Howdy, Brandee!
Visiting Disney between September and December is a great time of year. The temperatures are mild and the holiday season is in full effect! Halloween at Walt Disney World is from August until the first of November and then the Christmas Season begins immediately after Halloween. Anytime around a holiday, the crowds will be larger, such Labor Day, Halloween, Thanksgiving Day, and Christmas Day/New Year's Eve. If you are interested in visiting when crowds are less and want to experience Disney in all of it's Christmas splendor, I would suggest going the week before Thanksgiving or Christmas. For the Halloween/fall decorations and the Food and Wine Festival, visiting at the end of September or first of October is a great time.
For a family of 5 with school aged children, Disney's Art of Animation offers themed suites, which will give your family plenty space and beds to sleep. Suites are available in all of the buildings except the Little Mermaid themed rooms. The theming at this resort is spectacular. Larger than life Disney characters greet you throughout this resort, and the pools are really fun too! Disney Contemporary Resort is on the Monorail line and has character dining on site at Chef Mickey's.
Love Chef Mickey's! The rooms at this resort aren't as colorful and appealing to younger guests, but your family will definitely enjoy watching the Monorail from inside the Resort. Suites are also available. My family loves staying so close to the Magic Kingdom when we decide to stay at Disney's Contemporary Resort.
Brandee, you know your little ones best and what they would enjoy most. Just know that whatever decision you make, you'll be at Disney! Fun will be had by all regardless!
Please visit with us again if you have more questions!
Korliss