We're just back from staying at Pop Century and flying Southwest out of Buffalo (September 23 to Orlando and October 1 back to Buffalo).
If you are going online 24 hours in advance to get the number for each of you to board the plane (e.g. A34 etc.) I believe that once you are on the website and key in your confirmation number, all names associated with the booking appear on the screen. It's the same when you are checking your bags at the airport. It was easy and quick.
When it was 24 hours before our return flight home, one of the cast members at the concierge desk went online for us and using our confirmation number was able to secure boarding numbers for us (e.g. A34 etc), so we didn't have to worry all day.
Another great surprise was we had heard that Southwest was piloting a project at Pop Century so that you could check in your luggage at the resort for your return flight home. We didn't know if it would still be a possibility when we were there. It was. Fantastic. When we left our room in the morning there was the usual envelope hanging from the door, left by a cast member. We looked inside to find preprinted tags for each bag which indicated flight number and destination. The boarding passes were inside the envelope as well. We just took our bags to the specific location near the check in desk (outside of building near where bus picks you up) to do this. The cast member affixed the tag to each bag, checked our passports and we were then ready to board the Magical Express with just our carry-on bags to deal with. We were able to go directly to the security checkpoint at the airport.
I don't know if this now a long-term arrangement; however, the sign posted at Pop includes Southwest among the list of carriers participating in this service, so I'm thinking it may be around for a while.
Hope this information is helpful and hope too, if I've forgotten anything that someone else will provide info or correct me if I'm wrong.
Wishing you a magical trip.
All the best!
