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Wireless Internet
Air conditioning
Swimming pool
Private pool

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

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Pets
Pets allowed
Parking
Car not required

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

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront
Waterfront

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81 houses

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Florida Keys at it's best

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$241

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$333

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Sugarloaf house

4 bedrooms
4 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$458

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$204

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Satellite TV, Rental types

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Price per night from

$258

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Satellite TV, Rental types

1 of 2 filters match

Price per night from

$231

Great rentals within 20 miles that match your search

The Mermaids House, Historic Old Town Key West

Key West house

2 bedrooms
1 bathroom

sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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Price per night from

$328

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$622

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

2 bedrooms
1 bathroom

sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

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Price per night from

$134

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$1,491

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$345

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$172

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$340

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

Summerland Key house

5 bedrooms
5 bathrooms

sleeps 10

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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

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Price per night from

$493

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$287

Hogfish Retreat

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$178

Key West Island Vacation

Key West house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$481

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

2 bedrooms
1 bathroom

sleeps 6

Match: Rental types Satellite TV

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Price per night from

$259

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

Match: Rental types Satellite TV

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Price per night from

$775

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Rental types Satellite TV

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Price per night from

$574

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$308

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$482

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

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

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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

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Price per night from

$229

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$379

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$476

Charming House on deep clear canal

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 44 minutes

Match: Rental types Satellite TV

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Price per night from

$201

Tranquility in Paradise - Cudjoe

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Rental types Satellite TV

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Price per night from

$218

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types Satellite TV

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Price per night from

$231

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms
3 bathrooms

sleeps 10

Match: Rental types Satellite TV

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Price per night from

$385

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Rental types Satellite TV

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Price per night from

$224

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$253

Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$240

Sweet Caroline Seaport Floor 2

Key West house

2 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$276

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

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Price per night from

$320

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

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

Match: Rental types Satellite TV

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Price per night from

$801

Palmetto Retreat

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types Satellite TV

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Price per night from

$144

Viewing 38 of 81
rentals in Sugarloaf

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Houses Sugarloaf

Per night

81 houses

Viewing 38 of 81rentals in Sugarloaf

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Viewing 38 of 81
rentals in Sugarloaf