I am on my way to Key West next week! I go several times a year. Although winter is more appealing, the prices are not. After May 1st and probably up to Oct. 1st are your best deals.I have some friends in the tourism business there that may have some suggestions. You would definatly need to plan NOW for next summer. You may find that you might have to back the event up to 2014 if you need alot of accomodations.
I would be glad to help in any way. Count me in!