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 Bath
5 Guests
Looking for a peaceful retreat yet close to everything? Ideally located on Southard Street, within walking distance to the beach at Fort Zachary Taylor State Park, Duval Street and Mallory Square, Bayview Harbor is the spot you’ve been looking for.
Daily - Weekly / PoolGrillWasher/DryerGated Community
2 Bedrooms
2.5 Baths
6 Guests
Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido!
Daily - Weekly / PoolGrillWasher/DryerPets Allowed
1 Bedroom
1 Bath
4 Guests
Cozy apartment within biking distance to The Historic Seaport, Cuban Coffee Queen, local grocery store Fausto's and even Higgs Beach
Daily - Weekly / PoolWasher/DryerPets Allowed
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!
Daily - Weekly / PoolGrillWasher/DryerGated Community
3 Bedrooms
3 Baths
8 Guests
Ideal for a family vacation or group of friends looking for a rental on a budget. Located very close to some great Key West restaurants this property is a steal!
Daily - Weekly / PoolGrillWasher/DryerGated CommunityPets Allowed
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
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
30 Day RentalPoolWasher/Dryer
2 Bedrooms
2 Baths
5 Guests
Enjoy breathtaking sunsets with a glass of wine from your own private porch
It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House.
Daily - Weekly / PoolGrillWasher/DryerGated Community
6 Bedrooms
5.5 Baths
14 Guests
With an unbeatable location, two pools and all top of the line appliances Duval Compound is a true find among vacation rental properties
Daily - Weekly / PoolGrillWasher/Dryer
2 Bedrooms
1.5 Baths
6 Guests
Screened porches up and down for you to enjoy the the extra living space in this lovely townhome.
30 Day RentalPoolGrillWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Located in the historic Bahama Village neighborhood, nestled amongst the palms, you‘ll find the stately building that houses Treetop Paradise.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
2.5 Baths
6 Guests
Just steps away from Harry Truman's "Little White House" you find your dream come true spacious vacation rental home
Daily - Weekly / PoolWasher/DryerGated Community
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