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Sugarloaf Rentals

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237 Results

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237 Houses

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$185

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

Price per night from

$173

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$222

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$161

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$167

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

$288

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

$561

A LITTLE PIECE OF THE CARIBBEAN IN THE U. S.

Key West condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$347

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

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$326

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$387

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

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$471

Term Charterboat w/ FREE Sunset Cruise

Key West houseboat

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$391

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

$872

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$588

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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

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.

Price per night from

$301

Grouper Therapy

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$157

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$279

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$136

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$205

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$123

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$143

St. Croix

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$102

Sunny Lei

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$155

Blue Marlin

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Old Town *Pink Conch House" with Pool

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 53 minutes

Price per night from

$291

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$124

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$120

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$157

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 37 minutes

Price per night from

$187

Eleanor's Place in Key West Old Town - Dogs Ok

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

Price per night from

$127

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

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Price per night from

$200

One-bedroom suite in the heart of Old Key West

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 22 minutes

Price per night from

$216

Palm Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$195

Sun Kissed

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$112

Viewing 38 of 237
rentals in Sugarloaf

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