Key West Vacation Rentals
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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!
Located in a quiet community of Windward Park, only a short walk to Duval Street, with a large shared pool, Island Wind is a true gem in between our rentals
Welcome to a tropical sun drenched oasis in the heart of Old Town Key West.
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets Not Allowed
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevatorFitness CenterTennisPets Not Allowed
Steps away from the large lagoon style pool surrounded w/lush tropical landscape.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets AllowedPet Considered
Location, location, location! Practically overlooking famous Duval Street from large upstairs deck!
Daily - Weekly / PoolGrillWasher/DryerFitness CenterTennisPets Not Allowed