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Sugarloaf Vacation Rentals & Homes - 170 Rentals Available

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170 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

$144.00

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from $144.00 / 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

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 / 17

Summerland Key House - 5.2 miles away

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

$134.00

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from $134.00 / night

1 / 12

Key West House - 1.2 miles away

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

$466.00

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from $466.00 / night

(3)

1 / 28

Key West Villa - 16.8 miles away

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly...”
- Review left on 09/08/2016

$1,432.00

Excellent (3 reviews)

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from $1,432.00 / 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

1 / 26

Key West House - 1 miles away

  • 5
  • 10
  • 28 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$743.00

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from $743.00 / night

(20)

1 / 22

Key West B and B - 16.7 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$900.00

Excellent (20 reviews)

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from $900.00 / 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

1 / 28

Key West House - 16.8 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$682.00

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from $682.00 / 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)

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

1 / 13

Cudjoe Key House - 4.3 miles away

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

$196.00

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from $196.00 / 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 / 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 / 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 / 24

Summerland Key House - 6.6 miles away

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

$267.00

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from $267.00 / 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 / 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 / 19

Cudjoe Key House - 4.7 miles away

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

$95.00

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from $95.00 / night

1 / 15

Little Torch Key House - 10.5 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 / 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 / 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 / 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 / 14

Summerland Key House - 6.8 miles away

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

$120.00

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from $120.00 / night

1 / 18

Little Torch Key House - 11.4 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 / 16

Little Torch Key House - 11.6 miles away

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

$107.00

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from $107.00 / 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 / 18

Cudjoe Key House - 3.5 miles away

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

$187.00

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from $187.00 / night

1 / 12

Cudjoe Key House - 5 miles away

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

$97.00

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from $97.00 / night

1 / 23

Little Torch Key House - 10.4 miles away

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

$190.00

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from $190.00 / 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 / 18

Little Torch Key House - 11.6 miles away

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

$100.00

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from $100.00 / 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 / 12

Cudjoe Key House - 3.5 miles away

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

$124.00

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from $124.00 / 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 / 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