We have traveled with our kids from ages 4 months to preteen. We also love staying at Old Key West!
- You will need a stroller. I know pp's said to get a cheap one, but we always take the sit n' stand. A 4-year old will get tired and it is nice to have a place for them to rest.
- Since you are going in August it will be hot! We got a portable, battery operated fan to clip onto our stroller for the youngest.
- We always do a "travel package" for the kids for the trip. It usually has a new pair of Disney or Marvel pajamas in it, coloring items, snacks, new Disney movies, and other fun items.
- I agree with the grocery part. We have stayed 17 days before and have gotten tired of "disney" food. Having a kitchen or kitchenette helped. We could easily do breakfast in the room. We usually have a 1-bedroom so we also do full meals. Pizza places (other than Disney) will also deliver and that can be an option as well.
- Sunglasses, sunscreen, hats, comfy shoes......you probably already know that though.
- Something kind of cool.......evening EMH at HS......the Disney Jr. show turns into a dance party where kids get to dance with many different characters. It is a great interaction for them!