Main Street. This is a cute little town where you can walk to everything within a few blocks. They have shops, restaurants and bars.
This is a great town by the water where you can walk to many shops, bars and restaurants. It is a bit of a walk but a great place to visit.
Sand Key Beach is a great beach. It is not overly crowded and parking is a reasonable fee. It is not far from Clearwater Beach, however, Clearwater Beach is extremely crowded in the summer and parking is very expensive.
St. Pete Beach is a bit further of a ride (maybe about 30-40 minutes from Clearwater) but their beaches are beautiful.