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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
Grill
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Games room
Table tennis
Pool or snooker table
Fax machine
Shared outdoor pool (unheated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Video player
Climbing frame
Boat available
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Staffed property
Microwave
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
Water sports
Horse riding
Fishing
Golf within 30mins drive
Waterfront
Lakefront

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171 house rentals

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Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Match: Linen provided

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Price per night from

$5,720

Great rentals within 20 miles that match your search

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Linen provided

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Price per night from

$174

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$171

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Linen provided

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Price per night from

$224

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Linen provided

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Price per night from

$234

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Linen provided

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Price per night from

$231

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$184

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

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Price per night from

$801

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$4,016

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

Match: Linen provided

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Price per night from

$384

Grouper Therapy

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$214

Sun Kissed

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$158

Key West House

Key West house

2 bedrooms
3 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$689

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

Key West house

2 bedrooms
1 bathroom

sleeps 5

Match: Linen provided

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Price per night from

$345

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

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$775

Noah, Family Ocean Paradise

Key West house

3 bedrooms
4 bathrooms

sleeps 8

Match: Linen provided

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Price per night from

$1,337

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

Match: Linen provided

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Price per night from

$402

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Linen provided

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Price per night from

$701

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

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$976

Historic Carriage House

Key West cottage

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

Match: Linen provided

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Price per night from

$230

Coconuts on the Water

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

Match: Linen provided

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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

Match: Linen provided

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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

Match: Linen provided

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Price per night from

$263

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Linen provided

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Price per night from

$743

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$328

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

4 bedrooms
2 bathrooms

sleeps 10

Match: Linen provided

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Price per night from

$757

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$654

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$471

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$622

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$484

Hyatt Windward Pointe

Stock Island apartment

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$525

Walk to Duval and Mallory Square!

Stock Island condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$523

Moveable Feast

Key West house

4 bedrooms
5 bathrooms

sleeps 10

Match: Linen provided

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Price per night from

$430

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 46 minutes

Match: Linen provided

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Price per night from

$384

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

Match: Linen provided

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Price per night from

$395

A Spring Break vacation paradise! And a short walk to the best of Key West!

Key West condo

3 bedrooms
3 bathrooms

sleeps 8

Match: Linen provided

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Price per night from

$344

Sharkys Island Paradise

Big Pine Key house

5 bedrooms
3 bathrooms

sleeps 12

Match: Linen provided

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Price per night from

$258

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 3 hours 46 minutes

Match: Linen provided

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Price per night from

$384

Viewing 38 of 171
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

171 house rentals

Viewing 38 of 171rentals in Sugarloaf Key

Also consider

Viewing 38 of 171
rentals in Sugarloaf Key