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 61 - 72 of 72 results matching your search criteria
Map ViewOcean Side
Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time. How about an evening stroll through the tropical jungle in your own backyard.
Old Town
When a name says it all you know you have made the perfect choice for your Key West island escape.
Old 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
View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!
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.
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
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.
Ocean Side
Enjoy spectacular ocean views from this lovely rental!
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Stock Island
This cozy 2 bedroom home is nestled in the center of the Key West Golf Club on a secluded lane.