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.
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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 37 - 48 of 72 results matching your search criteria
Map ViewOld Town
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.
Old Town
Located in Bahama Village, a quaint neighborhood in Old Town Key West, this beautifully renovated conch home is a romantic island getaway. This rental is a guest house situated in the back yard of a private residence.
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.
Old Town
Your perfect escape to Key West awaits you in the Land of Love.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.
Old Town
Tumi’s Time Out is a 2-bedroom, 2-bathroom town-home in the sought after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes.
Old Town
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.
Old Town
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!
Old Town
Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.