Was Tom Petty correct to think he was cursed by the critics for sounding so "normal"? I'd rather listen to Tampa Red or Cannonball Adderly. You can list many people who spent winters in Florida, or died there, but they don't quite count. Ernest Hemingway had a close enough tie to Key West and I favor his short stories over his novels. Zora Neale Hurston is still worth reading. Carl Hiaasen is true Florida but I've never finished one of his books. Juanes lives in Miami and he has five or so very good pop songs, maybe more. Celia Cruz ended up there too and I suspect many other Latino musicians did as well. In sum that list probably would be very impressive. Purvis Young is a good "Outsider" artist.
Many excellent movies are set in Florida. Where do I start?
Body Heat. The underrated Wild Things. Key Largo. Contact. Deuce Bigelow. Ace Ventura (a favorite). Various space launch movies. The superb Ulee's Gold. Parts of Midnight Cowboy. Didn't Elliott Gould and Robert DeNiro end up there every now and then? I feel there are additional noir movies and parts of gangster movies. I Dream of Jeannie was set there.
Miami has long been one of my favorite American cities and I like Tampa for its dumpiness. Naples is boring.