The Clearwater Community Sailing Center has Waves and Getaways that can be rented, along with several types of monohulls. They also offer lessons. Besides that you could go to the Dunedin Causeway and get out on one of the local sailor's cats. There is usually a pretty good assortment of Hobies, Nacras, Prindles, and Mystere's out there each weekend. Sail Honeymoon on the Dunedin Causeway also has Windrider Trimarans for rent (and kayaks).
Good Luck,