Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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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 1 - 12 of 72 results matching your search criteria
Map ViewStock Island
Welcome to your home away from home in Key West. This lovely town home is located in the Key West Golf Club Community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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
Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!
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
Situated on Key West's historical Whitehead Street is Spanish Lime Cottage, appropriately named for one of the lime trees in the back yard. Whitehead runs parallel to Duval Street and is right in the heart of 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
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.
Mid Town
Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly.
Old Town
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.