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Houses Sugarloaf

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152 houses

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 32 minutes

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Price per night from

$172

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$224

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$169

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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$177

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$286

Great rentals within 20 miles that match your search

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

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$562

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$388

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$873

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$589

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$548

Old Town, 5 Bdrm Home with Private Pool in Gated Backyard

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$363

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

$301

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$4,001

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$326

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

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Price per night from

$186

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$131

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Price per night from

$262

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$131

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$161

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$228

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$93

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$123

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$114

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$118

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$138

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$164

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$194

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$298

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$146

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$119

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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Price per night from

$161

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$196

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$113

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$120

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$447

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$130

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$430

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houses in Sugarloaf

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