Old Town
Your perfect escape to Key West awaits you in the Land of Love.
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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 34 results matching your search criteria
Map ViewOld Town
Long considered a sign of hospitality, the pineapple is widely recognized as sign of Welcome and Friendship, and so we welcome YOU to the Perfect Pineapple!
Old Town
Key Lime Pie is a private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.
Old Town
A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year.
Old Town
Searching for an affordable monthly vacation rental in the heart of Key West? Do you plan on spending most of your time enjoying all that Key West has to offer and seeing what if feels like to really live like a local? Then tune into Windchime!
Old Town
A quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
Old Town
Lovely 1 bed, 2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
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
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
Make your next Florida vacation something special with this charming home in a quiet, upscale enclave that is close to everything!
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.