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Caroline On My Mind
Capacity
About
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings.
As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cathedral windows, creating an instant vacation-like ambiance.
There is a flat-top electric stove, two-door refrigerator, and dishwasher available to facilitate your cooking needs. The countertop seating for three also provides a convenient space for dining or socializing while in the kitchen. Overall, the kitchen offers functionality and amenities that will allow you to enjoy preparing meals during your stay.
The guest room is located on the same floor, accompanied by a full shower bathroom and a washer/dryer for added convenience.
One of the standout features of this home is the large balcony that overlooks Caroline Street below. Equipped with fans, the balcony serves as a perfect spot for savoring morning coffee or enjoying cocktails. A four-person table allows for al fresco dining, while you can also engage in people-watching and relish the refreshing evening breezes of Key West.
To access the floor above, a spiral staircase takes you to the treetops, providing a unique vantage point. The primary bedroom on this floor features a queen-sized bed that can be converted into two twins upon request. Additionally, for those who need to work while in paradise, there is a functional desk with great views, enabling mental breaks amidst the scenic surroundings.
Lastly, there's a skylight in the primary bedroom, offering the opportunity for star gazing while lying in bed at night, adding to the enchanting atmosphere of this 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.
Monthly Rental Only
Shared Pool/6 units
Pets Not Allowed
Features
Amenities
- Outdoor Shower
- Air Conditioning
- Internet
- Iron & Board
- Linens Provided
- Coffee Maker
- Kitchen
- Microwave
- Toaster
- Fenced Yard
- non smoking only
- pets not allowed
- Near Beach
- Close to Town
- Full Kitchen
- Cookware
- Blender
- Linens
- Washer & Dryer
- High Speed Internet
- Wifi
- Cable TV
Property Type
- Condominium
Stay Duration / Location
- Monthly or longer
- Monthly Stays Only
- Key West
Pools and Hot Tubs
- Communal Pool
- Heated Pool
- Pool
- Shared Pool
Photos
Availability
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Map
Reviews
Leave a ReviewPerfect location, beautiful place!
Stacy Runnels, Bentonville, AR United States
Perfect Location, Beautiful Property
Stacy Runnels, Bentonville, AR United States
The location of this property is amazing, just 1.5 blocks from Duval and 1.5 blocks from the Harbor. It’s an easy walk to all the hot spots on the island! The inside is gorgeous with a great balcony where I enjoyed my morning coffee and a late night beverage overlooking Caroline St! The private pool was a wonderful oasis for the hot July afternoons. Can’t wait to go back to this piece of Heaven.
Perfect location, Beautiful property!
Stacy Runnels, Bentonville, AR United States
The location of this property is amazing, just 1.5 blocks from Duval and 1.5 blocks from the Harbor. It’s an easy walk to all the hot spots on the island! The inside is gorgeous with a great balcony where I enjoyed my morning coffee and a late night beverage overlooking Caroline St! The private pool was a wonderful oasis for the hot July afternoons. Can’t wait to go back to this piece of Heaven.
Caroline 2026
Recent Guest, BALLSTON SPA, NY US
Great property & location. Easy access to everything in Old Town. Preferred Properties Management easy to work with & very responsive to any issues that may arise.
Perfect for two
John R., Portland, OR United States
Beautiful colonial Key West house in historic Key West. Compact, two-story with two bedrooms, two baths, with counter-table eating, but no dining area.

Everything about this property is perfect! The location is amazing, just 1.5 blocks from Duval and 1.5 blocks from the Harbor! Easy walk to all the great spots on the island! The inside is gorgeous with 2 beds and baths, a fully stocked kitchen, washer/dryer, adorable living room, and a beautiful balcony overlooking Caroline Street where I loved having my morning coffee and a late night beverage. The private pool/hot tub was a perfect oasis for the hot afternoons in July!! Can’t wait to go back to this piece of Heaven!