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Air conditioning
Swimming pool
Private pool

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Private indoor pool
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Jacuzzi or hot tub
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Cot available
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Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
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272 house rentals

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Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms
3 bathrooms

sleeps 10

Price per night from

$384

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

4 bedrooms
4 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Price per night from

$5,720

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

4 bedrooms
4 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V

Sugarloaf Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$1,140

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

Price per night from

$320

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Sugarloaf Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Date Palm Destination: Charming 3BR Canal Front Home in Sugarloaf, Dockage & Dog

Sugarloaf Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$177

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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

Price per night from

$161

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$487

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms
1 bathroom

sleeps 6

Price per night from

$916

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$257

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$197

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$287

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$140

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$203

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

Price per night from

$147

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

Price per night from

$235

Our Island Thing

Big Pine Key house

4 bedrooms
2 bathrooms

sleeps 8

Price per night from

$277

Quiet Waters

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$160

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$317

Pirate's Cove

Cudjoe Key house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$117

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$267

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$143

Margarita Villa

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$188

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$150

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$230

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$413

Coral House

Ramrod Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$217

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$120

Big Torch Retreat

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$163

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 48 minutes

Price per night from

$107

Pirates Pointe

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$173

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

Price per night from

$344

Viewing 38 of 272
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

272 house rentals

Viewing 38 of 272rentals in Sugarloaf Key

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Viewing 38 of 272
rentals in Sugarloaf Key