When is the cheapest time to go to florida The months of late September through early December and mid-January through mid-February are the ideal times to visit. These seasons see less people, but the weather is still fantastic, thus expenses for travel, housing, and attractions are lower. Steer cleear of important holidays and times when schools are closed if you want to maybe receive cheaper pricing. If you schedule your vacation in advance and are flexible with the dates, you can save even more mony.