Mid Town
Meander down a quiet street in midtown Key West until you come upon a white picket fence on a shady corner lot. Park and walk around to open the gate.
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.
Displaying 37 - 48 of 72 results matching your search criteria
Map ViewOld Town
Enjoy a carefree vacation in 2 bedroom 1.5 bath, 2-story town home, located on Southard Court in the Truman Annex, downtown Key West. This home is situated right in front of the community pool.
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.
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
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!
Stock Island
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.
Old Town
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
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
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.
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
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!