Below you will find a list of all of our Key West, Florida vacation rentals, a variety of properties listed alphabetically, along with photo and brief description. You can view additional pictures and detailed information about the property by clicking on the property name. Have fun browsing!!!
Don't forget to check out our Key West Vacation Deals too, we've got great specials available! And remember, book direct & save big!
AMELIA HOME: A private Key West vacation home that is only four blocks from one of our most popular beaches on the Atlantic Ocean and one block from all the Duval Street entertainment. This 2 bedroom 2.5 bath single family home with private pool is located in one of the most interesting neighborhoods in the historic district of Old Town Key West.
CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome. Located in Truman Annex, a secluded gated community within Old Town Key West, everything you want to do is within easy walking distance -- tourist attractions, beach, bars, restaurants.
BOGEY'S RETREAT (monthly rental): Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy everything Key West has to offer in a relaxing environment. New to the rental market and updated from top to bottom with supreme comfort in mind.
PAPAYA PLACE: This spacious 2 bedroom 2 bath condominium at 1800 Atlantic offers a wonderful relaxing view of the nature preserve next door and the ocean beyond. Well-equipped with all the modern conveniences. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you to be lost in the tropical breezes.
PARROT PERCH: Located in the gated community known as Truman Annex, you are in walking distance of all the activities to experience while visiting our island paradise. This 2nd floor condo with 2 bedrooms 2 baths and sleeper sofa offers a welcome respite in a great location and a great value for a great vacation.
LAVENDER JUNGLE: Beautiful 2 bedroom 1 bath downstairs Shipyard condo in Truman Annex with back deck that opens to the entrance of Fort Zachary Taylor State Park, one of the nicest beaches on the island. Truman Annex, a secure gated community within Old Town Key West, is within walking distance of all the favorite hotspots on the island.
THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.
A PLACE IN PARADISE: You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in prestigious Truman Annex. Spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora that exemplifies the best of Key West. Walk two blocks to all that Duval Street has to offer.
SPA ON DUVAL: A tropical 2-story, 2 bedroom 2.5bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, specialty shops and the action of Duval Street. Catch the rays on the pool deck or soothe tired muscles in the private jacuzzi on your own deck. Spa On Duval is truly a Key West experience to enjoy.
ALLURING PORCHES: A beautiful 2 bedroom 3 bath townhome with den, offering 3 private bedrooms with baths ensuite. Enjoy the abundant french doors that open the entire downstairs to the outdoors and give this home easy open air living. Located in the Porter Lane section of Truman Annex in walking distance of all there is to enjoy in Old Town.
BOWE CONCH HOUSE: The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Ethel Bowe-Thomas purchased the house in the 1930's, raised her family there, planted the massive poinciana tree that offers shade in the backyard, and now her family wants to share it with you. A unique opportunity to experience life in Key West through the eyes of a Conch.
TRUMAN'S HIDEAWAY: 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. Located in the exclusive Harbour Place complex, it has all the comforts of home and more. Conveniently located in Truman Annex, within walking distance of all Key West activities, you'll be tempted to return again and again.
VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!
A SUITE PARADISE (monthly rental) : This lovely 2 bedroom 2 bath home with den is truly a tropical hideaway tucked away in a secluded Key West neighborhood, yet minutes from all the Duval Street entertainment and Historic Seaport. You can relax and be pampered in a superbly appointed and decorated private home that has every amenity you could desire.