Old Town
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home!
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All of the rentals below have at least one available deal or discount, which can vary depending on when you book or when you plan to take your trip. Just click on the Explore All Specials button next to each listing to see the terms of the available deals. Searching your stay dates will show you all properties that have an available deal during that time. You can also view all of our current promotions and see the details of each one on our main Deals page.
Displaying 37 - 47 of 47 results matching your search criteria
Map ViewOld Town
Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!
Mid Town
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
Enjoy a carefree vacation in 2 bedroom 1.5 bath, 2-story town home, located on Southard Court in the Truman Annex, downtown Key West. This home is situated right in front of the community pool.
Ocean Side
Enjoy spectacular ocean views from this lovely rental!
Stock Island
Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key West!
Old Town
A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
Old Town
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.