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125 houses

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Blue weekly vacation rental, great view. Heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$393

Gone Fishing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$211

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$168

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$217

NEW LISTING! Modern, waterfront home w/ a private pool, boat dock, & patio

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 50 minutes

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Price per night from

$866

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$100

Another Day In Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$268

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

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Price per night from

$286

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$686

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$447

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$120

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$200

NEW LISTING! Incredible oceanfront home on large lot w/bar, dock & amazing views

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 13

Responds fast! avg. 2 hours 47 minutes

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Price per night from

$826

Direct Atlantic Ocean front private boat ramp dock

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$189

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

$764

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$421

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$267

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$200

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$152

Great rentals within 20 miles that match your search

St. Croix

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$90

Blue Marlin

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$133

Atlantis Dream Escape

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$326

Bahia Azul

Ramrod Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$230

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$187

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$196

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$286

Blue Tranquility

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$167

Sunset Bay (weekly rental)

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$271

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. 2 hours 27 minutes

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Price per night from

$1,796