Sugarloaf Houses | FlipKey Vacation Rentals

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$188

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$172

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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$170

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$143

Sugarloaf Sunset

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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$167

Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 9

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$323

Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$149

Key West Wabi Sabi ~ Weekly Rental

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

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$751

Poinciana House

Key West house

1 bedroom / 2 bathrooms / sleeps 4

“Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels to suntan lotion. There was nothing we needed to bring except our clothes & food. I would definitely stay here again.

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$334

Heavenly Hideout at Rainbow's End ~ Weekly Rental

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

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$1,028

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$124

Island Oasis Garden Home ~ Weekly Rental

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$253

Bernie's Bungalow

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$117

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

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$587

Private and Immaculate 2 Bedroom Home with Private Fenced Yard

Key West house

2 bedrooms / 1 bathroom / sleeps 4

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$142

Angelfish Cove

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$127

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

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$206

Blackbeard's Treasure - MONTHLY Rental (30 night min.)

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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$178

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

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$669

Venture Out 128

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$220

Kemp House

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

“Perfect little resort” The Kemp House was warm and inviting after Our team of ladies finished our Ultramarathon relay. The pool and courtyard were the perfect place to unwind. Plenty of room for everyone! Perfect location a block from the seaport and two more to Duval. Air conditioner wasn't blowing cold air in the one room but contacted Historic Hideaways and they sent someone within a half hour to fix/replace it! It's a perfect little private resort...We will definitely be back!

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$509

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$193

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!!!!

Responds fast! avg. 2 hours 24 minutes

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$103

Classic Key West Estate ~ Weekly Rental

Key West house

7 bedrooms / 6 bathrooms / sleeps 14

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$1,542

Island Elegance ~ Monthly Rental

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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$309

Private Key West Sunset ~ Weekly Rental

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$896

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$156

Yellow weekly vacation home, great location. Heated private pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$396

Tree House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$104

The Meadows House

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“The Meadows Home- wow !!!” Tim, Thank you so much for your help in booking The Meadows Home. I have to say when I was booking the home, I was a little afraid of the pictures I saw on line. The pictures do not do justice to show the beauty of the home and the pool... Wow!!! My in-laws went back home to Poland toady they couldn't stop talking about what a great time they had in Key West and what a wonderful time we had in the house, swimming and drink by the pool. I really hope my family and I can return and visit the home again. Best Wishes, The Zatek Family

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$328

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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$575

Pink House

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$168

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$162

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$1,811