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Island Pearls
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About
Looking for the perfect spot to soak up some sunshine and unwind in Key West? You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one).
Step inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun.
The living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring.
Both bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together.
Outside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise.
Island Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great 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.
P.S. The pool is all yours—no sharing here! Pool heat available when requested.
Features
Amenities
- Outdoor Shower
- Air Conditioning
- Internet
- Iron & Board
- Linens Provided
- Parking
- Coffee Maker
- Kitchen
- Microwave
- Toaster
- Dining Table
- Deck / Patio
- Fenced Yard
- non smoking only
- pets not allowed
- Near Beach
- Close to Town
- Full Kitchen
- Cookware
- Blender
- Outdoor Grill
- Dishwasher
- Linens
- Washer & Dryer
- High Speed Internet
- Wifi
- Assigned Parking
- Gas Grill
- Deck
- Cable TV
- Smart TV
- Dedicated Parking Space
Property Type
- House
Stay Duration / Location
- Nightly
- Any Duration
- Key West
Pools and Hot Tubs
- Fenced Pool
- Heated Pool
- Pool
- Private Pool
Availability
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Map
Reviews
Leave a ReviewAnother Great Stay In KW
Teresa A., Oklahoma City, OK United States
Beautiful, high-end, private, convenient historic cottage
Chris P., Fort Denaud, FL United States
From the time of booking, the management company stayed in contact with me via email and text. When we arrived at the cottage, we were all very pleased. It was beautiful and the layout worked perfectly. Love the high-end touches, and attention to detail. It was private, yet close to the action on Duval Street. The grocery store across the street is very convenient. We appreciated the off street parking because we left the car and walked everywhere. It was so nice having our own front porch and back yard oasis. We didn't want to leave, and plan to go back and stay again!
Wonderful stay!!
Tiffany Z., Grand Rapids, MI United States
We loved our stay at Island Pearl! It is in such a convenient location, but tucked away from the busy street when you need to relax. A small grocery store is right outside the door which was so convenient! We enjoyed the pool for a couple hours each day. The home seems to be recently remodeled and is tastefully decorated with all the modern appliances and items needed to enjoy your stay.
It is right downtown so be prepared for street noise here and there but we used a small sound machine and it wasn’t an issue. The beds are super comfy!
The property management team was extremely helpful and communicated quickly when we had questions. We also couldn’t figure out the coffee maker and they came over right away to help us out. We wouldn’t hesitate to rent this property again. Great for 2 couples since there are two almost identical suites.
A rental car is not needed as it’s easily walkable and Ubers are readily available at any time without even a wait. Definitely check out the French restaurant called Marquesa it was incredible and don’t miss Sunny Eggs for coffee, pastries and incredible breakfast/lunch options.
Island pearl more like diamond
Sue Ann W., athens, AL US
Everything was great! Comfortable beds, clean and well taken care of. Property management was quick to respond to our needs. Truly enjoyed this property.
Great place in perfect location
Jim D., Supply, NC US
Had a wonderful time and the rental was like new and good location. Property mgr was easy to communicate with.
Amazing Trip
Pam F., prattville al, AL US
This unit was amazing! The location was perfect-just 2 blocks from Duval St., short walk to the Marina and less than a mile to the Southernmost Point. It was immaculate - kitchen appliances were 5 star.
location location location
Recent Guest, weaverville, AL US
Amazing location, luxury accommodations. Everything you needed is supplied. Fantastic communication and service. Very clean and comfortable. see you next year!!!
Fantastic gem in Old Town
Recent Guest, Las Vegas, NV US
Everything about this rental was top notch. House seems recently renovated and rooms are tastefully decorated. Location is perfect as you can walk down either direction in Duval Street. Our little one loved the heated pool. Last but not least, Preferred Properties was very accommodating and super responsive!
Everything and More!
Patti S., Conway, AR US
Not often are our expectations exceeded when renting a vacation home, but oh my goodness this place is the best. Two couples stayed comfortably. The location is fabulous, especially the grocery store across the street. Several area restaurants were all great. And the bookstore - well let's just say it became my new favorite place. The cherry on top was a dedicated parking space adjacent to the home. We would all give this location 10 stars if possible!
Wonderful!!!! Perfect house!!!
Randi D., Fair Play, SC US
This house is perfect for 2 couples. The bedrooms and bathrooms are large. Kitchen has new appliances and the pool is beautiful! Perfect location to walk to attractions and restaurants. On a quiet street across from a grocery. Loved this house!!!!
Awesome Ley West House
Laura T., Grosse Pointe Shores, MI US
The place was beautiful and location superb!
Perfect place to stay in Key West
Best Rental Property in Key West
David B., Van Buren Twp, MI US
The house was modern with new appliances. The king size beds were comfortable. The walk in showers were spacious. The private pool was an oasis at the end of a busy day. And the location was perfect. Definitely staying here again.
Great place to stay
Recent Guest, Julian, CA US
The home was beautifully decorated and a great location. We were able to walk to everything. There was even a grocery store across the street. The property management company was very helpful. I would definitely recommend staying at this beautiful home!
Awesome Home
Recent Guest, Alpharetta, GA US
Great location, beautiful home and wonderful pool!
Awesome Home
John H., Alpharetta, GA US
Great location, beautiful home and wonderful pool!
Great house in great location!
Recent Guest, Berwick, LA Unknown
We loved the house. It was clean, well maintained, and in a great location! We loved having the grocery store across the street and walked or rode bikes to everything!
First time Key West visit
Brandon W., Fort Worth, TX US
Beautiful historic home one block off Duval. Beautiful renovation appears to be very recent. The pool is great to take a break from the heat.
Key West 2025
Josh B., Texarkana, TX US
Great spot. Clean place. Great pool.
Nice updated unit in perfect location
Terry M., Frisco, TX United States
This was a great property in the perfect location! The updates to this unit really make it feel special. And Angela was very accommodating and communication was timely. The only issue we had was the upstairs renters could be heard walking all hours of the night (midnight and 3am).
Key west
Recent Guest, Villa Hills, KY US
Right in middle of it all, new kitchen equipment, nice interior, easy walking everywhere or get a golf cart and really explore then come back and relax in private pool.
1st but not last trip to the Keys!
Recent Guest, Rutledge, TN US
Loved our stay at Island Pearls! Great location and very clean!
Florida National Park Trip
Recent Guest, Sanford, FL US
This Home is Beautiful inside & out! Incredible Family Room, Kitchen and two bedrooms all decorated beautifully! In a great area, walkable to everything including a grocery store across the street! Would definitely stay here again!
Beautiful property!
Angie G., Lexington, SC United States
This is a beautiful newly renovated property. It was perfectly located within walking distance of Duvall Street. It has a great front porch for people watching. Is directly across the street from a great little grocery store, which is super convenient. The kitchen is great if you like to cook and it has an awesome set up for coffee. The backyard is perfect for relaxing, but you should know there is also a small cottage behind the house that is a separate rental property. Apparently, if it is rented at the same time as this property, you would be sharing the swimming With strangers. That did not happen to us, but we also did not know it was a possibility until we were already there. The listing should be very clear about this, but it’s not. The property management company was very helpful with any questions we had and super responsive. I would definitely stay here again.
Manager's Response
Thank you for the suggestion! The pool is now exclusive to the unit you rented, though there is a long-term rental apartment upstairs. However, the pool remains solely for the main unit’s guests.
Excellent Rental
Nichole V., Naples, Fl United States
We had an absolutely wonderful stay at Island Pearls. The location could not have been better to enjoy the nightlife of Key West. The home was absolutely immaculate with very comfortable and top-of-the-line amenities. We didn't have a chance to use the pool but that and the driveway are a major bonus! The grocery store across the street came in quite handy as well. Note to the owner: This appears to be a newer rental and clearly a lot of thought went into the comfort of your guests. A few things to make their stay easier would be beach/pool towels. There was only one in the house. An iron/steamer combo would be great as most traveling are dressing out of a suitcase. And also some baking sheets for the oven would be a nice addition to the kitchen. This truly was the best home we've rented and we travel ALOT! We will definitely seek out this home again when we visit Key West. Thank you for the great accomodations!
Beautiful oasis near everything
Charlie L., TAMPA, FL US
The 2 bed/2 bath home is in impeccable condition and perfectly decorated with high-end appliances and furnishings. Three, count them, three coffee makers to cover all your early morning needs (espresso, drip, or Keurig). Great places to eat within 50 yrds, and a quick walk to Duval or Historic Seaport. Do not hesitate to book a stay at Island Pearls!
Best vacation rental near Duval Street!
Stacy, Loxahatchee, Florida United States
Island Pearls is absolutely beautiful! Everything that you need for a perfect Key West vacation is waiting for you as soon as you walk in the door. This unit has two bedrooms with ensuite bathrooms, featuring the most comfortable beds, designer features including spacious closets that light up as you open the doors, and gorgeous, spacious showers.The living area has ample comfortable seating along with a large wall mounted smart tv. The kitchen is equipped with modern upscale appliances and all of the extras that you don't find in other vacation rentals. Use the Vitamix blender to whip up a batch of margaritas. Chill your wine in the separate wine fridge below the coffee bar that includes an espresso maker, Keurig, and a drip coffee pot. Plenty of cookware, dinnerware, cutlery, drinking glasses and stemware can be found in the beautiful large white cabinets that extend up to the high ceilings. There is seating for four at the countertop and a large table with six comfortable chairs as well. The apartment features lots of natural light when you open up the plantation shutters, and also designer light fixtures for evening use.The private back patio features a table and chairs, sun loungers, and a gas grill. The star of the patio is the large swimming pool. It was so refreshing to relax in after a day of sightseeing or shopping.The location of Island Pearls cannot be beat! It is only a block away from the stores, restaurants, and bars of Duval Street, and is in walking distance of the Historic Seaport, Mallory Square, beaches, and the attractions in Old Town. Fausto's Food Palace is right across the street, where you can shop for anything you need in the way of food, beverages, toiletries, etc.We enjoyed drinking our morning coffee everyday in the rocking chairs on the front porch.I can't think of a better place to stay at while vacationing in Key West, whether you are staying for a few days or a few months.

The Property Management was very great about communicating prior to our stay. The house has recently been renovated and is comfortable. I gave 4 stars for maintenance since the pool deck has some boards that need replacing. The pool itself is wonderful. The property is across the street from the grocery store-great for running over for a forgotten item. But, being across the street they get a lot of traffic and noisy early morning deliveries. Nothing that would prevent us from staying here again.