I am sure those of you with families of 5 already have researched this, but I have friends that are about to become a family of 5 any minute and they love Disney, so I was thrilled to learn that they would be able to book connecting rooms at Pop Century (and probably the other value resorts as well). Now, I did overhear on our bus to AK someone talking about having a room at Pop Century with 5 people in it (air bed was brought). I don't think they did this by listing 5 in the room, but they certainly were not hiding it, so maybe an air bed would help.
Another option for the cruise is to convince someone with 3 or less in the family to come along and put one of the kids in there. We have 17 people going in September and we are trying to talk this 'soon to be' family of 5 to come along, and one family has already offered their extra bed (they only have 1 kid) to them so they could come with only booking 1 room and then paying the extra kids rate on the other room.
DJ