Which airline?
I usually book as soon as fares are released. We generally fly non-stop CAK to MCO. We fly AirTran. If the price drops, you can call for a credit to your account to be used for purchase at a later date. The credit is only good 1 year from original booking date. We travel to FL twice a year and don't have trouble spending the credit. The credit can also be used to pay baggage fees or seat upgrades.
Our Dec. 2011 trip was booked at $124. each way. Till it came time for the trip, I had the tickets down to $89. each way.
If you don't already use Yapta.com you may want to go to their website and sign up. They track your flights for you and send an email when the price drops.
If you can get a credit should the price drop, I'd go ahead and book.