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127 houses

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Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$464

Gone Fishing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$225

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$200

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$399

Mermaid's Tale

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$192

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 9 minutes

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Price per night from

$1,033

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$451

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$814

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$142

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$278

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$210

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$108

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$259

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$1,256

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

$241

30% off now till March!!! 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

$170

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$229

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$180

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$366

Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 9 minutes

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Price per night from

$371

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$268

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

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Price per night from

$264

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$175

Bright, spacious home with private pool, internet, private washer/dryer, & loft!

Summerland Key house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$1,185

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$189

Villa and guest house with private pool, central AC, internet, and washer/dryer

Summerland Key house

6 bedrooms / 5 bathrooms / sleeps 16

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Price per night from

$1,692

Great rentals within 20 miles that match your search

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$146

Palma House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$160

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$206

Margarita Villa

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

Responds fast! avg. 45 minutes

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Price per night from

$174

Blue Heron

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$112

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$171

Cudjoe Ocean Shores

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$155

Cudjoe Cottage

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$136

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$209

Captivating Cudjoe Key Waterfront Retreat

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$159

Viewing 38 of 127
houses in Summerland Key

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COVID-19 Update

Houses Summerland Key

Per night

127 houses

Viewing 38 of 127houses in Summerland Key

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Viewing 38 of 127
houses in Summerland Key