When is the cheapest time to go to florida The best times to travel are from mid-January to mid-February and from late September to early December. Although there are less tourists during these times, the weather is still great, and as a result, airfare, lodging, and attraction costs are reduced. Finding better deals might also be aided by avoiding popular holidays and times when schools are closed. Further cutting expenses can be achieved by making reservations far in advance and being flexible with your travel dates.