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

1 / 12

Chickies Conch Cottage

  • 2
  • 4
  • 30 nights min

$93

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1 / 8

Blue Marlin

  • 3
  • 6
  • 30 nights min

$125

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1 / 19

Sunset Bay (weekly rental)

  • 2
  • 4
  • 7 nights min

$255

Details

1 / 12

Blue Lagoon

  • 3
  • 6
  • 30 nights min

$201

Details

1 / 15

House of the Sun

  • 3
  • 6
  • 30 nights min

$181

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1 / 22

Caribbean Dream

  • 4
  • 8
  • 30 nights min

$201

Details

1 / 10

Blue Heron

  • 2
  • 4
  • 30 nights min

$87

Details

1 / 10

Ramrod Retreat

  • 3
  • 6
  • 30 nights min

$98

Details

1 / 18

Big Torch Retreat

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 15

Barry Beach (weekly Rental)

  • 4
  • 8
  • 7 nights min

$429

Details

1 / 20

Key Z Cottage Romantic Getaway

  • 2
  • 6
  • 3 nights min

$238

Details

1 / 14

Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 20

Paradise n Summerland Key Cove

  • 3
  • 10
  • 30 nights min

$119

Details

1 / 18

Pirates Pointe

  • 3
  • 6
  • 30 nights min

$120

Details

1 / 13

Casa Rosa

  • 2
  • 4
  • 30 nights min

$107

Details

1 / 35

Oceanfront House

  • 3
  • 8
  • 30 nights min

$334

Details

1 / 11

Barbados Isle

  • 3
  • 6
  • 30 nights min

$113

Details

1 / 14

Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 13

Gulf Shores

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 15

Breezy Palms

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 11

Boaters Paradise in Ramrod Key

  • 3
  • 8
  • 30 nights min

$134

Details

1 / 13

Dolphin Beach

  • 3
  • 6
  • 30 nights min

$233

Details

1 / 16

Charming Elevated Waterfront Home

  • 1
  • 4
  • 30 nights min

$143

Details

1 / 38

Beautiful Canal Home - Minutes From Open Water

  • 3
  • 8
  • 30 nights min

$150

Details

1 / 23

Palm Villa

  • 3
  • 6
  • 30 nights min

$187

Details

1 / 18

Cruikshank

  • 3
  • 6
  • 30 nights min

$169

Details

1 / 12

Coral House

  • 3
  • 6
  • 30 nights min

$119

Details

1 / 30

Villa Marquesa in Ramrod Key Florida keys

  • 4
  • 12
  • 30 nights min

$140

Details

1 / 27

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

  • 5
  • 10
  • 30 nights min

$667

Details

1 / 16

Keys Breeze

  • 2
  • 4
  • 30 nights min

$93

Details

1 / 10

Mango House

  • 2
  • 4
  • 30 nights min

$68

Details

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1 / 15

Casa Serenity

  • 3
  • 6
  • 30 nights min

$120

Details

1 / 16

Conch Out

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 19

Big Pine Getaway

  • 3
  • 6
  • Min stay varies

$154

Details

1 / 7

Blue water paradise

  • 3
  • 6
  • 30 nights min

$150

Details

1 / 20

Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$233

Details

1 / 13

Oceanfront Home Rental in Ramrod Key, Florida

  • 3
  • 6
  • Min stay varies

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