We go to Orlando quite a bit since we only live a couple hours away in St Petersburg. People are always asking me when is the best time to visit and get a hotel room. I really think the best time is when your vacation allows it and that's probably more of a work-related issue. I would stay away from getting a hotel whenever it's too cold out to take advantage of the swimming pools. Just because they have the pools heated does not mean that you're going to want to go in them. I would stay away from January, February, and March. That is the peak time where everything is more expensive anyway, as people are coming down from up north. Even on a sunny day when it's sixty three degrees, with a twenty mile an hour wind, swimming in the pool all of a sudden became such no fun. You need to be able to get in easily and get out easily without your body going into hypothermia or shock!