B.B. Hemingway

Went to Hollywood Florida a few years ago in Feb and drove down to Key Largo. I was a bit underwhelmed with Key Largo but if you fly directly into KeyWest it probably would be worth it. I really liked Hollywood Beach. We got an Air BnB near there boardwalk and we had a blast. Amazing food. Amazing beaches. 

My brother lived in Key West for a few years while he was in the Navy and I went to visit him several times.  Once you get away from Duval Street and the touristy areas you'd be amazed at how crappy it actually is.  Some people like it but it wasn't for me.  Good seafood though.  Ever been to Charleston or Savannah?  They're close enough you could knock both out in a trip if you have a car.  Hilton Head is great too if you like golf.