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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 / 13

Paradise on Cudjoe Bay

  • 2
  • 6
  • 3 nights min

$258

Details

1 / 54

Waterfront - Tropical Gardens - Privacy - 3 BR

  • 3
  • 6
  • 14 nights min

$156

Details

1 / 23

Mobile Home in Venture Out Sleeps 5 Mile Marker 23

  • 2
  • 6
  • 7 nights min

$89

Details

1 / 19

Sunset Bay (weekly rental)

  • 2
  • 4
  • 7 nights min

$254

Details

1 / 12

Coral House

  • 3
  • 6
  • 30 nights min

$118

Details

1 / 10

Ramrod Retreat

  • 3
  • 6
  • 30 nights min

$97

Details

1 / 14

Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$139

Details

1 / 14

Cove Isles

  • 2
  • 4
  • 30 nights min

$110

Details

1 / 19

Charming 3bedroom/2bath home in the Florida Keys

  • 3
  • 6
  • 30 nights min

$93

Details

1 / 14

Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 22

Caribbean Dream

  • 4
  • 8
  • 30 nights min

$199

Details

1 / 11

Barbados Isle

  • 3
  • 6
  • 30 nights min

$112

Details

1 / 15

Island Living

  • 3
  • 8
  • 30 nights min

$149

Details

1 / 15

House of the Sun

  • 3
  • 6
  • 30 nights min

$179

Details

1 / 15

Breezy Palms

  • 3
  • 6
  • 30 nights min

$139

Details

1 / 16

5 O'Clock Somewhere

  • 2
  • 4
  • 30 nights min

$87

Details

1 / 25

Oksana's Tropical Beach Oasis

  • 5
  • 14
  • 7 nights min

$475

Details

1 / 11

Boaters Paradise in Ramrod Key

  • 3
  • 8
  • 30 nights min

$132

Details

1 / 14

Egret's Landing

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 11

Mermaid's Rest

  • 3
  • 6
  • 30 nights min

$127

Details

1 / 18

Family Retreat Oceanfront Home with Pool

  • 6
  • 18
  • Min stay varies

$528

Details

1 / 14

Cudjoe Cottage

  • 2
  • 4
  • 30 nights min

$113

Details

1 / 15

Summerland Place

  • 3
  • 6
  • 30 nights min

$117

Details

1 / 19

Bahia Azul

  • 4
  • 8
  • 30 nights min

$229

Details

1 / 13

Dolphin Beach

  • 3
  • 6
  • 30 nights min

$232

Details

1 / 18

Big Torch Retreat

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 12

Paradise Bay

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 35

Oceanfront House

  • 3
  • 8
  • 30 nights min

$331

Details

1 / 13

Gulf Shores

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 12

Ocean Breeze

  • 3
  • 6
  • 30 nights min

$162

Details

1 / 15

Kopi Key Place

  • 3
  • 6
  • 30 nights min

$113

Details

1 / 15

Casa Serenity

  • 3
  • 6
  • 30 nights min

$120

Details

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1 / 20

Fabulous Florida Keys!

  • 2
  • 6
  • 7 nights min

$120

Details

1 / 7

Blue water paradise

  • 3
  • 6
  • 30 nights min

$149

Details

1 / 13

Oceanfront Home Rental in Ramrod Key, Florida

  • 3
  • 6
  • Min stay varies

Inquire for Rates

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1 / 20

Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$232

Details

1 / 23

Water view Key West vacation from owner

  • 4
  • 8
  • 7 nights min

$511

Details

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