Sugarloaf Rentals

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253 Houses

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$241

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$257

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$203

South Point Shores

Sugarloaf house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

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Price per night from

$332

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$458

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$114

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

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

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Price per night from

$487

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$916

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$317

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$235

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$150

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$188

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$197

Quiet Waters

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$160

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$147

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$117

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$217

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$143

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$413

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$267

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$277

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$140

St. Croix

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$120

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$163

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

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$107

Pirates Pointe

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$173

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$344

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$160

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Beautiful Home Located In Quiet neighborhood

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$339

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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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Price per night from

$328

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

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Price per night from

$1,300

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.

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Price per night from

$487

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$343

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rentals in Sugarloaf

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