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Summerland Key Rentals

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age 0-16
131 Results

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Price: high to low

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131 Houses

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

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$466

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$197

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$282

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$472

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$139

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$435

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

Price per night from

$255

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$861

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$203

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$280

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$327

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$230

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

Price per night from

$1,718

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$111

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$158

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 37 minutes

Price per night from

$184

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$364

New Listing! Summerland Canal-Front Escape w/ Private Pool & Boat Basin

Summerland Key house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$118

Caribbean House

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$89

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$275

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$271

New Listing!!! Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Docka

Summerland Key house

6 bedrooms / 8 bathrooms / sleeps 14

Price per night from

$3,435

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$172

Blue Fish Point - Luxurious Private Boating Oasis With Amazing Sunsets, Dog Frie

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 10

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

Price per night from

$174

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$182

The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front Home, Great Doc

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

Great rentals within 20 miles that match your search

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 45 minutes

Price per night from

$184

Reel Paradise - Big Pine Key

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$181

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$581

Grouper Therapy

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$134

Venture Out 128

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$221

Coconut Cay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$117

Hideaway Bay

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$112

Waterside Bay

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$202

Viewing 38 of 131
rentals in Summerland Key

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