Sugarloaf Rentals

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177 Houses

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$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

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

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

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$321

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

$573

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$790

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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$621

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 2 hours 26 minutes

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$602

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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$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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$343

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$107

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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$133

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

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$434

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

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$464

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

$2,119

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

$2,060

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 58 minutes

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$320

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Price per night from

$2,004

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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

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$197

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$267

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$317

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$150

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

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$277

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$147

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$143

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$188

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

Quiet Waters

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$160

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$217

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$413

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$163

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

Viewing 38 of 177
rentals in Sugarloaf

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