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!
4 Bedrooms
3.5 Baths
8 Guests
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Located in the quiet neighborhood of The Meadows, you’ll find the Conch Republic Retreat, a quintessential cigar maker’s shotgun style house, circa 1890.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
1.5 Baths
4 Guests
It wasn't that long ago that President Truman took casual walks in this same location- now it's your turn! President's Walk exudes luxury and elegance with lots of upgrades and plush furnishings with your every comfort in mind.
Daily - Weekly / PoolGrillWasher/DryerGated Community
0.5 Bedrooms
1 Bath
2 Guests
Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime!
30 Day RentalGated Community
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
1.5 Baths
5 Guests
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation!
Daily - Weekly / PoolGrillWasher/DryerGated Community
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 / PoolGrillWasher/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
2.5 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
4 Guests
Located above the world-renowned Wyland Gallery of Key West, this roof top getaway is the ideal spot for the sophisticated, discerning traveler.
Daily - Weekly / Washer/DryerPets Allowed
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
1 Bath
4 Guests
The location of La Casita cannot be beat -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street.
30 Day RentalGrillWasher/Dryer
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