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 Baths
6 Guests
This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants.
Daily - Weekly / PoolGrillWasher/DryerGated Community
3 Bedrooms
3.5 Baths
7 Guests
Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you!
Daily - Weekly / PoolGrillWasher/Dryer
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
2 Bedrooms
1.5 Baths
4 Guests
Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch
Daily - Weekly / PoolGrillWasher/DryerGated Community
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 RentalPoolGrillWasher/Dryer
2 Bedrooms
1.5 Baths
6 Guests
Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off.
30 Day RentalPoolWasher/DryerGated CommunityPets Allowed
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
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 RentalPoolGrillWasher/DryerGated Community
1 Bedroom
2 Baths
2 Guests
Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
30 Day RentalGrillWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!
Daily - Weekly / PoolGrillWasher/DryerPets Allowed
2 Bedrooms
1.5 Baths
4 Guests
Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
1 Bath
4 Guests
This gorgeous apartment is located in one of Key West's most attractive, quiet, and convenient neighborhoods, Truman Annex, close to many attractions and also Fort Zachary Taylor Beach
Daily - Weekly / PoolGrillWasher/DryerGated Community
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