Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
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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
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Recently remodeled, tastefully decorated. This rental is hard to beat!
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
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
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 one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life.
Old Town
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.
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
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
Stock Island
Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story town home located in the private gated community of Coral Hammock on Stock Island.
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.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.