8. Hurricane Charley ($21.21B). August 13, 2004 (Cat 4). 35 deaths, damages of $21.21B per one source, $16.3B per another. 150 mph wins at peak. Destructively crossed over Cuba August 13 as Cat 3 then hit Captiva Island, Florida August 13, 2004, then made continental landfall near Port Charlotte about 5 PM, and continued north, passing through Orlando. The entire pass through Florida took only 7 hours.
7. Hurricane Rita ($23.7B). September 24, 2005 (Cat 3). Winds reached 180 mph. Death toll was between 97 and 125 (officially 120). Damages were listed as $23.7B in one source and $12B in another source. Previously a Category 5 storm, it made landfall as Cat 3 between Sabine Pass, TX and Holly Beach, LA September 24, 2005, 7:40 UT. Coming about a month after Hurricane Katrina, it exacerbated problems already existing in Louisiana particularly. Though Rita did not make landfall in Florida, the winds and rain caused great havoc and damage.
6. Hurricane Wilma ($29.4B). October 24, 2005 (Cat 3). 87 deaths. $29.4 billion in damages (2005). 185 mph winds / Category 5 at peak. Noteworthy as the "most intense tropical cyclone ever recorded in the Atlantic basin" and, until Hurricane Patricia in 2015, the most intense in the western hemisphere. First U.S. landfall (following a highly destructive swipe across Yucatan) was October 24, 2005, 6:30 AM, in Cape Romano, FL as a Cat 3. Crossing Florida to the Atlantic, it sped northward fast, reaching Nova Scotia by October 26 as an extratropical cyclone.
5. Hurricane Ivan ($27.1B). September 16, 2004 (Cat 3). 124 deaths. 165 mph winds. It struck Grenada catastrophically and tore through the Caribbean. In the U.S. it especially hit Florida and Alabama. First U.S. landfall was in Florida September 16, 2004. 6:50 UT just west of Gulf Shores, AL.
4. Hurricane Ike ($37.5B). September 13, 2008. 195 deaths (74 in Haiti) + 16 missing. 145 mph winds. It was the most destructive hurricane in Cuban history. Landfall in Cuba (near Puerto de Sama) September 8. Landfall at Galveston Island, TX 2:10 AM September 13, 2008.