View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!
All Units On Special
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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.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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.
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
When a name says it all you know you have made the perfect choice for your Key West island escape.
Your perfect escape to Key West awaits you in the Land of Love.
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
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!
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.