We went to Naples for a week and came back after 5 days because we had run out of things to do!! Fab shops but expensive designer stuff ( Versace rather than Calvin Klein) that you cant afford!!!! Other than that, there is nothing to do unless you make the 50 mile trip to the Everglades ( did that a couple of days, then could not face the journey!!)
I like St Petes and Clearwater also, but you can do those in a day trip from Kissimmee easily enough. The Sarasota Keys are two and a half hours away and really can only be done with an overnight stay which is why we picked that area for our short break.

Julie Carty