Summerland Key Rentals

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9 Houses

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Tennis in town

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Price per night from

$516

Great rentals within 20 miles that match your search

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$760

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$746

Waterfront Haven House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$459

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Tennis in town

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Price per night from

$5,741

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Tennis in town

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Price per night from

$367

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!!!

Match: Tennis in town

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Price per night from

$344

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Tennis in town

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Price per night from

$457

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Tennis in town

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Price per night from

$801

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