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When is the cheapest time to go to florida traveling to Florida in the late summer and early fall, specifically from August to mid-October, is usually the most affordable. Although it's hurricane season, the weather is still warm during this time, which may discourage some people and result in cheaper airfares and hotel rates. Costs can also be decreased by traveling during the week rather than the weekend and by skipping public holidays. By scheduling your vacation during these off-peak periods, you may visit Florida's beaches and attractions without the typical crowds and at a price that is more affordable.