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Vacation Rentals & House Rentals in Sugarloaf Key

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319 Results

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319 house rentals

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$385

Great rentals within 20 miles that match your search

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$557

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 45 minutes

Price per night from

$185

A LITTLE PIECE OF THE CARIBBEAN IN THE U. S.

Key West condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$344

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$323

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$384

Old Town Treasure, Historic Seaport, Conch House 3 Bedrooms 3.5 Baths, Pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$467

Term Charterboat w/ FREE Sunset Cruise

Key West houseboat

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$388

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

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$866

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$584

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$544

Old Town, 5 Bdrm Home with Private Pool in Gated Backyard

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

Price per night from

$360

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.

Price per night from

$299

Grouper Therapy

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$156

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$277

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$135

Venture Out 128

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$222

Coconut Cay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$166

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$112

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$203

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$151

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$123

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$184

Casa Rosa

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$125

Paradise Bay

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$122

Cudjoe Cottage

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$132

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$156

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$142

St. Croix

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$101

Bahia Azul

Ramrod Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$256

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$111

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$156

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$204

Palm Harbor

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$145

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$111

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$94

Viewing 38 of 319
rentals in Sugarloaf Key

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