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Boats running down the wide green water of Snake Creek in Islamorada

The Florida Keys · 206 licensed rentals

Islamorada vacation rentals

Photo: Sharon Hahn Darlin · CC BY 2.0

Islamorada is a village spread across several keys: Plantation Key, Windley Key, and Upper and Lower Matecumbe. It calls itself the sport fishing capital of the world, and the docks back that up, with offshore charters running out to the Gulf Stream and flats guides poling the shallows for bonefish and tarpon.

Rentals here lean toward waterfront homes with docks and bayside spots that face the sunset over Florida Bay. Off the water the pace is easy: Anne's Beach on Lower Matecumbe, the History of Diving Museum, and the Hurricane Monument on Upper Matecumbe, which honors the people lost in the 1935 Labor Day hurricane that also ended the railroad through the Keys.

Things to do near your rental

  • Anne's Beach on Lower Matecumbe Key
  • Windley Key Fossil Reef Geological State Park
  • Boat trips to Indian Key and Lignumvitae Key historic state parks
  • History of Diving Museum

Licensed by the state of Florida

206 Islamorada vacation rentals

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