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339 houses

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Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$185

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$212

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$160

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$178

Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$347

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$159

Great rentals within 20 miles that match your search

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$147

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$172

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 35 minutes

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Price per night from

$527

Palma House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

Treasure Cove

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$491

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$208

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$212

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$528

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 45 minutes

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Price per night from

$175

Vacation house for a family for oct

Key West house

3 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$615

Bahama House - A++ Location with private pool/parking - walk to everything!

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$830

Blue Heron

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$113

Cudjoe - Tranquility in Paradise

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$192

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$172

Cudjoe Ocean Shores

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Pink House

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$180

The Mermaids House, Historic Old Town Key West

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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Price per night from

$308