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
4 Guests
Looking for the perfect home away from home? No need to look any further!
No shoes needed at “A Barefoot Retreat” in the lovely Shipyard section of the historic Truman Annex private community.
Daily - Weekly / PoolWasher/DryerGated Community
2 Bedrooms
2 Baths
4 Guests
Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining.
One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.
30 Day RentalPoolGrillWasher/DryerPets Allowed
2 Bedrooms
1.5 Baths
4 Guests
Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table.
30 Day RentalGrillWasher/Dryer
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
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 Baths
4 Guests
Leeward Isle Key West Retreat – Location is everything! A hidden gem in the heart of Old Town Key West.
Daily - Weekly / PoolWasher/DryerGated Community
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
1 Bedroom
1 Bath
4 Guests
Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking.
30 Day RentalPoolGrillWasher/DryerGated CommunityPets Allowed
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
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
1.5 Baths
4 Guests
For the golfer in the family and for those who just want an idyllic vacation spot, Coral Breeze is the logical choice!
30 Day RentalPoolGrillWasher/DryerGated Community
1 Bedroom
2 Baths
2 Guests
Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street.
30 Day RentalGrillWasher/Dryer
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