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Sugarloaf Rentals

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age 0-16
574 Results

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Price: high to low

Number of reviews

574 Houses

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$180

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$175

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$217

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$163

Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$328

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

$186

Upper Bayview South

Stock Island condo

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$816

Captain's Daughter

Stock Island house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,305

Bayview Retreat

Stock Island townhouse

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,044

Seafarer's Refuge

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,044

Island Chic

Stock Island townhouse

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$783

Eisenhower Retreat

Stock Island house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,044

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$104

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$139

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$265

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

$162

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

$346

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

$405

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

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

$407

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$237

"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

$498

Sunshine suit (2/2 apartment)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

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

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$647

The Green House -Sunrise

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$346

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

$192

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$115

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

Key West condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$647

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$132

Key West Hyatt Windward Pointe

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$232

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$157

Palma House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Responds fast! avg. 3 hours 51 minutes

Price per night from

$290

Treasure Cove

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$465

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$811

Price per night from

$134

Belle Marie

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$307

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$332

Viewing 38 of 574
rentals in Sugarloaf

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