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
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 Allowed
3 Bedrooms
2 Baths
6 Guests
Welcome to a golfer’s paradise at Spa Oasis!
30 Day RentalPoolGrillWasher/DryerGated Community
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 Allowed
2 Bedrooms
1 Bath
4 Guests
Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo offers peace, quiet and convenience.
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
3 Bedrooms
4.5 Baths
8 Guests
Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home.
30 Day RentalPoolGrillWasher/Dryer
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 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
30 Day RentalPoolWasher/Dryer
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 RentalGrillGated Community
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
1.5 Baths
5 Guests
Located on the main road meandering through the secluded gated Key West Golf Club community, you’ll find A Little Slice of Paradise. Spend a month (or two) in this charming townhouse and you may never return home.
30 Day RentalPoolWasher/DryerGated CommunityPets Allowed
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