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.
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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
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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
Enjoy your private front porch in this quiet neighborhood in Old Town Key West. Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home with a shared pool on property.
Old Town
Stop searching, Conch Wind is the rental home in Key West you have been hunting for!
Ocean Side
This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean.
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
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Old Town
When a name says it all you know you have made the perfect choice for your Key West island escape.
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
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.