Florida 's most active recorded hurricane season was in 2004 , when it was hit by hurricanes Charley ( August 13 ) , Frances ( September 4 â `` 5 ) , Ivan ( September 16 ) , and Jeanne . In 2004 , Florida was hit by a record four hurricanes . Hurricanes Charley ( August 13 ) , Frances ( September 4 â `` 5 ) , Ivan ( September 16 ) , and Jeanne ( September 25 â `` 26 ) cumulatively cost the state 's economy $ 42 billion .