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!
1 Bedroom
1.5 Baths
4 Guests
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything you can expect from a perfect Key West rental
Daily - Weekly / PoolGrillGated CommunityFitness CenterPets Not Allowed
2 Bedrooms
2 Baths
4 Guests
Perfect rental for a small family or couple of friends, close proximity to the pool and beach, Conch Condo makes one of the most desirable vacation rentals
A two-bedroom, two-bath condo in Truman Annex.
Daily - Weekly / PoolWasher/DryerGated Community
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
2 Bedrooms
1 Bath
4 Guests
Here is your perfect opportunity to enjoy your stay in one of the most popular complexes of Key West, Truman Annex!
Daily - Weekly / PoolWasher/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
2 Baths
5 Guests
Unbeatable location! Only a block to famous Green Parrot bar yet in a secluded, quiet community of Truman Annex
Daily - Weekly / PoolWasher/DryerGated Community
3 Bedrooms
3 Baths
6 Guests
Private conch home in a quiet neighborhood but still within walking distance to all of the Key West sites.
30 Day RentalGrillWasher/DryerPets AllowedFitness CenterPet Considered
2 Bedrooms
2 Baths
6 Guests
Imagine swimming in the Olympic size pool and enjoying a spectacular view of Atlantic Ocean at the same time!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevatorFitness CenterPets Not Allowed
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPoolWasher/Dryer
2 Bedrooms
1.5 Baths
4 Guests
Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport.
30 Day RentalGrillWasher/DryerFitness Center
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 / PoolWasher/DryerGated Community
2 Bedrooms
2.5 Baths
4 Guests
Steps away from the large lagoon style pool surrounded w/lush tropical landscape.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets AllowedPet Considered
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