Old Town
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!
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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 13 - 24 of 72 results matching your search criteria
Map ViewOld Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Stock Island
Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.
Old Town
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
Old Town
When a name says it all you know you have made the perfect choice for your Key West island escape.
Old Town
Your perfect escape to Key West awaits you in the Land of Love.
Old Town
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
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
Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido!
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.