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 49 - 60 of 72 results matching your search criteria
Map ViewOld Town
Perfect for large families or groups of friends, this property offers great amenities including a private pool, open floor plan, 2 kitchens and a large laundry room, right downtown Key West.
Old Town
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.
Old Town
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.
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
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
Settled in a small community in Old Town, only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental.
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.
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
Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
Stock Island
This cozy 2 bedroom home is nestled in the center of the Key West Golf Club on a secluded lane.