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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
Fax machine
Private outdoor pool (unheated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Pool or snooker table
Private outdoor pool (heated)
Trampoline
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
Swing set or jungle gym
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
Elevator access
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
Waterfront
Beach or lakeside relaxation
Golf within 30mins drive
Lakefront

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127 houses

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Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$257

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$203

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$230

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

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

$332

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$114

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$317

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$267

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$287

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$197

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$140

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$235

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$147

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$143

Margarita Villa

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$188

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$150

Our Island Thing

Big Pine Key house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$277

Quiet Waters

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$160

Pirate's Cove

Cudjoe Key house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$117

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$120

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$413

Coral House

Ramrod Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$217

Big Torch Retreat

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$163

Pirates Pointe

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$173

Olivia Place

Key West house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$344

Island Chalet

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$160

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$172

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

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$790

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$621

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms
3 bathrooms

sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$343

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

5 bedrooms
6 bathrooms

sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

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Price per night from

$2,119

HISTORIC KEY WEST - Main House - Sleeps 8

Key West house

4 bedrooms
2 bathrooms

sleeps 8

“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!

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Price per night from

$2,060