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I know it's a hard choice to decide when working with a budget! We have gone to Disney World about 12 times and have only stayed off property once,(when we chaperoned a high school show choir group), and we hated it. We don't spend alot of time at our resort so room size isn't a priorty for us. Of course traveling with a baby or small children is a whole other story! When our son was small, it was such an advantage to just hop a bus back to the resort for a nap, I haven't really figured out if our son or dad needed the nap(ha) We have found so many other ways to stretch the budget without having to give up staying on property.
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