Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key West!
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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.
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean.
Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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.
The historic brick foundry residence is in the luxurious gated community of the Truman Annex, appropriately named after President Harry Truman.
This spacious home with a large outside deck is tucked away on a quiet lane in the Truman Annex, yet only a short walk to all attractions.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Recently remodeled, tastefully decorated. This rental is hard to beat!
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.