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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
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Washing machine
Jacuzzi or hot tub
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Internet access
DVD player
Grill
Cot available
Sea view
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Dishwasher
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Pool or snooker table
Table tennis
Games room
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Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
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Stove
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Boat available
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Towels provided
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Trampoline
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Housekeeping Included

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Pets
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Parking
Car not required

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Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
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Horse riding
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Waterfront
Golf within 30mins drive
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267 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

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

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

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$1,141

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

Great rentals within 20 miles that match your search

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

4 bedrooms
2 bathrooms

sleeps 8

Price per night from

$408

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$971

Historic Carriage House

Key West cottage

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$229

Coconuts on the Water

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$205

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

Price per night from

$514

All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter

Stock Island yacht

1 bedroom
1 bathroom

sleeps 6

Price per night from

$262

Lobster Lagoon

Stock Island house

4 bedrooms
4 bathrooms

sleeps 9

Price per night from

$971

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$327

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 7

Price per night from

$228

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$744

Moveable Feast

Key West house

4 bedrooms
5 bathrooms

sleeps 10

Price per night from

$430

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$471

Coconut Mallory Resort and Marina

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$346

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$525

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

A Change in Latitudes - TRUMAN ANNEX

Key West condo

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$172

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

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Key West villa

6 bedrooms
7 bathrooms

sleeps 16

Price per night from

$2,004

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

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$203

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$257

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$317

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

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$197

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

Price per night from

$147

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$267

Viewing 38 of 267
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

267 house rentals

Viewing 38 of 267rentals in Sugarloaf Key

Also consider

Viewing 38 of 267
rentals in Sugarloaf Key