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Houses Summerland Key

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100 houses

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

$556

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$224

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$478

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$455

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

$767

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$163

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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$297

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$230

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$130

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$287

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$1,718

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$517

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

$161

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$244

Reel Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$292

New Listing!!! BIRDS OF PARADISE - Amazing Sunsets, Open Water Views, Dockage &

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$179

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$267

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

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$304

New Listing! KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Y

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

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$179

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$197

BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 13

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Price per night from

$174

THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 12

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Price per night from

$174

ENDLESS SUMMER COTTAGE - Your Tropical Island Escape, Open Water Views, Amazing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$179

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$201

THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

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$144

Great rentals within 20 miles that match your search

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 16 minutes

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Price per night from

$161

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$104

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$114

Manatee Bay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$119

Margarita Villa

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$154

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$243

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$178

Paradise Bay

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$126

Pirates Pointe

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$146

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$517

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$118

Bahia Azul

Ramrod Key house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$258

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$114

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