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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.
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless private Conch home.
30 Day RentalPoolGrillWasher/Dryer
For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the logical choice!
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
30 Day RentalPoolGrillWasher/DryerPets Allowed
Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.
30 Day RentalPoolGrillWasher/DryerGated Community