Houses Sugarloaf

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177 houses

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$4,017

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Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$316

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$976

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Price per night from

$263

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$917

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$523

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$346

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$913

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Price per night from

$913

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$526

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$668

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$656

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$472

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$445

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$622

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

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

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Price per night from

$574

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

$329

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$622

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

$344

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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Price per night from

$134

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

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Price per night from

$2,124

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$1,491

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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Price per night from

$2,065

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$1,147

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$204

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$198

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$268

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$258

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$318

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$151

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$141

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$278

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$148

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