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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
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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.

Old Town

Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach.

Old Town

Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.

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

Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!

Old 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!

Old Town

It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.

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

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.

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