Key West, FL Vacation Rentals
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Showing 1-25 of 65 Vacation Rentals
Totally gorgeous, Bahama House is conveniently located on a quiet street in the heart of Old Town Key West around the corner from the fabulous shops,... more
Duval Breeze
Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street in Old Town Key West and a few blocks from the... more
So simple yet elegant, intimate yet spacious, Casa on Casa offers a unique Key West experience that will linger in your memory for years to come. As... more
Southard Queen Conch Suite
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation... more
A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while... more
Coconut Cabana
An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of... more
Mango Managerie
Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just... more
President's Walk
President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its... more
Waterfront Two-Bedroom Suite
Upgrade to luxury with a master king room, second queen room, living room, and water view balcony. Breathe the salt air from a beautiful two-bedroom... more
Tropical Serenity
An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bungalow has been completely... more
Beach Club #104
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This 2 bedroom 2 bath unit has a wonderful... more
Southard Street - Queen Conch
On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation... more
This stunning townhome has spectacular waterfront views of the bay with an ideal location on a secluded peninsula. Sunshine On The Rocks is the... more
Ann Street Cottage
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... more
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... more
Villa Paradiso
This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three... more
Waterfront Three-Bedroom Villa
Discover our waterfront double queen guest room with two queen beds, a white sand terrace, and water view porch. Step off your porch and feel the sand... more
Beach House Condo
Beach House Condo has the perfect back deck to sip a cafe con leche in the morning or read a book in the afternoon. The property has an open floor... more
Duval Roost
This sanctuary is located one half block from Duval Street in the heart of Old Town tucked away on a private lane. Enter the property through a secure... more
Flagler Station is a recently remodeled, refurbished and re-furnished rental that features a spacious living room and dining area, allowing plenty of... more
Casa Atlantica One Bedroom
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Filled... more
Paradise Harbor Retreat
Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Keys... more
Shipyard Treasure
Decorated in casual contemporary style, Shipyard Treasure is centrally located in the Truman Annex, as well as within quick walking distance to all... more
Beach Club #108
Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This elegant 3 bedroom/ 2 bath unit... more
Duval Square Castaway
In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and... more