There are a lot of variables to fully answering this question. For us, if we have the dining plan, we don't bring much extra money. I would think $300 for 4 nights would be plenty. It would be more than enough for my family. To us, the dining plan offers enough food that we don't spend very much on extra things. I'm talking $50 or less for extra food/snacks for the while trip. Then we spend $50 or less on each of our children and very rarely get much for ourselves. They usually get something to wear, something to play with, and something special to eat. That being said, my sis is a CM and we go often so big souvenirs are a necessity every time. We are going in Oct for 3 nights and I have set aside $200 on top of everything for souvenirs, extra snacks, etc. You can really get by with taking as little or as much as much as you want. It is totally a personal preference.