Summerland Key Rentals

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Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$447

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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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

$764

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

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

$698

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

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$383

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

$230

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

Match: Balcony or terrace

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Price per night from

$174

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

Match: Balcony or terrace

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Price per night from

$174

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

Match: Balcony or terrace

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Price per night from

$179

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

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Price per night from

$233

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

Match: Balcony or terrace

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Price per night from

$144

Great rentals within 20 miles that match your search

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

Match: Balcony or terrace

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Price per night from

$516

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,946

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$773

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Price per night from

$210

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Price per night from

$228

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$207

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$177

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$140

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$258

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$183

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$173

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$170

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$224

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$218

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$252

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$157

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

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Price per night from

$344

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

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Price per night from

$800

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$5,720

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Balcony or terrace

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Price per night from

$773

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$258

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

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$516

Match: Balcony or terrace

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Price per night from

$263

Match: Balcony or terrace

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Price per night from

$859

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