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Sugarloaf Rentals

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305 Results

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Price: high to low

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305 Houses

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$178

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 32 minutes

Price per night from

$172

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$225

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$170

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

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

Price per night from

$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

Price per night from

$564

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$389

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

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$876

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$591

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$551

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

Price per night from

$364

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.

Price per night from

$302

Private, heated pool. Private yard.

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

Price per night from

$2,995

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$4,016

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$328

Luxury 3BD/3B Penthouse Condo at Galleon Resort, Old Key West

Key West condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 28 minutes

Price per night from

$919

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

Price per night from

$583

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$187

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

key west tree house

Key West apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Price per night from

$263

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

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$162

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 38 minutes

Price per night from

$100

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$276

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$228

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$94

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$123

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$118

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$194

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$299

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$146

Viewing 38 of 305
rentals in Sugarloaf

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