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 Baths
6 Guests
Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cottage with fully fenced yard makes a perfect rental for a small family or few friends trying to make the best of Key West!
Daily - Weekly / GrillWasher/DryerPets Allowed
1 Bedroom
2 Baths
2 Guests
Private fenced outdoor space to enjoy your private plunge pool and the large outdoor space for lounging and dining.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2.5 Baths
4 Guests
Beautifully restored private cottage located in Old Town Key West.
30 Day RentalWasher/DryerPets Allowed
1 Bedroom
1 Bath
2 Guests
Enjoy your private front porch in this quiet neighborhood in Old Town Key West.
Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home.
30 Day RentalPoolGrillPets Allowed
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
2 Baths
5 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
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 Community
1 Bedroom
2 Baths
2 Guests
If privacy is what you desire this is the property for you. Completely set back from street and fenced for you to enjoy your private pool and large outdoor space.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
1 Bath
4 Guests
You are instantly soothed walking through the door of the Lavender Jungle, located in the Truman Annex, one of Key West's most attractive, quiet, and convenient neighborhoods.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Sunrise, sunbathe, sunset, repeat! Enjoy spectacular ocean views from this lovely rental!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
2.5 Baths
4 Guests
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
1 Bath
3 Guests
Private outdoor space to enjoy this unique cottage within walking distance of great restaurants and shops.
30 Day RentalPoolGrillPets Allowed
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