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!
1 Bedroom
1 Bath
4 Guests
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach
Daily - Weekly / PoolWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunbathe, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
2 Baths
6 Guests
Imagine swimming in the Olympic sized pool and enjoying a spectacular view of the Atlantic Ocean at the same time? How about an evening stroll through the tropical jungle in your own backyard?
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
2.5 Baths
6 Guests
Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything!
Daily - Weekly / PoolWasher/DryerGated CommunityElevator
2 Bedrooms
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
CONCH WIND - Stop searching, Conch Wind is the rental home in Key West you have been hunting for!
Daily - Weekly / PoolWasher/DryerGated Community
3 Bedrooms
2 Baths
8 Guests
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2 Baths
4 Guests
Key Lime Pie is the private cottage that perfectly encompasses the “Key West vibe” that you’re looking for. The minute you walk in to see the bright, sunny walls and local artwork, you know you are somewhere special.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.
30 Day RentalPoolGrillWasher/DryerPets Allowed
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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