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Cheeca Lodge's history began in 1946, when Mrs. Clara Mae Downey, owner of the Olney Inn outside Washington, D.C., built the Islamorada Olney Inn on the present site. The next owners were the heirs of the A & P grocery chain, Carl and Cynthia "Che-Che" Twitchell, who totally rebuilt and renamed the resort "Cheeca" by merging their names. Cheeca was purchased by Coca-Cola bottler Carl Navarre in the 1970's. The Navarre family still maintains a home on the property. Today, Cheeca Lodge is owned by Cheeca Holdings, LLC and it is managed by Rock Resorts the luxury arm of Vail Resorts of Vail, Colorado.
The Pioneer Cemetery
The cemetery at Cheeca Lodge & Club memorializes the determination and vision of more than 50 pioneer Anglo-Bahamian Conchs who labored to settle and organize the first community on Matecumbe Key.
Descendants of three Islamorada pioneer families, the Russells who homesteaded in 1854, the Pinders in 1873, and the Parkers in 1898, are buried on this land. Deeded to Richard Pinder on January 20, 1883, by President Chester A. Arthur, the cemetery land is now the property of the Matecumbe United Methodist Church.
North and adjacent to the cemetery lay the first church on the key. Built in 1884 and transported to this site by raft sometime around 1890, the church was later replaced by a coral-rock building.
A raging hurricane struck Islamorada on Labor Day in 1935, killing 50 members of the Russell family alone. The storm also destroyed the church, the schoolhouse and the "Millionaires' Row" of beach front homes adjacent to this property. The survivors' descendants rebuilt their homes, and a new church and a school west of this site and east of Henry Flagler's Overseas Railway, now U.S. Highway 1.
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