value

Reviewed by Chris A. on 2025-07-28
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Foundry 7 has the best location in Key West. Peaceful neighborhood and a very short walk to Duval St. Our family's first time to stay at Tuman Annex and won't be our last. I cannot recommend this place enough.

Great Place!

Reviewed by Vincent D. on 2025-06-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was our first time staying at the Foundry but not in Truman Annex and it was very delightful. It was within easy walking distance of everything on that side of the island and we took advantage and walking around. The only thing that was different from every other time that we visited is that there were no spices and condiments. Ww usually buy some food to cook but didn't want to buy anything just to have to throw it away so that was disappointing, but other than that we had a wonderful time, great and relaxing bed, comfortable couch and beautiful scenery!

We were able to get into the house 3 hrs early and the management team was completely thorough and helpful from the initial booking until we landed.

The walk to Harpoon Harry's, Two Friends, The glass bottom boat at Sunset Pier, and even the stores and shops were easy to get to and get back to the house.

Nice Place, Great Location!

Reviewed by Lonny P. on 2025-06-29
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Right where we wanted to stay in old town but a very quiet street/area. Very clean and comfortable.

First time to Key West was a great experience.

Reviewed by Loren W. on 2025-01-03
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I was lucky to find Foundry 7 to stay my first time in Key West. The condo was very clean and quiet at night and just a short walk to Duval Street. The condo met all our expectations and was a great place to relax after a busy day of sight seeing. We will definitely stay here again if and when we get a chance to visit Key West again.

Week in Key West

Reviewed by Unknown on 2024-10-13
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The townhouse was clean and very convenient to Duval St, Mallory Square and other local attractions. Perfect size for 2 adult couples with two master suites with bathrooms.

Exceptional Service & Amazing Stay! Highly recommend!

Reviewed by Elizabeth L. on 2024-08-28
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Preferred Properties Management provided top notch service during my family's 10-day stay at Foundry 7. Not only did they answer all of my questions and requests almost immediately, but they went above and beyond in terms of customer service. Truly a 5-star organization! Our rental home was very clean, spacious, and perfectly located! Not only are you are short bike ride away from Fort Zachary Taylor State Park and beach, but you are just steps away from Duval Street, but WITHOUT any street noise. My family and I will hold great memories of our stay there for a lifetime.

A Comfy Find

Reviewed by Dawn K. on 2024-08-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We enjoyed our stay at the Foundry. It was a great location and a very comfortable condo. The realty company couldn’t have been more accommodating. They were on top of everything we needed. I wish the shared pool was a little closer and larger, and I would have liked to have had a more open balcony off of the second floor bedroom. I had to stand to see the view.

Inviting and cozy respite plus location, location, location!!!

Reviewed by Cynthia K. on 2024-07-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I couldn’t think of anything this property didn’t have. My granddaughters HS grad trip was made complete in this beautiful 3 story charmer. I felt completely at home. My granddaughter fell in love with the 3rd level king bed en suite. Gpa and I had the 2nd floor king bed en suite complete with w/d and balcony. The 1st floor was had everything for cooking, relaxing, watching TV as well as a courtyard and porch to drink coffee or cocktails on. We loved the location, in this gorgeous gated community. We literally walked to everything. Steps away from Mallory Square for sunsets and fresh seafood or walk to Southernmost Point and 0 mile marker. Duval St and all the shops, restaurants and bars were steps away too. It even came with a designated parking space and community pool. Our fav places to eat were A&B Lobsterhouse, Onlywood Pizza. Sarabeth’s and Azure had delectable brunch. We even watched a newly released movie at the Tropic Cinema while enjoying popcorn, beer and wine. It’s within a 2 block walk. I would gladly return to this immaculate and well appointed property, suitable and safe enough for a girl trip or romantic enough for a honeymoon. My only regret was we didn’t book a 2nd week. 5+ stars.

Foundry 7

Reviewed by Cynthia P. on 2024-06-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The rental was very nice. The unit was clean and updated. It had all the amenities that we needed. The pool was a disappointment because it was small (cap. 7) and was split between two developments.

Lovely property, lovely location

Reviewed by Unknown on 2023-10-17
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
From the ease of booking, to the communication from the rental company, it was all great. Once arriving at the property, everything was as nice as the pictures show.
A great location, clean and quiet, but near to everything, allowing us to walk to Duval, Mallory square etc.

Truman Annex great location

Reviewed by Unknown on 2023-06-23
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Close to all the activities but in a beautiful gated community. The townhouse was clean and comfortable. The property managers were attentive to our requests and questions. Walking distance to shopping, restaurants, beaches and nightlife!

Fabulous!

Reviewed by Kristen M. on 2022-12-26
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house was perfect and was fully equipped. Great location. We were able to walk to The beach and most attractions. Property Management staff was very helpful and attentive! Highly recommend.

Excellent location

Reviewed by Laura S. on 2022-11-27
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This townhome in the Truman Annex is located in a perfect spot for access to all Key West has to offer. The AC went out on our 2nd day but Preferred Properties was excellent in getting someone there to resolve the issue. Foundry 7 could use some updates to the furniture/ carpeting etc. but this didn’t keep us from enjoying our stay.

Best Vacay House Ever!

Reviewed by Amy B. on 2022-10-25
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We absolutely loved this house! The location was absolutely perfect, house layout was perfect for two couples, beds were very comfortable, house was clean. We’d definitely rent this place again in the future.

September 2022

Reviewed by Mary Beth N. on 2022-10-18
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our stay was to occur when Hurricane Ian was to hit Florida. We decided not to risk our safety and headed home. However we did manage a day trip to Key West and took a look at the property. It was a beautiful place and centrally located to shopping and several tourist sites, all within walking distance. The management company was a pleasure to work with keeping in contact almost daily up to the start date. I look forward to staying here in the future and experiencing all that Key West has to offer.

Vacation 2022

Reviewed by Penny F. on 2022-10-11
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Vacation rental was as described nice place to stay close to everything!!!
Property management was helpful! Key west is awesome we took 2 fishing trips on the salty Goat caught lots of fish was great for dinner sunset cruise on the flurry lots of fun!!’

Great location!

Reviewed by Michelle C. on 2022-07-26
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We loved staying in Truman Annex. I've been visiting Key West for 20+ years and this is my first time in this area of town. I loved the location and the property and enjoyed having a full kitchen and beautiful patio. The property was clean and very well maintained. I will definitely return.

Wonderful Spot for Key West Get Away

Reviewed by Mike and Helen C. on 2022-07-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Foundry 7 was the perfect spot to celebrate our 40th wedding anniversary in Key West. We enjoyed our honeymoon there and decided to return after 40 years and we were joined by our son and his wife. The management group responded immediately to have two bicycles waiting for us and also to fix a window shade that would not open.
Everything was so very clean and bright inside. The location made it perfect for riding bikes or walking to town, to the State Park beach, to the Southernmost Point, and to all the wonderful restaurants. What an ideal location!

Foundry 7

Reviewed by Unknown on 2021-09-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Loved the location of the Foundry. The space was large enough for our family of four. We were happy with the townhouse. The only problem with this rental is the size of the pool-way to small. We never swam in it-it was always full. The only reason I would not stay here again is because of the size of the pool-really like an oversized hot tub.

Amazing time and place!

Reviewed by Debra T. on 2021-09-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
It was the perfect getaway for our honeymoon. So close to everything and yet so peaceful at night. It had everything we needed and the neighborhood was clean, private, and convenient to everything we wanted to do. The property management group was so helpful and quick to reply to any of my questions! It made our trip that much more memorable and we will return for sure!

Wonderful location

Reviewed by Rhianna F. on 2021-08-10
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
From the time I booked there was constant communication between the property manager and myself. Once we arrived the property had everything we needed and the location was perfect. The property was extremely clean and the manual answered all questions. We will definitely be back.

Great Condo in a Good Location

Reviewed by Robert C. on 2021-06-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Condo was as described, clean and functional; everything worked as described.

Foundry 7

Reviewed by Karen C. on 2021-06-12
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Very nice townhouse. Great location. Beautiful weather! Gorgeous sunsets! Friendly people! Most places (no masks) felt like “normal times”. Friendly people! Quiet place! Close to Duval St. It was wonderful. Wish we stayed longer.

The Foundry

Reviewed by Debra P. on 2021-05-24
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
AWESOME

An island of civility in Key west ��

Reviewed by Craig V. on 2021-04-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Easter/Spring Break vacation with my family could not have gone better. Love the location of these units. Close to Duval and Mallory Square and yet peaceful and quiet at night. Should we choose to return Key West, this will be where we stay.

Great Place

Reviewed by Bob R. on 2021-03-06
Recommend to Others
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Location
Cleanliness
Services from rental manager
Overall satisfaction
Terrific

Great location!

Reviewed by Unknown on 2020-10-09
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The location was great. The accommodations were clean and both bedrooms had a king size bed which is great for two couples traveling together. We had a TV issues and was fixed by the next morning, very responsive. The people we dealt with for registration, etc. were very nice and accommodating.

Good Visit to Key West

Reviewed by Unknown on 2019-12-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Our experience at Foundry 7 was good. Comms with Preferred Properties in advance of the visit were good, I was aware of everything in advance. Angela from the office reached out to me a few days prior to the visit, and during the visit, as needed. The accomodations at Foundry 7 were nice. There were a few relatively minor cleanliness issues--the cleaning crew did not do a great job, we found crumbs on the kitchen counter, and the bath towels smelled like mildew. Ceiling fan blades and bathroom exhaust fan covers hadn't been cleaned in months.
The location was choice. A short walk to Truman Waterfront Park, a short walk to Duval St and Whitehead St, many attractions walking distance. Reserved parking behind the building. A nice pool area which we didn't use.

Great location

Reviewed by Julie G. on 2019-12-01
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Would stay here again solely because of quiet neighborhood but walkable to everything. Beautiful neighborhood and pool. Decor was dated and somewhat worn but everything needed was there. Would have loved a mattress pad on the third floor bed and instructions on keys needed for opening bathroom and pool and Truman gates that shut in the evening. Fortunately everyone friendly in the neighborhood and by day 3 we had figured it out.

Great Rental

Reviewed by Unknown on 2019-07-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Great rental with great service.
Manager response on 2019-08-23 - Response from Preferred Properties Management LLC
Thank you for the great ratings and great review. :-)

Retirement party

Reviewed by Alvin H. on 2017-12-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We had a great time watching cruise ships come and go and then able to walk every where and enjoying all of the restaurants and the location we never had to use the car once we got to our property. We will continue to use preferred property when we look for a place in Key West Fl.
Manager response on 2019-05-28 - Response from Preferred Properties Management LLC
Thank you for your nice review. We are glad that you recognized how nice it is to be so close to so many of the Key West attractions and restaurants. It's a huge asset of the home.

Wonderfull stay in Key West

Reviewed by Jim F. on 2017-11-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This property was great, a good location close to Duval Street yet quiet. Condo was clean and well stocked we would rent this property again when we return for another visit
Manager response on 2019-05-28 - Response from Preferred Properties Management LLC
Thanks for your review. The Foundry in many ways is a nice secret, to be able to escape the hustle and bustle of Duval Street yet also be so close when you are ready to jump into the fun again! We look forward to your next trip!

Foundry 7 - Historic Luxury in the Heart of Key West-Great 2 Bedroom/2 Bath

Unit Code: 101F-7

Foundry 7

Historic Elegance in Key West’s Truman Annex neighborhood of Old Town. A stunning 3-story townhome steps from Duval & Beach
Welcome to Foundry 7 – A Rare Gem in Key West’s Prestigious Truman Annex! Step into paradise at Foundry 7, a spectacular 3-story townhome set in one of Key West’s most sought-after gated neighborhoods—just steps from the iconic Truman White House, world-famous Duval Street, and the sparkling waterfront. Once the site of historic Fort Zachary, this exclusive retreat offers a seamless blend of old-world charm and high-end modern luxury. Enter through your private tropical courtyard, perfect for alfresco dining with a built-in BBQ and lush landscaping. Inside, dramatic vaulted ceilings, designer furnishings, and an open-concept layout create a bright, breezy space made for relaxation and entertaining. The fully equipped kitchen has everything you need—from a blender for beachy cocktails to a drip-coffee maker for your morning fix. Upstairs, the master suite is a serene sanctuary with a private balcony for stargazing or sipping sunrise coffee. A guest suite with its own bathroom sits on the third floor, offering privacy and comfort for friends or family. Plus, enjoy the convenience of an in-unit washer/dryer, central A/C, and high-speed WiFi throughout. Take a refreshing dip in the heated community pool, then stroll or bike to beaches, art galleries, buzzing bars, and world-class dining. With one dedicated parking spot, premium linens provided, and everything at your fingertips, all that’s left to do is check in and unwind. Foundry 7 is not just a vacation rental – it’s your private escape to the best of Key West. **Monthly Rental Only starting January 1, 2026** Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
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Age 24 and under.
DatesPrice
03/01/2026 - 05/31/2026$5,725 /wk
03/01/2026 - 05/31/2026$6,130 /wk
03/01/2026 - 05/31/2026$6,141 /month
03/01/2026 - 05/31/2026$6,579 /month
06/01/2026 - 08/31/2026$5,777 /wk
06/01/2026 - 08/31/2026$6,351 /wk
06/01/2026 - 08/31/2026$6,196 /month
06/01/2026 - 08/31/2026$6,824 /month
09/01/2026 - 11/30/2026$5,738 /wk
09/01/2026 - 11/30/2026$9,433 /wk
09/01/2026 - 11/30/2026$6,126 /month
09/01/2026 - 11/30/2026$9,950 /month
12/01/2026 - 02/28/2027$7,966 /wk
12/01/2026 - 02/28/2027$9,838 /wk
12/01/2026 - 02/28/2027$8,484 /month
12/01/2026 - 02/28/2027$10,376 /month
03/01/2027 - 05/31/2027$7,596 /wk
03/01/2027 - 05/31/2027$10,662 /wk
03/01/2027 - 05/31/2027$8,121 /month
03/01/2027 - 05/31/2027$11,384 /month
4.9429
(35 Review)

Key West

October 2025
, Brookfield, WI Unknown

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

excellent residence and location

Absolutely beautiful property and location

September 2025
, Newcastle, OK US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

My self, my wife and 2 friends stayed here for a week in September. The property is in pristine condition, with everything you need for a longer stay or just a few days away. The property could not be in a better location. A five minute stroll to Duval st and passing several historical location on the way. Look up the area and you will see it could be located in a better place.
The office staff are very friendly and so helpful, I know because I contacted them with all my dumb questions a few times. They reply immediately and are so helpful. 5 stars all around for staff location and the property. Thank you so much. We will be back soon.

Best Location and Value

July 2025
, Dallas, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Foundry 7 has the best location in Key West. Peaceful neighborhood and a very short walk to Duval St. Our family's first time to stay at Tuman Annex and won't be our last. I cannot recommend this place enough.

Nice Place, Great Location!

June 2025
, Jacksonville, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Right where we wanted to stay in old town but a very quiet street/area. Very clean and comfortable.

Great Place!

June 2025
, St Peters, MO US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This was our first time staying at the Foundry but not in Truman Annex and it was very delightful. It was within easy walking distance of everything on that side of the island and we took advantage and walking around. The only thing that was different from every other time that we visited is that there were no spices and condiments. Ww usually buy some food to cook but didn't want to buy anything just to have to throw it away so that was disappointing, but other than that we had a wonderful time, great and relaxing bed, comfortable couch and beautiful scenery!

We were able to get into the house 3 hrs early and the management team was completely thorough and helpful from the initial booking until we landed.

The walk to Harpoon Harry's, Two Friends, The glass bottom boat at Sunset Pier, and even the stores and shops were easy to get to and get back to the house.

First time to Key West was a great experience.

December 2024
, Noblesville, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I was lucky to find Foundry 7 to stay my first time in Key West. The condo was very clean and quiet at night and just a short walk to Duval Street. The condo met all our expectations and was a great place to relax after a busy day of sight seeing. We will definitely stay here again if and when we get a chance to visit Key West again.

Week in Key West

September 2024
, Wilmington, DE United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

The townhouse was clean and very convenient to Duval St, Mallory Square and other local attractions. Perfect size for 2 adult couples with two master suites with bathrooms.

Exceptional Service & Amazing Stay! Highly recommend!

July 2024
, Prevessin-Moens, A01 France

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Preferred Properties Management provided top notch service during my family's 10-day stay at Foundry 7. Not only did they answer all of my questions and requests almost immediately, but they went above and beyond in terms of customer service. Truly a 5-star organization! Our rental home was very clean, spacious, and perfectly located! Not only are you are short bike ride away from Fort Zachary Taylor State Park and beach, but you are just steps away from Duval Street, but WITHOUT any street noise. My family and I will hold great memories of our stay there for a lifetime.

Inviting and cozy respite plus location, location, location!!!

July 2024
, MOUNT VERNON, TX US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I couldn’t think of anything this property didn’t have. My granddaughters HS grad trip was made complete in this beautiful 3 story charmer. I felt completely at home. My granddaughter fell in love with the 3rd level king bed en suite. Gpa and I had the 2nd floor king bed en suite complete with w/d and balcony. The 1st floor was had everything for cooking, relaxing, watching TV as well as a courtyard and porch to drink coffee or cocktails on. We loved the location, in this gorgeous gated community. We literally walked to everything. Steps away from Mallory Square for sunsets and fresh seafood or walk to Southernmost Point and 0 mile marker. Duval St and all the shops, restaurants and bars were steps away too. It even came with a designated parking space and community pool. Our fav places to eat were A&B Lobsterhouse, Onlywood Pizza. Sarabeth’s and Azure had delectable brunch. We even watched a newly released movie at the Tropic Cinema while enjoying popcorn, beer and wine. It’s within a 2 block walk. I would gladly return to this immaculate and well appointed property, suitable and safe enough for a girl trip or romantic enough for a honeymoon. My only regret was we didn’t book a 2nd week. 5+ stars.

A Comfy Find

March 2024
, Akron, OH United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We enjoyed our stay at the Foundry. It was a great location and a very comfortable condo. The realty company couldn’t have been more accommodating. They were on top of everything we needed. I wish the shared pool was a little closer and larger, and I would have liked to have had a more open balcony off of the second floor bedroom. I had to stand to see the view.

Lovely property, lovely location

October 2023
, Windlesham, GB

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

From the ease of booking, to the communication from the rental company, it was all great. Once arriving at the property, everything was as nice as the pictures show.
A great location, clean and quiet, but near to everything, allowing us to walk to Duval, Mallory square etc.

Truman Annex great location

May 2023
, Naperville, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Close to all the activities but in a beautiful gated community. The townhouse was clean and comfortable. The property managers were attentive to our requests and questions. Walking distance to shopping, restaurants, beaches and nightlife!

Fabulous!

November 2022
, Stevensville, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was perfect and was fully equipped. Great location. We were able to walk to The beach and most attractions. Property Management staff was very helpful and attentive! Highly recommend.

Excellent location

November 2022
, Orland Park, IL United States

Overall
5
Services from rental manager
5
Cleanliness
3
Location
5
Property condition
3

This townhome in the Truman Annex is located in a perfect spot for access to all Key West has to offer. The AC went out on our 2nd day but Preferred Properties was excellent in getting someone there to resolve the issue. Foundry 7 could use some updates to the furniture/ carpeting etc. but this didn’t keep us from enjoying our stay.

Best Vacay House Ever!

October 2022
, Greenwich, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We absolutely loved this house! The location was absolutely perfect, house layout was perfect for two couples, beds were very comfortable, house was clean. We’d definitely rent this place again in the future.

Vacation 2022

October 2022
, Church Road, VA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Vacation rental was as described nice place to stay close to everything!!!
Property management was helpful! Key west is awesome we took 2 fishing trips on the salty Goat caught lots of fish was great for dinner sunset cruise on the flurry lots of fun!!’

September 2022

September 2022
, Aston, PA United States

Overall
4
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4

Our stay was to occur when Hurricane Ian was to hit Florida. We decided not to risk our safety and headed home. However we did manage a day trip to Key West and took a look at the property. It was a beautiful place and centrally located to shopping and several tourist sites, all within walking distance. The management company was a pleasure to work with keeping in contact almost daily up to the start date. I look forward to staying here in the future and experiencing all that Key West has to offer.

Great location!

July 2022
, Southlake, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We loved staying in Truman Annex. I've been visiting Key West for 20+ years and this is my first time in this area of town. I loved the location and the property and enjoyed having a full kitchen and beautiful patio. The property was clean and very well maintained. I will definitely return.

Wonderful Spot for Key West Get Away

June 2022
, Danville, IN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Foundry 7 was the perfect spot to celebrate our 40th wedding anniversary in Key West. We enjoyed our honeymoon there and decided to return after 40 years and we were joined by our son and his wife. The management group responded immediately to have two bicycles waiting for us and also to fix a window shade that would not open.
Everything was so very clean and bright inside. The location made it perfect for riding bikes or walking to town, to the State Park beach, to the Southernmost Point, and to all the wonderful restaurants. What an ideal location!

Foundry No. 7

November 2021

Overall
5

Thoroughly enjoyed this rental unit. Entire process was simple from arrival to leaving. Home is beautifully decorated just as it appears in the photos. Beds are very comfortable. It is easy access to Duval Street, Mallory Square and Fort Zachary State Park. We would definitely stay here again if returning to Key West.

key west

September 2021

Overall
5

nice stay

Amazing time and place!

August 2021
, Marietta, SC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It was the perfect getaway for our honeymoon. So close to everything and yet so peaceful at night. It had everything we needed and the neighborhood was clean, private, and convenient to everything we wanted to do. The property management group was so helpful and quick to reply to any of my questions! It made our trip that much more memorable and we will return for sure!

Amazing time and place!

August 2021
, Marietta , South Carolina United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

It was the perfect getaway for our honeymoon. So close to everything and yet so peaceful at night. It had everything we needed and the neighborhood was clean, private, and convenient to everything we wanted to do. The property management group was so helpful and quick to reply to any of my questions! It made our trip that much more memorable and we will return for sure!

Wonderful location

July 2021
, North Royalton, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

From the time I booked there was constant communication between the property manager and myself. Once we arrived the property had everything we needed and the location was perfect. The property was extremely clean and the manual answered all questions. We will definitely be back.

Summer Vacation

July 2021

Overall
5

Great location, quaint neighborhood, walk to everything!

Fantastic! Great location. Beautiful home.

July 2021

Overall
5

Everything was smooth. No problems.

Foundry 7

June 2021
, West Richland, WA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
5

Very nice townhouse. Great location. Beautiful weather! Gorgeous sunsets! Friendly people! Most places (no masks) felt like “normal times”. Friendly people! Quiet place! Close to Duval St. It was wonderful. Wish we stayed longer.

Great Condo in a Good Location

May 2021
, PENROSE, CO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Condo was as described, clean and functional; everything worked as described.

Awesome vacation

May 2021

Overall
5

This property was fantastic!!! Definitely hope to return again soon!! So convenient, any question was answered almost instantly!!!! It was the easiest reservation, check in, stay, & check out ive ever experienced!!! Can’t say enough positive things!!!

An island of civility in Key west ��

March 2021
, Brecksville, OH Unknown

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
3

Easter/Spring Break vacation with my family could not have gone better. Love the location of these units. Close to Duval and Mallory Square and yet peaceful and quiet at night. Should we choose to return Key West, this will be where we stay.

Great Place

February 2021
, Baltimore, MD United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Terrific

Great location!

September 2020
, Suwanee, GA US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The location was great. The accommodations were clean and both bedrooms had a king size bed which is great for two couples traveling together. We had a TV issues and was fixed by the next morning, very responsive. The people we dealt with for registration, etc. were very nice and accommodating.

Great location

November 2019
, Huron, OH US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Would stay here again solely because of quiet neighborhood but walkable to everything. Beautiful neighborhood and pool. Decor was dated and somewhat worn but everything needed was there. Would have loved a mattress pad on the third floor bed and instructions on keys needed for opening bathroom and pool and Truman gates that shut in the evening. Fortunately everyone friendly in the neighborhood and by day 3 we had figured it out.

Great Rental

June 2019
, Aiken, SC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Great rental with great service.

Manager's Response

Thank you for the great ratings and great review. :-)

Wonderfull stay in Key West

October 2017
, Gardnerville, NV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This property was great, a good location close to Duval Street yet quiet. Condo was clean and well stocked we would rent this property again when we return for another visit

Manager's Response

Thanks for your review. The Foundry in many ways is a nice secret, to be able to escape the hustle and bustle of Duval Street yet also be so close when you are ready to jump into the fun again! We look forward to your next trip!

Leave a Review
2 Bed
2.5 Baths
Sleeps 5

Search Availability

Tropical Jewel

Colorful and Quirky 2BD/2BA Key West Home near Historic Seaport - Monthly Rental

Location

320 Elizabeth Street
33040 Key West , FL
United States
24° 33' 32.004" N, 81° 48' 6.192" W
Florida US

Tropical Jewel

Request More Information

Awesome month at Tropical Jewel

Reviewed by Ronald M. on 2026-02-05
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This was really an awesome location, surprisingly quiet, given its location, close to the action in Key West, and extremely well kept. Really had a fabulous experience, well stocked, and perfect size for our needs. The management company was very responsive to needs, and our day was wonderful.

Tropical Jewel was better than we expected.

Reviewed by Ted S. on 2025-12-16
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
We loved Tropical Jewel. Private pool was awesome. Fully furnished house and kitchen.Great walkable location.

Easy Living in Key West

Reviewed by Vincent C. on 2025-04-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Third time renting Tropical Jewel. Great location and great pool. Angela from Preferred Properties was a pleasure to deal with. Any questions we had she immediately answered.

Great stay at Tropical Jewel!

Reviewed by Ronald M. on 2025-02-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
House was perfect! Great backyard oool, quiet street, perfect location!

Great Location and Great Customer Service

Reviewed by Brandie R. on 2025-01-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Property was even better than described. Great convenient location to EVERYTHING! Management company responded with any questions to any of our needs. I would definitely stay here again and recommend anyone to stay at this property.
Pool and Covered Porch was a great asset!!

Beautiful Oasis

Reviewed by Karen F. on 2025-01-08
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
I can’t express how much I love this house.
We stayed for a month in October and really really didn’t want to leave.
As our driver arrived I touched the house and said ‘ we ll be back’ it may sound bonkers !

The booking process was simple and Angela at PP was a dream to deal with, keeping us up to date with any changes etc
Communication was fantastic

Anyway the arrival was simple and the electronic door locks meant no one needed to carry keys which was a bonus.
The accommodation was spotless and spacious. The kitchen was well equipped and organised and the overall decor was sunny and tropical.
Having tvs in each bedroom meant we could have some freedom from watching same old programmes. Also the highlight for me was watching a programme called ‘Midsommer Murders’ whilst being outside in the pool. The outdoor tv was awesome!

Both bedrooms had a bathroom / shower each. We didn’t use the mezzanine bedroom (only to store our luggage). However kids would love this area.

My favourite area was the pool deck and outdoor cocktail kitchen!
The pool was heated and larger than i expected which is unusual in KW.
It is private and is surrounded by lush foliage which brings nature into the garden which was wonderful.
I wish i could share a couple of pics but there doesn’t seem to be an option.

The location was perfect , close to the Seaport and Duval but quiet. Also close to Faustos who told us we could wheel our shopping home in the trolley as long as we returned it!! That’s how close.

Finally i d like to say it has the perfect balance of luxury and comfort and please can we come back.


Hidden gem

Reviewed by Kay A. on 2024-06-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
Convenient location in a quiet neighborhood, but close to the harbor and restaurants. Private backyard with a beautiful pool. Rental company is very responsive. Only downside is the guest bedroom is small.

Lovely Home

Reviewed by Unknown on 2024-03-15
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This sweet house is in a great location - all of our favorite places within walking or biking distance. Neighborhood quiet, except for the roosters of course! We love working with the staff at Preferred Properties - Angela is amazing.
Manager response on 2024-03-21 - Response from Preferred Properties Management LLC
Thank you for the kind words and we look forward to hosting you again in the future.

Great Location and Great House

Reviewed by Nicole R. on 2023-02-14
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
The house was in the perfect location, perfectly clean with a wonderful pool. We loved our stay here, and always love working with Preferred Properties!

November 2020

Reviewed by Diane M. on 2020-12-02
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This is my second time renting the Tropical Jewel and it is was again an absolutely a fabulous rental property. Every morning I made a pot of coffee and sat in the yellow lounge and felt the sweet island breezes and the sounds of Key West. The house is 2 blocks off Duval - great for taking in the sights. A quaint little cottage and the pool is wonderful. The property managers (Angela, Phil, and Meghan) were there at a moments notice to answer questions or take care of any problems that might arise. I would highly recommend this property!!
Manager response on 2020-12-02 - Response from Preferred Properties Management LLC
Diane, You made our jobs easy. Your easy going attitude and love of the Key West lifestyle, combined with an ideal property, ensured that we would excel at providing this wonderful experience to you AGAIN. We also just really enjoy when you're on the island! :-) We hope to see you again sometime soon!

Elizabeth St Feb 2020

Reviewed by Julie C. on 2020-03-21
Recommend to Others
Property condition
Location
Cleanliness
Services from rental manager
Overall satisfaction
This property is in a great location while still being private. This is our second year at this house, and will be coming next year. The management is friendly and responsive. I would say that the house is very tired and needs updating. A deep cleaning, replacing tattered and worn furniture and a paint job throughout would work wonders.

Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest

Unit Code: 320E

Tropical Jewel

Colorful and Quirky 2BD/2BA Key West Home near Historic Seaport - Monthly Rental
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the city anytime you want, or quickly retreat back when the party is winding down. Discover the eclectic charm of this Key West home, just two blocks from the Historic Seaport. This unique property is a perfect blend of colorful, quirky elements that embody the spirit of island living. Relax on the front porch in Adirondack chairs while enjoying a cold beverage. Inviting and Eclectic Living Spaces: Our living room is a cheerful space, ideal for relaxing with a good book or sharing stories of the day's adventures. Casual and relaxing colors touch the home's eclectic decor. The open-concept living and kitchen area provides a comfortable and inviting environment for you and your guests, especially when you consider that the living room extends outside to a covered dining area, alfresco dining, wet bar, and a mini fridge creates the perfect place to make your cocktails. The unit's washing machine and dryer are also hidden in a closet in this area. Outdoor Living at its Quaintest: Step out onto the covered lanai, an ideal spot for enjoying meals or a cool drink. It's a true highlight of the property, providing just the right amount of space for a gathering. The pool, a good size for Key West standards, offers a delightful retreat from the warm sun in a serene backyard setting. The pool is private and heated for when the temperatures are slightly more brisk. Functional Kitchen and Dining: The kitchen features granite countertops alongside distressed cabinets, creating a practical yet charming space for meal preparations. The fridge, range and dishwasher ensures your stay is convenient and enjoyable. Accommodations: This home accommodates up to 6 guests but 4 comfortably with 2 Queen beds and 1 Full-size bed. The loft space above the primary bedroom adds a unique touch but is more suited for shorter stays or as an additional, temporary guest space as the ladder up there may be difficult for some people. Embrace the vibrant, quirky charm of our home, where each day is an opportunity to create unforgettable memories in Key West. Book now before the property is no longer available. Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. NOTES: Pets considered. This home does not come with a dedicated parking place. Monthly Rental Only (This property must be rented for 28 or more days by city ordinance)
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Age 24 and under.
DatesPrice
03/01/2026 - 05/31/2026$306 /nt
03/01/2026 - 05/31/2026$441 /nt
03/01/2026 - 05/31/2026$9,900 /month
06/01/2026 - 08/31/2026$306 /nt
09/01/2026 - 11/30/2026$306 /nt
09/01/2026 - 11/30/2026$9,169 /month
09/01/2026 - 11/30/2026$9,175 /month
12/01/2026 - 02/28/2027$331 /nt
12/01/2026 - 02/28/2027$493 /nt
12/01/2026 - 02/28/2027$10,076 /month
12/01/2026 - 02/28/2027$10,087 /month
03/01/2027 - 05/31/2027$474 /nt
03/01/2027 - 05/31/2027$493 /nt
4.8571
(14 Review)

Awesome month at Tropical Jewel

January 2026
, Wausau, WI United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

This was really an awesome location, surprisingly quiet, given its location, close to the action in Key West, and extremely well kept. Really had a fabulous experience, well stocked, and perfect size for our needs. The management company was very responsive to needs, and our day was wonderful.

Great house in a fantastic location....however

December 2025
, Hilton Head, SC United States

Overall
4
Property condition
4
Location
5
Cleanliness
4
Services from rental manager
3

Great little house on a quiet street just a few short blocks from Duval. Enjoyed the pool nearly every day and although some of the furnishings are looking a bit worn, the house was clean and comfortable for our month long stay. However a word of warning, you should be aware that the utility charge at the end of your stay will far exceed your expectations.

Tropical Jewel was better than we expected.

November 2025
, Ft Worth, TX United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

We loved Tropical Jewel. Private pool was awesome. Fully furnished house and kitchen.Great walkable location.

Easy Living in Key West

March 2025
, Pompton Plains, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

Third time renting Tropical Jewel. Great location and great pool. Angela from Preferred Properties was a pleasure to deal with. Any questions we had she immediately answered.

Great stay at Tropical Jewel!

January 2025
, Wausau, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

House was perfect! Great backyard oool, quiet street, perfect location!

Great Location and Great Customer Service

December 2024
, Clayton, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Property was even better than described. Great convenient location to EVERYTHING! Management company responded with any questions to any of our needs. I would definitely stay here again and recommend anyone to stay at this property.
Pool and Covered Porch was a great asset!!

Great Location and Great Customer Service

December 2024
, Clayton, NC United States

Overall
5
Property condition
5
Location
5
Cleanliness
5
Services from rental manager
5

Property was even better than described. Great convenient location to EVERYTHING! Management company responded with any questions to any of our needs. I would definitely stay here again and recommend anyone to stay at this property.
Pool and Covered Porch was a great asset!!

Beautiful Oasis

October 2024
, Aylesbury, BKM United Kingdom

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

I can’t express how much I love this house.
We stayed for a month in October and really really didn’t want to leave.
As our driver arrived I touched the house and said ‘ we ll be back’ it may sound bonkers !

The booking process was simple and Angela at PP was a dream to deal with, keeping us up to date with any changes etc
Communication was fantastic

Anyway the arrival was simple and the electronic door locks meant no one needed to carry keys which was a bonus.
The accommodation was spotless and spacious. The kitchen was well equipped and organised and the overall decor was sunny and tropical.
Having tvs in each bedroom meant we could have some freedom from watching same old programmes. Also the highlight for me was watching a programme called ‘Midsommer Murders’ whilst being outside in the pool. The outdoor tv was awesome!

Both bedrooms had a bathroom / shower each. We didn’t use the mezzanine bedroom (only to store our luggage). However kids would love this area.

My favourite area was the pool deck and outdoor cocktail kitchen!
The pool was heated and larger than i expected which is unusual in KW.
It is private and is surrounded by lush foliage which brings nature into the garden which was wonderful.
I wish i could share a couple of pics but there doesn’t seem to be an option.

The location was perfect , close to the Seaport and Duval but quiet. Also close to Faustos who told us we could wheel our shopping home in the trolley as long as we returned it!! That’s how close.

Finally i d like to say it has the perfect balance of luxury and comfort and please can we come back.


Hidden gem

April 2024
, Vestavia, AL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Convenient location in a quiet neighborhood, but close to the harbor and restaurants. Private backyard with a beautiful pool. Rental company is very responsive. Only downside is the guest bedroom is small.

Lovely Home

January 2024
, Traverse City, MI United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This sweet house is in a great location - all of our favorite places within walking or biking distance. Neighborhood quiet, except for the roosters of course! We love working with the staff at Preferred Properties - Angela is amazing.

Manager's Response

Thank you for the kind words and we look forward to hosting you again in the future.

Great Location and Great House

December 2022
, Arkadelphia, AR United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The house was in the perfect location, perfectly clean with a wonderful pool. We loved our stay here, and always love working with Preferred Properties!

Excellent

June 2022

Overall
5

Very nice and private plus close to attraction.

November 2020

November 2020
, Fort Lee, NJ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is my second time renting the Tropical Jewel and it is was again an absolutely a fabulous rental property. Every morning I made a pot of coffee and sat in the yellow lounge and felt the sweet island breezes and the sounds of Key West. The house is 2 blocks off Duval - great for taking in the sights. A quaint little cottage and the pool is wonderful. The property managers (Angela, Phil, and Meghan) were there at a moments notice to answer questions or take care of any problems that might arise. I would highly recommend this property!!

Manager's Response

Diane, You made our jobs easy. Your easy going attitude and love of the Key West lifestyle, combined with an ideal property, ensured that we would excel at providing this wonderful experience to you AGAIN. We also just really enjoy when you're on the island! :-) We hope to see you again sometime soon!

Our slice of Heaven .....

March 2019

Overall
5

Loved the Tropical Jewel -- location, pool, the privacy, the yard!

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2 Bed
2 Baths
Sleeps 6

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