Summerland Key Vacation Home Rentals, Treehouses & More


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Travelers going to Summerland Key are booking December dates now. Secure your vacation rental today and have the perfect trip.

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Dolphin Beach

  • 3
  • 6
  • 30 nights min

$234

Details

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Oceanfront House

  • 3
  • 8
  • 30 nights min

$334

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Summerland Place

  • 3
  • 6
  • 30 nights min

$117

Details

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Caribbean Dream

  • 4
  • 8
  • 30 nights min

$200

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Big Torch Retreat

  • 3
  • 6
  • 30 nights min

$100

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Gulf Shores

  • 3
  • 6
  • 30 nights min

$100

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Blue Lagoon

  • 3
  • 6
  • 30 nights min

$200

Details

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Cruikshank

  • 3
  • 6
  • 30 nights min

$168

Details

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Villa Cayo

  • 3
  • 6
  • 30 nights min

$267

Details

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Cove Isles

  • 2
  • 4
  • 30 nights min

$110

Details

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Caribbean House

  • 2
  • 4
  • 30 nights min

$84

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Casa Turquesa

  • 3
  • 6
  • 30 nights min

$207

Details

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Paradise n Summerland Key Cove

  • 3
  • 10
  • 30 nights min

$119

Details

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Ocean Breeze

  • 3
  • 6
  • 30 nights min

$164

Details

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Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$200

Details

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MELODY KEY - PRIVATE ISLAND

  • 3
  • 8
  • 6 nights min

$1250

Details

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Family Friendly House In Paradise

  • 5
  • 8
  • 30 nights min

$184

Details

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

  • 5
  • 10
  • 30 nights min

$667

Details

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Island Living

  • 3
  • 8
  • 30 nights min

$150

Details

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Water view Key West vacation from owner

  • 4
  • 8
  • 7 nights min

$500

Details

3
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Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$233

Details

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Great rentals within 30 miles that match your search

1 / 25

Waterfront 2/2 with 35' Dock in the Lower Keys

  • 2
  • 6
  • Min stay varies

$140

Details

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Cudjoe Ocean Shores

  • 3
  • 6
  • 30 nights min

$97

Details

1 / 20

Fabulous Florida Keys!

  • 2
  • 6
  • 7 nights min

$120

Details

9
1 / 23

Mobile Home in Venture Out Sleeps 5 Mile Marker 23

  • 2
  • 6
  • 7 nights min

$129

Details

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Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board

  • 2
  • 6
  • Min stay varies

$135

Details

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Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

  • 2
  • 6
  • 3 nights min

$149

Details

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Charming 3bedroom/2bath home in the Florida Keys

  • 3
  • 6
  • 30 nights min

$94

Details

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Quiet Waters

  • 3
  • 6
  • 30 nights min

$90

Details

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Pirate's Cove

  • 2
  • 4
  • 30 nights min

$70

Details

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Tropical Canal Home

  • 3
  • 6
  • 30 nights min

$167

Details

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1 / 23

Tropical Blue Adventure Waterfront at Venture Out

  • 2
  • 6
  • 2 nights min

$157

Details

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Priv Home & Launch $3295 1wk, $ 3750 2 wks, $4903 3 wks Spectacular ocean views

  • 2
  • 6
  • 7 nights min

$428

Details

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Tropical Bay

  • 3
  • 5
  • 30 nights min

$84

Details

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Bahia Azul

  • 4
  • 8
  • 30 nights min

$230

Details

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Paradise Bay

  • 3
  • 6
  • 30 nights min

$100

Details

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Owl's Nest

  • 3
  • 6
  • 30 nights min

$120

Details

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