the main strip (beach blvd and shore blvd) has decent restaurants/bars. would recommend staying as close to waterfront as possible, shaky areas north. the southwest side has pasadena golf and yacht club, look for rentals there, not sure what maybe available. jan-feb are beginning of season, so there is more traffic, but it still flows okay.
i would look at gulfport, st petersburg, st petersburg beach city websites for activities.
I don't mind coming to w**k,
but that eight hour wait to go home is just bulls**t!