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!
2 Bedrooms
2.5 Baths
4 Guests
Steps away from the large lagoon style pool surrounded w/lush tropical landscape.
30 Day RentalPoolGrillGated CommunityPets Allowedpets considered
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
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
3 Baths
8 Guests
Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home!
Daily - Weekly / PoolGated CommunityPets Allowedpets considered
2 Bedrooms
1 Bath
4 Guests
Come enjoy one of Key West's most desirable rental complexes, Truman Annex. Conveniently located just couple blocks to the beach, Duval Street and Mallory Square, makes this the ideal rental for a small family or couple of friends
Daily - Weekly / PoolGated Community
3 Bedrooms
3 Baths
6 Guests
Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you!
Daily - Weekly / PoolGated Community
1 Bedroom
1 Bath
2 Guests
NEWTON'S NEST (Monthly Rental)
30 Day RentalPool
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
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunburn, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillGated CommunityElevator
2 Bedrooms
2.5 Baths
6 Guests
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!
Daily - Weekly / PoolGated CommunityElevator
2 Bedrooms
2.5 Baths
4 Guests
You are so close to the large community pool that you will be able to hear the waterfall in this beautifully landscaped area.
30 Day RentalPoolGated 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
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