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
3 Baths
6 Guests
This charming, clean and nicely decorated vacation rental home is located in Coral Hammock, one of Key West newest communities, very close to restaurants, boating and water adventure!
30 Day RentalPoolGrillWasher/DryerGated Community
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
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
4 Bedrooms
3.5 Baths
8 Guests
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
1.5 Baths
6 Guests
Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. All that and much more awaits you at Windswept!
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool.
30 Day RentalPoolGrillWasher/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
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!
Daily - Weekly / PoolGrillWasher/Dryer
2 Bedrooms
2.5 Baths
6 Guests
Rooftop community just steps away from Duval Street to great restaurants, shopping and entertainment.
The pool will be completely shut down during July 8-19 due to pool resurfacing and repair of pool skimmers
30 Day RentalPoolWasher/DryerGated CommunityElevatorPets Allowed
2 Bedrooms
1 Bath
4 Guests
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home! There is no need to look any further for your dream come true vacation rental!
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
6 Guests
Key West is all about the beach and the ocean! Located right by Smathers Beach, this tastefully decorated rental might just be the answer!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityElevator
2 Bedrooms
2 Baths
5 Guests
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.
Daily - Weekly / PoolWasher/DryerGated Community
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