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!
2 Bedrooms
2 Baths
4 Guests
Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space.
30 Day RentalPoolPets Allowedpets considered
2 Bedrooms
2.5 Baths
6 Guests
Located in Duval Square, rooftop community which is just off Duval Street, easy walking distance to it all! You do not even need a car!
Daily - Weekly / PoolGated CommunityElevator
3 Bedrooms
4 Baths
8 Guests
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home.
The name says it all!
Daily - Weekly / PoolGrillGated Community
2 Bedrooms
2 Baths
4 Guests
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 / PoolGrillGated Community
2 Bedrooms
2 Baths
4 Guests
Private outdoor kitchen to able to enjoy cooking your favorite dish while enjoying the large outdoor space.
30 Day RentalPoolGrillPets Allowedpets considered
2 Bedrooms
1.5 Baths
4 Guests
Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch
Daily - Weekly / PoolGrillGated Community
2 Bedrooms
3 Baths
6 Guests
French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool.
30 Day RentalPoolGrill
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!
Daily - Weekly / PoolGated Communitypets not allowed
2 Bedrooms
1 Bath
4 Guests
Beautiful, recently updated 2 bedroom apartment located in a popular community of Truman Annex, only a short bike ride to Fort Zachary Taylor Beach
Daily - Weekly / PoolGated Community
3 Bedrooms
2 Baths
6 Guests
Private home with large covered outdoor living area overlooking your private pool w/waterfall.
30 Day RentalPoolGrillPets Allowedpets considered
6 Bedrooms
5.5 Baths
14 Guests
With an unbeatable location, two pools and all top of the line appliances Duval Compound is a true find among vacation rental properties
Daily - Weekly / PoolGrill
2 Bedrooms
1 Bath
4 Guests
Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex!
Daily - Weekly / PoolGated Community
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