Crowds at Disney World are at their worst during the summer months, from June through August. With the kids out of school, everyone wants to go to Orlando, which means long lines and hectic waits. Similar problems occur during the two weeks surrounding Christmas, the spring break period from mid-March through late April, and holiday weekends such as Columbus Day or Presidents Day. On the other hand, off-season periods such as the first two months of the year or the start of the school year in September and October are much quieter. You can get on more rides, and jaunts among the parks are much less of a hassle and hotel fares are apt to be reduced as well. The downside is that there won't be as many special events such as parades and fireworks.
It goes without saying that weekends tend to be busier at Disney World than weekdays. Some estimates show attendance on Saturdays and Sundays at twice the levels they are in the middle of the week. Regardless of the time of year, traveling during midweek days -- Tuesday, Wednesday or Thursday -- invariably means smaller crowds. Fewer specials are offered then -- the parks may close earlier and there likely won't be fireworks -- but this time lets you experience more of the resort in a much less stressful environment.
The weather in Orlando doesn't play as much of a role as it would in, say, New Jersey, but it still bears mentioning. Summer temperatures are mild yet humid, with highs in the 80s, while winter temperatures hover in the low 60s. The biggest concern with central Florida is the rain. Hurricane season runs from June through November, and though Disney World has only closed down a few times because of hurricanes, you may experience rain. The good news about the rain is that it tends to drive out the crowds, though it may affect the status of certain rides and attractions. Balance those factors out against your willingness to get wet, and bring an umbrella along if you travel there during the rainy season.