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I have been to Vegas every month of the year. The best time for me (weatherwise) would be September/ late May-early June. The cheapest time- July, August, December between the ending of the rodeo and a few days before NYE. The most expensive time- no contest- NYE.
Best Times to Visit Orlando-Walt Disney World. The best time to visit Orlando is January to April. That's the time of year you'll find the most pleasant weather (mid-70s most days) and agreeable prices on travel and lodging.