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Pets allowed
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111 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

$558

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$319

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$380

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$198

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$518

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

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$415

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$289

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

$1,725

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

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$701

Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Do

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$173

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Do

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$159

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$287

Into the Mystic

Summerland Key house

6 bedrooms
6 bathrooms

sleeps 12

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Price per night from

$467

Oceanview Cottage: Embrace Island Living with Sandy Toes and Breathtaking Open W

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$173

Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple F

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$180

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$288

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapi

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$297

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock &

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$181

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$397

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$231

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$175

The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room fo

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$175

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$144

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$114

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$204

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$258

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$268

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$141

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$236

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

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Price per night from

$148

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$144

Margarita Villa

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$189

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$151

Our Island Thing

Big Pine Key house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$279

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$231

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$121

Viewing 38 of 111
rentals in Summerland Key

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Summerland Key Rentals

Per night

111 Houses

Viewing 38 of 111rentals in Summerland Key

Also consider

Viewing 38 of 111
rentals in Summerland Key