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 25 - 36 of 72 results matching your search criteria
Map ViewStock Island
Situated in the gated community at the Key West Golf Club, Wind Swept is a perfect retreat for a small family or two couples looking for a monthly rental.
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
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
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.
Old Town
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.
Old Town
Your perfect escape to Key West awaits you in the Land of Love.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.
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.
Stock Island
Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key West!
Old Town
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.
Old Town
**** PLEASE NOTE **** THE SHIPYARD POOL WILL BE CLOSED THE WEEK OF SEPTEMBER 7th THROUGH SEPTEMBER 14th FOR RESURFACING.