When is the cheapest time to go to florida The best times to go are from late September to early December and from mid-January to mid-February. Although there are less tourists during these seasons, the weather is still great, thus airfare, lodging, and attraction costs are reduced. If you want to perhaps get better rates, avoid major holidays and times when schools are closed. You can save even more money by planning ahead of time and being flexible with the dates of your vacation.