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Houses Sugarloaf

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151 houses

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$173

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$234

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

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$176

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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$178

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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$334

PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage

Sugarloaf house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 49 minutes

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$457

Great rentals within 20 miles that match your search

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

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$575

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.

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$329

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

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$690

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. 1 hour 26 minutes

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$345

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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$134

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$130

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“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 9 minutes

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$2,207

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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$2,068

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

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$1,148

HISTORIC KEY WEST - Turtle House - Sleeps 6

Key West house

2 bedrooms / 1 bathroom / sleeps 6

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$1,493

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

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$1,148

Angelfish Cove

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$159

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$231

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$257

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$161

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

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$126

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$335

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

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$129

Owl's Nest

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$154

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$121

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

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$101

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

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$111

Quiet Waters

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$141

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

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$236

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$161

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$314

Palm Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$208

St. Croix

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$108

Coral House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$184

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$288

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$158

Olivia Place

Key West house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$345

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