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
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
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
1 Bedroom
2 Baths
2 Guests
Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.
30 Day RentalPoolWasher/Dryer
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
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.
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
3 Bedrooms
3 Baths
6 Guests
Feel the allure of this spacious home in the center-of-it-all community of the historic Truman Annex!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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
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
3 Bedrooms
2 Baths
8 Guests
Built in 1889 with original Dade County Pine, history comes alive when you enter this luxurious private home.
30 Day RentalPoolGrillWasher/DryerPets Allowed
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