Old Town
Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!
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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 25 - 36 of 72 results matching your search criteria
Map ViewOld 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!
Stock Island
Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.
Stock Island
Located in the Sanctuary of the gated community in the Key West Golf Club, this spacious single-family home welcomes you to the laid-back island life with the ease of everything on one floor.
Stock Island
Find serenity in this pleasant and spacious home with tons of Key West charm. Featuring an abundance of back yard space for lounging or entertaining, you will not want to leave this lovely retreat.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
Old Town
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
Ocean Side
This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.
Old Town
Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
Old Town
Casita de Catherine is a hidden gem! Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West.