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Showing 1-25 of 65 Vacation Rentals

Bahama House

Key West, Florida, United States
$595
1-305-296-6996
house 3 BR 3 BA Sleeps 8

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

Key West, Florida, United States
house 2 BR 2 BA Sleeps 6

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

Casa on Casa

Key West, Florida, United States
$8,500
1-305-296-6996
house 4 BR 3 BA Sleeps 8

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

Key West, Florida, United States
house 2 BR 2 BA Sleeps 6

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

Tropical Dreaming

Key West, Florida, United States
$345
1-305-296-6996
house 2 BR 2 BA Sleeps 6

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

Key West, Florida, United States
house 3 BR 2 BA Sleeps 6

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

Key West, Florida, United States
cottage 2 BR 1 BA Sleeps 4

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

Key West, Florida, United States
house 2 BR 2 BA Sleeps 4

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

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 4

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

Key West, Florida, United States
house 1 BR 2 BA Sleeps 4

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

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 4

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

Key West, Florida, United States
house 4 BR 4 BA Sleeps 14

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

Sunshine on the Rocks

Key West, Florida, United States
$3,500
1-305-296-6996
condo 2 BR 2 BA Sleeps 6

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

Key West, Florida, United States
cottage 1 BR 2 BA Sleeps 4

This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... more

Bogey's Retreat

Key West, Florida, United States
$2,100
1-305-296-6996
townome 2 BR 1 BA Sleeps 6

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

Key West, Florida, United States
house 3 BR 3 BA Sleeps 8

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

Key West, Florida, United States
villa 3 BR 3 BA Sleeps 8

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

Key West, Florida, United States
condo 2 BR 2 BA Sleeps 4

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

Key West, Florida, United States
house 3 BR 4 BA Sleeps 6

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

Key West, Florida, United States
$3,200
1-305-296-6996
house 3 BR 2 BA Sleeps 8

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

Key West, Florida, United States
condo 1 BR 1 BA Sleeps 2

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

Key West, Florida, United States
townome 3 BR 4 BA Sleeps 8

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

Key West, Florida, United States
condo 2 BR 1 BA Sleeps 4

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

Key West, Florida, United States
condo 3 BR 2 BA Sleeps 8

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

Key West, Florida, United States
townome 2 BR 2 BA Sleeps 6

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

Showing 1-25 of 65 Vacation Rentals

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