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 / PoolGrillGated Community
2 Bedrooms
1.5 Baths
5 Guests
Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again
2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West.
Daily - Weekly / PoolGated 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 RentalPoolGrillPets Allowedpets considered
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.
30 Day RentalPoolGrillPets Allowedpets considered
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 RentalPoolGated CommunityPets Allowedpets considered
2 Bedrooms
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you find your dream come true spacious vacation rental home
Daily - Weekly / PoolGated Community
2 Bedrooms
2.5 Baths
6 Guests
For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer!
Daily - Weekly / PoolGrillGated 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 RentalPoolGrillPets Allowedpets considered
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 / PoolGrillGated Community
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
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 RentalGrill
2 Bedrooms
2.5 Baths
6 Guests
Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer!
Daily - Weekly / PoolGated Communitypets not allowed
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