If you're willing to pay for deluxe resorts, I think there are quite a few rooms that sleep 5 at those resorts. The only moderate with room for 5 of which I am aware is Port Orleans Riverside with trundle bed. We've fit 6 in a FW cabin and loved the living room and full kitchen. You may not want to pay for the luxury, but you can fit 5 in a 2 bedroom villa at any of the DVC properties or easily fit into a 1 bedroom since you've got someone under 3 that you don't have to count. One bedroom villas are only approved for 4 people plus one under 3 in pack-n-play, but if you got a room with 2 doubles/queens? in the bedroom then you wouldn't need the pack and play as there is a pull out couch bed in the living room and there would be enough beds. (I wish you were permitted more than 4 in a one bedroom because I count beds for 6 if you're two people per double in a room with two beds in the bedroom... I guess they can't guarantee you two doubles vs. king in the bedroom. But I neither break nor make the rules. Though if your youngest is like ours, you could use a king bed for little one between you and spouse...) Just some ideas. I've never seen the 5 person deluxe rooms nor the new family suites personally.
