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Vacation Rentals & House Rentals in Sugarloaf Key

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369 Results

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369 house rentals

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$396

Great rentals within 20 miles that match your search

La Brisa

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$189

Upper Bayview South

Stock Island condo

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$828

Captain's Daughter

Stock Island house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,324

Bayview Retreat

Stock Island townhouse

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,059

Seafarer's Refuge

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,059

Island Chic

Stock Island townhouse

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$794

Eisenhower Retreat

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,059

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$106

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$141

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$269

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

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

Responds fast! avg. 1 hour 45 minutes

Price per night from

$352

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Price per night from

$411

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$295

Old Town, 5 Bdrm Home with Pool

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 42 minutes

Price per night from

$413

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$240

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 35 minutes

Price per night from

$506

Sunshine suit (2/2 apartment)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$295

SEAPORT SUNSETS in Old Town, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$656

The Green House -Sunrise

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$351

3/2 Pool Home on Cudjoe Key. Room for 25-28 foot boat.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$195

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

SEAPORT SUMMIT in Old Town, Key West, FL (Beach-Pool-BBQ)

Key West condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$656

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$133

Key West Hyatt Windward Pointe

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$236

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$159

Palma House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

Treasure Cove

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$471

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$823

Price per night from

$136

Belle Marie

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$311

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$337

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$461

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$183

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$199

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$119

FLORIDA KEYS PARADISE! HEATED SWIMMING POOL

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$295

Viewing 38 of 369
rentals in Sugarloaf Key

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