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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
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Freezer
Staffed property
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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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129 house rentals

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Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Match: Ceiling Fans

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Price per night from

$5,720

Great rentals within 20 miles that match your search

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms
5 bathrooms

sleeps 10

Match: Ceiling Fans

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Price per night from

$766

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

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Price per night from

$493

Key West Island Vacation

Key West house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 8 minutes

Match: Ceiling Fans

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Price per night from

$481

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

Match: Ceiling Fans

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Price per night from

$775

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

2 bedrooms
1 bathroom

sleeps 4

Match: Ceiling Fans

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Price per night from

$342

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

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Price per night from

$912

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

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Price per night from

$210

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

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Price per night from

$229

SEAPORT PANORAMA at Galleon Resort (Beach-Pool & Hot Tub-BBQ-55” TV-Jacuzzi)

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

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Price per night from

$912

One-bedroom time share suite in the heart of Old Key West

Key West condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 26 minutes

Match: Ceiling Fans

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Price per night from

$339

Coconut Cay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

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Price per night from

$208

Hawkins Heaven

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

All filters match

Price per night from

$178

Private, heated pool. Private yard.

Key West condo

1 bedroom
1 bathroom

sleeps 2

Match: Ceiling Fans

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Price per night from

$172

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Ceiling Fans

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Price per night from

$379

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Ceiling Fans

All filters match

Price per night from

$448

Buccaneer Boathouse

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

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Price per night from

$141

Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

Key West condo

1 bedroom
1 bathroom

sleeps 2

Match: Ceiling Fans

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Price per night from

$155

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Ceiling Fans

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Price per night from

$259

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

All filters match

Price per night from

$231

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

All filters match

Price per night from

$184

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Ceiling Fans

All filters match

Price per night from

$174

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

All filters match

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: Ceiling Fans

All filters match

Price per night from

$224

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Ceiling Fans

All filters match

Price per night from

$234

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Ceiling Fans

All filters match

Price per night from

$253

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms
4 bathrooms

sleeps 8

Match: Ceiling Fans

All filters match

Price per night from

$316

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

Match: Ceiling Fans

All filters match

Price per night from

$384

Grouper Therapy

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

All filters match

Price per night from

$214

Sun Kissed

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

All filters match

Price per night from

$158

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

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

Match: Ceiling Fans

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Price per night from

$801

Key West House

Key West house

2 bedrooms
3 bathrooms

sleeps 6

Match: Ceiling Fans

All filters match

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: Ceiling Fans

All filters match

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

Match: Ceiling Fans

All filters match

Price per night from

$775

Noah, Family Ocean Paradise

Key West house

3 bedrooms
4 bathrooms

sleeps 8

Match: Ceiling Fans

All filters match

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: Ceiling Fans

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Price per night from

$402

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

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Ceiling Fans

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Price per night from

$975

Historic Carriage House

Key West cottage

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Match: Ceiling Fans

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Price per night from

$230

Viewing 38 of 129
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

129 house rentals

Viewing 38 of 129rentals in Sugarloaf Key

Also consider

Viewing 38 of 129
rentals in Sugarloaf Key