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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 / 25

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

  • 2
  • 6
  • Min stay varies

$150

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1 / 12

Blue Lagoon

  • 3
  • 6
  • 30 nights min

$201

Details

1 / 54

Waterfront - Tropical Gardens - Privacy - 3 BR

  • 3
  • 6
  • 14 nights min

$157

Details

1 / 14

Egret's Landing

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 15

House of the Sun

  • 3
  • 6
  • 30 nights min

$181

Details

1 / 15

Owl's Nest

  • 3
  • 6
  • 30 nights min

$120

Details

1 / 11

Barbados Isle

  • 3
  • 6
  • 30 nights min

$113

Details

1 / 14

Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 19

Charming 3bedroom/2bath home in the Florida Keys

  • 3
  • 6
  • 30 nights min

$93

Details

1 / 19

Bahia Azul

  • 4
  • 8
  • 30 nights min

$231

Details

1 / 13

Casa Rosa

  • 2
  • 4
  • 30 nights min

$108

Details

1 / 20

Paradise n Summerland Key Cove

  • 3
  • 10
  • 30 nights min

$119

Details

1 / 14

Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 23

Mobile Home in Venture Out Sleeps 5 Mile Marker 23

  • 2
  • 6
  • 7 nights min

$89

Details

1 / 35

Oceanfront House

  • 3
  • 8
  • 30 nights min

$334

Details

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1 / 15

Summerland Place

  • 3
  • 6
  • 30 nights min

$118

Details

1 / 15

Pirate's Cove

  • 2
  • 4
  • 30 nights min

$71

Details

1 / 11

St. Croix

  • 2
  • 4
  • 30 nights min

$89

Details

1 / 14

Cudjoe Cottage

  • 2
  • 4
  • 30 nights min

$114

Details

1 / 15

Breezy Palms

  • 3
  • 6
  • 30 nights min

$140

Details

1 / 19

Lafitte Landing

  • 2
  • 4
  • 30 nights min

$95

Details

1 / 11

Boaters Paradise in Ramrod Key

  • 3
  • 8
  • 30 nights min

$134

Details

1 / 16

Tropical Bay

  • 3
  • 5
  • 30 nights min

$83

Details

1 / 19

Atlantic Breeze

  • 3
  • 6
  • 30 nights min

$134

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 / 8

Quiet Waters

  • 3
  • 6
  • 30 nights min

$90

Details

1 / 27

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

  • 5
  • 10
  • 30 nights min

$667

Details

1 / 30

Villa Marquesa in Ramrod Key Florida keys

  • 4
  • 12
  • 30 nights min

$140

Details

1 / 12

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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1 / 20

Fabulous Florida Keys!

  • 2
  • 6
  • 7 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

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