As kids head back to school and crowds start to drop, so do some travel prices. September is one of the cheapest months to fly to Florida. Save even more by booking weekday flights in the afternoon. Also, keep an eye out for shoulder-season deals at luxury hotels. For example, the acclaimed Fontainebleau in Miami Beach has a Fall for Bleu promotion, which offers savings of up to 25% off plus a $100 resort credit when you stay four nights or longer.