Part of my family is going to be in Disney for a week and the other part five days. We are considering two rooms at Pop. In this case could we still have a chance at connecting rooms even though one party will be staying less time? Thank you!
Sure but you will not be able to book them on the same reservation. You will only be able to "Request" Connecting rooms and have each reservation updated to indicate that your are traveling with the other reservation number. When the first party leaves you / they just closes the connecting doors.
Much easier of you are arriving on the same day, which it sounds like you are. If you are not, then that is a lot more difficult to manage and I wouldn't count on connecting. They will do their best, but it's never guaranteed, especially since it's two different travelling parties. If it comes down to shortage of availability, they will more likely give the connecting rooms to parties of 2 adults with children.