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
6 Guests
In a small gated community this perfect cottage with a large private deck to allow all the privacy you would need to grill, dine and lounge.
30 Day RentalPoolGrillWasher/DryerGated Community
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
3 Bedrooms
2 Baths
6 Guests
Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
2 Bedrooms
2 Baths
4 Guests
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool.
30 Day RentalPoolGrillWasher/DryerPets AllowedFitness CenterTennisPet Considered
2 Bedrooms
2 Baths
4 Guests
Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining.
One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
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 RentalPoolGrillWasher/DryerPets AllowedPet Considered
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West.
Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.
30 Day RentalPoolGrillPets AllowedPet Considered
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
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
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment.
30 Day RentalPoolGrillWasher/DryerPets AllowedPet Considered
3 Bedrooms
4.5 Baths
8 Guests
In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.
30 Day RentalPoolGrillWasher/DryerPets AllowedFitness CenterPet Considered
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