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Houses Sugarloaf

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140 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

$174

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$227

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$163

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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$181

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

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$163

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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$287

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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$571

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$394

Old Town Treasure, Historic Seaport, Conch House 3 Bedrooms 3.5 Baths, Pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

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$479

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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$888

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$599

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$558

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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$369

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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$306

Old Town *Pink Conch House" with Pool

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 53 minutes

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$296

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$160

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 37 minutes

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Price per night from

$190

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

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$204

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$4,070

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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$332

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms / 1 bathroom / sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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$103

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$183

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

$189

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$133

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Price per night from

$266

Big Pine 2/2 ,Water Views

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 44 minutes

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$148

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

$133

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 48 minutes

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Price per night from

$117

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

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$164

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$279

Sun Kissed

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$115

Breeze Swept

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$221

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$153

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$105

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$231

Blue Marlin

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$163

Palm Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$201

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$95

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