Houses Summerland Key

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33 houses

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Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Bicycles available

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Price per night from

$378

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Bicycles available

All filters match

Price per night from

$447

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Bicycles available

All filters match

Price per night from

$516

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

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$161

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$197

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$317

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$287

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$413

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$163

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

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$764

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

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$1,718

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$230

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$233

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$383

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$285

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$286

Into the Mystic

Summerland Key house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$465

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

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$556

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$395

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$174

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$172

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$172

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$179

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$180

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$172

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$174

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$144

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

1 of 2 match: Bicycles available, Rental types

1 of 2 filters match

Price per night from

$296

Great rentals within 20 miles that match your search

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Bicycles available

All filters match

Price per night from

$172

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Bicycles available

All filters match

Price per night from

$207

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Bicycles available

All filters match

Price per night from

$252

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types Bicycles available

All filters match

Price per night from

$516

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Rental types Bicycles available

All filters match

Price per night from

$5,720

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