I live fairly close to Sarasota, It's a nice place. Ringling school of Art is there, That School is like the Harvard of cgi schools, Disney, EA etc recruit from there.
Lot of rich folks that way, it may not be city enough for ya though, but I don't know where you are from. It's like a 2 hr drive from Tampa and a 3hr drive from miami though, so you could take a cheap greyhound or drive or whatever if you wanted to and have some fun.
Here is a link of stuff to do there i guess.
http://www.sarasotafl.org/things-to-do/
This may be more your flavor by your description of your lifestyle.
http://www.sarasotafl.org/article/fr...der-5-dollars/
As far as the cheap listing goes, lot of people in Florida will buy a house and turn a room or all the rooms into small efficiencies and build private entrances etc.
Link to craigslist to check out usual rates over there for an apt.
http://sarasota.craigslist.org/apa/
Best of luck