Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!
All Units On Special
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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.
Casita de Catherine is a hidden gem! Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West.
This great 2 bedroom, 2 bathroom, Key West condo located at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve.
Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.
Coral Breeze is a two bedroom town home located in the gated community at the Key West Golf Club on Stock Island. This modern and comfortable home is perfect for a couple or small family looking to stay for a month in Key West.
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.
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!
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.
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.
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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.
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.