Hi Stephanie!
Thanks for the question! When to go is a really popular question, and really it comes down to personal preference. If you can prioritize budget, weather and crowds it will help you narrow down your options.
Personally, I consider crowds, budget then weather. So my favorite time to visit is January, simply because typically you’ll have the lowest crowds of the year. Although the weather can be relatively cool in January, it’s a pretty good bet that it will be warmer than it would be at home (and no snow). This is the value season at Walt Disney World, so you’ll have a better chance of getting a great promotional deal.
That being said, we have traveled in November several times. The weather tends to be warmer during the day, but the crowds are slightly heavier. I would suggest you avoid the U.S. Thanksgiving holiday week as the crowd levels elevate significantly.
For our family of five, we either stay in a two-bedroom deluxe villa, or get connecting rooms at a moderate resort; Coronado Springs Resort is our favorite.
Hope this helps!