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Wireless Internet
Air conditioning
Swimming pool
Private pool

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Private indoor pool
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Washing machine
Jacuzzi or hot tub
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Internet access
DVD player
Grill
Cot available
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Pool or snooker table
Table tennis
Games room
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Private outdoor pool (unheated)
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Boat available
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Housekeeping Included

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Pets
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Parking
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Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
Skiing – property near ski resort
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Nightlife
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Horse riding
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Waterfront
Golf within 30mins drive
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266 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

$1,140

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

Great rentals within 20 miles that match your search

Key West House

Key West house

2 bedrooms
3 bathrooms

sleeps 6

Price per night from

$689

Pirates Paradise

Cudjoe Key house

3 bedrooms
4 bathrooms

sleeps 6

Price per night from

$434

Blackbeard's Bounty

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$234

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

2 bedrooms
1 bathroom

sleeps 5

Price per night from

$345

Blackbeard's Escape

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$359

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$287

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

4 bedrooms
2 bathrooms

sleeps 8

Price per night from

$410

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 10

Price per night from

$775

Noah, Family Ocean Paradise

Key West house

3 bedrooms
4 bathrooms

sleeps 8

Price per night from

$1,337

Into the Mystic

Summerland Key house

6 bedrooms
6 bathrooms

sleeps 12

Price per night from

$466

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 24 minutes

Price per night from

$402

Key West Bayfront Paradise - House and Private Pool! Steps from shops and food

Key West house

4 bedrooms
3 bathrooms

sleeps 8

Price per night from

$614

Lobster Lagoon

Stock Island house

4 bedrooms
4 bathrooms

sleeps 9

Price per night from

$975

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

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$975

Historic Carriage House

Key West cottage

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$230

Coconuts on the Water

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$206

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

$517

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

$263

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$743

Island Suite @ KW Vacation

Key West apartment

1 bedroom
1 bathroom

sleeps 4

Price per night from

$401

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

4 bedrooms
2 bathrooms

sleeps 10

Price per night from

$757

Waterfront Haven House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
1 bathroom

sleeps 8

Price per night from

$457

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 7

Price per night from

$228

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$667

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$622

Moveable Feast

Key West house

4 bedrooms
5 bathrooms

sleeps 10

Price per night from

$430

Sharkys Island Paradise

Big Pine Key house

5 bedrooms
3 bathrooms

sleeps 12

Price per night from

$258

Living On the Hook in Key West Harbour

Key West houseboat

3 bedrooms
2 bathrooms

sleeps 2

Price per night from

$441

Viewing 38 of 266
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

266 house rentals

Viewing 38 of 266rentals in Sugarloaf Key

Also consider

Viewing 38 of 266
rentals in Sugarloaf Key