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Sugarloaf Vacation Rentals & Homes - 171 Rentals Available

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171 Vacation rentals

1 / 19

Sugarloaf House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$189.00

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from $189.00 / night

1 / 8

Sugarloaf House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$140.00

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from $140.00 / night

1 / 17

Sugarloaf House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$160.00

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from $160.00 / night

1 / 12

Sugarloaf House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$140.00

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from $140.00 / night

Your search has been expanded 17.1 miles to include more rentals

1 / 17

Summerland Key House - 5.2 miles away

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$201.00

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from $201.00 / night

(70)

Certificate of Excellence

1 / 25

Key West Condo - 13.8 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 58 minutes

Certificate of Excellence

“The Condo had such a beachy feel you knew you were on vacation. It was so clean and had anything you needed. Very nice pool also. The location was great only a 10-minute drive to any main attraction. Would highly recommend this unit as we will...”
- Review left on 12/10/2018

$228.00

Excellent (70 reviews)

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from $228.00 / night

1 / 12

Key West House - 1.2 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

1 / 9

Key West House - 1.2 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$343.00

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from $343.00 / night

1 / 8

Key West House - 1.1 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$536.00

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from $536.00 / night

(4)

1 / 11

Key West Guest house - 1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$393.00

Excellent (4 reviews)

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from $393.00 / night

(2)

1 / 29

Cudjoe Key House - 4.8 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$229.00

Very Good (2 reviews)

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from $229.00 / night

(17)

1 / 10

Key West Townhouse - 17.1 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$258.00

Excellent (17 reviews)

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from $258.00 / night

1 / 14

Cudjoe Key House - 5 miles away

  • 2
  • 6
  • 28 nights min
  • Child friendly
  • Pet friendly

$115.00

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from $115.00 / night

1 / 19

Ramrod Key House - 8.7 miles away

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$255.00

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from $255.00 / night

1 / 17

Key West House - 6.9 miles away

  • 2
  • 4
  • 28 nights min
  • Child friendly

$150.00

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from $150.00 / night

1 / 12

Cudjoe Key House - 4.8 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$100.00

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from $100.00 / night

1 / 18

Summerland Key House - 9 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$100.00

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from $100.00 / night

1 / 18

Little Torch Key House - 11.4 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$97.00

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from $97.00 / night

1 / 15

Ramrod Key House - 9.1 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

$140.00

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from $140.00 / night

1 / 10

Little Torch Key House - 11.4 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$67.00

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from $67.00 / night

1 / 11

Cudjoe Key House - 4.7 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$134.00

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from $134.00 / night

1 / 16

Cudjoe Key House - 4.9 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$87.00

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from $87.00 / night

(1)

1 / 18

Little Torch Key House - 10.3 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$120.00

Excellent (1 reviews)

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from $120.00 / night

1 / 18

Summerland Key House - 6.8 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$168.00

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from $168.00 / night

1 / 19

Cudjoe Key House - 4.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$134.00

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from $134.00 / night

1 / 8

Little Torch Key House - 10.3 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$125.00

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from $125.00 / night

1 / 12

Big Pine Key House - 11.3 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$133.00

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from $133.00 / night

1 / 15

Big Pine Key House - 13.2 miles away

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$87.00

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from $87.00 / night

1 / 22

Summerland Key House - 6.8 miles away

  • 4
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$200.00

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from $200.00 / night

1 / 16

Big Pine Key House - 13.2 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$94.00

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from $94.00 / night

1 / 12

Cudjoe Key House - 3.5 miles away

  • 3
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$120.00

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from $120.00 / night

1 / 12

Big Pine Key House - 11.4 miles away

  • 2
  • 4
  • 31 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$105.00

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from $105.00 / night

1 / 17

Summerland Key House - 6.4 miles away

  • 3
  • 8
  • 28 nights min
  • Child friendly

$268.00

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from $268.00 / night

1 / 15

Ramrod Key House - 9 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$120.00

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from $120.00 / night

1 / 19

Ramrod Key House - 9.1 miles away

  • 4
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$230.00

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from $230.00 / night

1 / 16

Little Torch Key House - 11.4 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$140.00

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from $140.00 / night

1 / 14

Cudjoe Key House - 4.6 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$100.00

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from $100.00 / night

1 / 16

Big Pine Key House - 13.3 miles away

  • 4
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$200.00

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from $200.00 / night

(1)

1 / 15

Ramrod Key House - 9.2 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$180.00

Average (1 reviews)

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from $180.00 / night

1 / 16

Little Torch Key House - 11.4 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$120.00

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from $120.00 / night