Boston to Orlando runs on the school calendar. Massachusetts February vacation, the week of April vacation around Patriots' Day, and the Christmas weeks send thousands of families south, and fares follow them. Outside those weeks, the route is much cheaper and calmer.
If you have any freedom with dates, that is the single biggest lever. Shifting a trip by one week to avoid a vacation period can save hundreds of dollars for a family of four, and Orlando is no less fun in the weeks around the school breaks.
