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
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.
30 Day RentalPoolGrillWasher/Dryer
2 Bedrooms
1 Bath
5 Guests
Enjoy your morning coffee, afternoon cocktail or freshly grilled fresh catch on the outside patio when taking a break from exploring Key West!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityFitness Center
2 Bedrooms
1 Bath
4 Guests
LOCATION YOU CAN NOT BEAT! Located right in the heart of Old Town yet on a quiet lane, only steps to Duval Street, Blue Heaven and many other restaurants and little boutiques!
30 Day RentalGrillWasher/DryerFitness CenterGolfTennisPets Not Allowed
2 Bedrooms
1.5 Baths
5 Guests
Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well!
Daily - Weekly / PoolWasher/DryerGated CommunityFitness CenterPets Not Allowed
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.
30 Day RentalPoolGrillPets AllowedPet Considered
3 Bedrooms
2 Baths
8 Guests
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
2 Bedrooms
2 Baths
4 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
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
2 Bedrooms
1 Bath
4 Guests
Just steps away from the pool! Recently remodeled, tastefully decorated. This rental is hard to beat!
Daily - Weekly / PoolWasher/DryerGated Community
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 AllowedPet Considered
3 Bedrooms
2.5 Baths
6 Guests
Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
2 Bedrooms
2.5 Baths
6 Guests
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.
30 Day RentalPoolWasher/DryerGated CommunityElevatorPets AllowedPet Considered
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