We are a family of three, and our daughter is two-and-a-half, which is part of the reason we are planning a trip now! Before kids, I said I wouldn't take a two-year-old to Disney, but she is such an easy kid and loves the princesses, so we're taking advantage of her "free" ticket and going now!
Our costs:
Five nights at POR in a royal guest room (yay!) with three-day base tickets: $1,675
Flights direct from Michigan to Tampa-St. Petersburg with rental car: $850
Dining: $700
The room was booked with the spring "up to 30% off" offer. We like having a rental car and flights to the smaller St. Pete airport from where we live are cheap, so that is a good value for us. Our food would be much less, but there is an Orlando restaurant we love (Roy's) and we splurge when we go there. I also plan to spent about $100 on groceries for the room (I'd be lying if I said I wasn't excited to shop at Publix) and also drop some dough on souvenirs, this being DD's first Disney trip. I think we did pretty well trying to keep this trip fairly cheap - we could have gone cheaper with a value, but we really love POR and the other moderates.
Spending nearly $10K for a two-week trip doesn't surprise me. I always like to play on the Disney website, putting together elaborate trips and trying to get them up to $20K, which is certainly possible!