Houses Summerland Key

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Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$379

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$448

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$516

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

$765

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

$1,720

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$395

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$231

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$384

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$234

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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

$697

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

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$318

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$198

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$414

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$164

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

$557

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$286

The Helms House

Summerland Key house

  • 2 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

$466

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

$179

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

$296

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

$172

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

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

$174

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

$174

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

$172

Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Bre

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

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

$172

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

$180

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

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

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Price per night from

$574

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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Price per night from

$802

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$516

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$141

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Price per night from

$210

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Price per night from

$229

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