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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.
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.
30 Day RentalPoolWasher/DryerGated CommunityElevatorPets AllowedPet Considered
Sit along side your private pool for morning coffee or your evening glass of wine.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
Beautifully restored private cottage located in Old Town Key West.
30 Day RentalWasher/DryerPets AllowedOutdoor ShowerPet Considered
With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying.
30 Day RentalPoolGrillWasher/Dryer
This unique 1 bedroom, 2 bath cottage is about to become your home away from home!
Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE!
30 Day RentalPoolWasher/DryerPets Not Allowed