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!
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 RentalPoolGrillPets Allowedpets considered
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 RentalPoolGrillGated Community
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 RentalPoolGrill
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 RentalPoolGrillPets Allowedpets 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 RentalPoolGrillPets Allowedpets 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 RentalPoolGrillGated 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
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
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 RentalPoolGrill
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
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.
30 Day RentalPoolGrillPets Allowedoutdoor showerpets considered
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.
30 Day RentalPoolGrillGated Community
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