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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 / 19

Sunset Bay (weekly rental)

  • 2
  • 4
  • 7 nights min

$255

Details

1 / 15

House of the Sun

  • 3
  • 6
  • 30 nights min

$181

Details

1 / 11

Mermaid's Rest

  • 3
  • 6
  • 30 nights min

$128

Details

1 / 16

5 O'Clock Somewhere

  • 2
  • 4
  • 30 nights min

$88

Details

1 / 12

Blue Lagoon

  • 3
  • 6
  • 30 nights min

$201

Details

1 / 19

Charming 3bedroom/2bath home in the Florida Keys

  • 3
  • 6
  • 30 nights min

$93

Details

1 / 23

Mobile Home in Venture Out Sleeps 5 Mile Marker 23

  • 2
  • 6
  • 7 nights min

$89

Details

1 / 22

Caribbean Dream

  • 4
  • 8
  • 30 nights min

$201

Details

1 / 20

Paradise n Summerland Key Cove

  • 3
  • 10
  • 30 nights min

$119

Details

1 / 13

Casa Rosa

  • 2
  • 4
  • 30 nights min

$108

Details

1 / 11

Barbados Isle

  • 3
  • 6
  • 30 nights min

$113

Details

1 / 15

Owl's Nest

  • 3
  • 6
  • 30 nights min

$120

Details

1 / 14

Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 14

Cove Isles

  • 2
  • 4
  • 30 nights min

$110

Details

1 / 15

Breezy Palms

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 11

St. Croix

  • 2
  • 4
  • 30 nights min

$89

Details

1 / 12

Ocean Breeze

  • 3
  • 6
  • 30 nights min

$164

Details

1 / 12

Caribbean House

  • 2
  • 4
  • 30 nights min

$83

Details

1 / 12

Paradise Bay

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 19

Bahia Azul

  • 4
  • 8
  • 30 nights min

$231

Details

1 / 13

Dolphin Beach

  • 3
  • 6
  • 30 nights min

$233

Details

1 / 14

Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 19

Lafitte Landing

  • 2
  • 4
  • 30 nights min

$95

Details

1 / 15

Summerland Place

  • 3
  • 6
  • 30 nights min

$118

Details

1 / 14

Cudjoe Cottage

  • 2
  • 4
  • 30 nights min

$114

Details

1 / 19

Atlantic Breeze

  • 3
  • 6
  • 30 nights min

$134

Details

1 / 15

Kopi Key Place

  • 3
  • 6
  • 30 nights min

$114

Details

1 / 28

Tropical Canal Home

  • 3
  • 6
  • 30 nights min

$167

Details

1 / 15

Island Living

  • 3
  • 8
  • 30 nights min

$150

Details

1 / 12

Coral House

  • 3
  • 6
  • 30 nights min

$119

Details

1 / 27

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

  • 5
  • 10
  • 30 nights min

$667

Details

1 / 20

Fabulous Florida Keys!

  • 2
  • 6
  • 7 nights min

$120

Details

1 / 15

Casa Serenity

  • 3
  • 6
  • 30 nights min

$120

Details

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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

Inquire for Rates

Details

1 / 4

Oceanfront vacation property with a variety of amenities. Rents weekly

  • 1
  • 4
  • 7 nights min

$140

Details

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