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Sugarloaf Vacation Rentals & Homes - 165 Rentals Available

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165 Vacation rentals

1 / 13

Sugarloaf House

  • 3
  • 6
  • 30 nights min
  • Child friendly
  • Pet friendly

$167.00

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from $167.00 / night

1 / 8

Sugarloaf House

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

$144.00

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from $144.00 / night

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 / 17

Sugarloaf House

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

$170.00

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from $170.00 / night

Your search has been expanded 16.8 miles to include more rentals

1 / 10

Little Torch Key House - 11.4 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 / 18

Ramrod Key House - 9.1 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 / 11

Ramrod Key House - 9.1 miles away

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

$90.00

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from $90.00 / night

1 / 16

Cudjoe Key House - 3.5 miles away

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

$150.00

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from $150.00 / 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

Ramrod Key House - 9.1 miles away

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

$104.00

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from $104.00 / 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 / 17

Little Torch Key House - 10.4 miles away

  • 2
  • 6
  • 30 nights min
  • Child friendly

$114.00

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from $114.00 / night

1 / 10

Ramrod Key House - 9.1 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 / 11

Ramrod Key House - 9.3 miles away

  • 3
  • 8
  • 30 nights min
  • Child friendly
  • Pet friendly

$167.00

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from $167.00 / night

1 / 23

Little Torch Key House - 10.4 miles away

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

$191.00

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from $191.00 / night

1 / 27

Big Pine Key House - 12.8 miles away

  • 5
  • 10
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$197.00

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from $197.00 / night

1 / 17

Summerland Key House - 5.2 miles away

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

$151.00

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from $151.00 / night

1 / 12

Big Pine Key House - 11.4 miles away

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

$109.00

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from $109.00 / 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 / 11

Key West House - 1.4 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$394.00

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from $394.00 / night

1 / 12

Summerland Key House - 6.7 miles away

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

$200.00

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from $200.00 / night

1 / 13

Summerland Key House - 6.7 miles away

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

$217.00

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from $217.00 / night

1 / 13

Ramrod Key House - 9.1 miles away

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

$110.00

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from $110.00 / night

1 / 12

Key West House - 1.2 miles away

  • 2
  • 4
  • 30 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

(1)

1 / 15

Key West Apartment - 16.5 miles away

  • 1
  • 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children

$115.00

Excellent (1 reviews)

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from $115.00 / night

(156)

1 / 28

Key West Apartment - 13.8 miles away

  • 2
  • 5
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 23 minutes

“Accommodations are perfect- easy to access, not too far from the sites and beaches! Building is very quiet even with a rather large pool area...”
- Review left on 02/20/2019

$180.00

Excellent (156 reviews)

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from $180.00 / night

1 / 15

Cudjoe Key House - 4.9 miles away

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

$74.00

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from $74.00 / night

1 / 8

Little Torch Key House - 10.3 miles away

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

$132.00

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from $132.00 / night

1 / 12

Ramrod Key House - 9 miles away

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

$119.00

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from $119.00 / night

1 / 11

Cudjoe Key House - 3.5 miles away

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

$167.00

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from $167.00 / 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

1 / 19

Ramrod Key House - 8.7 miles away

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

$272.00

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from $272.00 / 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 / 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

(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

1 / 34

Key West Penthouse - 16.8 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary

$796.00

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from $796.00 / night

1 / 12

Big Pine Key House - 11.3 miles away

  • 2
  • 4
  • 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 - 5 miles away

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

$110.00

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from $110.00 / night

1 / 19

Summerland Key House - 6.7 miles away

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

$211.00

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from $211.00 / night

1 / 12

Cudjoe Key House - 4.8 miles away

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

$107.00

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from $107.00 / night