Naked in Garden Hills by Harry Crews
This isn't his weirdest Florida book -- that's Karate is a Thing of the Spirit -- but in Naked in Garden Hills, Harry Crews nails the humid grotesquery of the state; Garden Hills is literally a pit where strange gathers, a town at the bottom of a quarry peopled by go-go dancers, a man made obese by weight-loss shakes, and a delusional jockey. Crews was always interested in spectacle and so his love of Florida was no mystery. But instead of just delighting in the surreal, in Naked in Garden Hills, Crews uses Florida's primary natural resource (bizarre-as-fuck-ness) to illustrate how industrialism stole the privileges of community away from small towns, displacing it with consumerism.
The Yearling by Marjorie Kinnan Rawlings
The Yearling was published about a year before To Have and Have Not and shared an editor in Maxwell Perkins. It is also overshadowed in popular memory by its film adaptation, although in this case, that's to the detriment of its source material. For some, this is a story for children about a child and his relationship with an orphaned fawn. But there aren't many books that explain Florida's complicated nature with the environment that both made the state possible and was destroyed to make way for progress. Rawlings wrote many great books about rural Florida but this is her best and most lasting, and it won the Pulitzer.