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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 - 48 of 72 results matching your search criteria
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Stock Island

Coral Garden is a two bedroom town home in the quiet gated community of Coral Hammock located on Stock Island. Perfect for families or those who are working from home. Close to all that Key West has to offer.

Ocean Side

Enjoy spectacular ocean views from this lovely rental!

Old Town

Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.

Old Town

View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!

Stock Island

Situated in the gated community at the Key West Golf Club, Wind Swept is a perfect retreat for a small family or two couples looking for a monthly rental.

Old Town

**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.

Old Town

Your perfect escape to Key West awaits you in the Land of Love.

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.

Old Town

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.

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.

Stock Island

Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key West!

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