PDub:

About 3 years ago I spent > 4 months in the Tampa/Clearwater area...some parts of Tampa are not great, some terrific... Clearwater is a 'home run'...is about a 30-45 minute ride from Tampa, has a terrific beach with decent restaurants. At that time of year you won't have an issue in getting a reservation at a nice hotel. The weather might be cool at night (65) but should be plenty warm for swimming in the day. The Tampa airport is one of the best in the country in ease of access and Tampa Bay racetrack WILL be open that time of year...is definitely worth a visit or 2 or 3!