This most recent trip (2 weeks ago) we did go back to the room most days. Some days the baby 17 months old, did nap in the room. Mostly because she feel asleep on the way home (bus or car) and we were able to transfer asleep into the pack and play. We were never able to get her to sleep herself once in the room though. So if we went back to the room and she was awake we all went swimming.
I think she slept in the room 3 or 4 days out of a 8 days total.
Some days she did nap in the stroller. I know one day we didn't go back to the room, but went from MGM to Ecpot and then later really regreated not getting the car (because the bus home for Epcot was a problem trip.)
Most days it was so cold at night we needed to dress differenlty anyway, so going back to the room was a good idea.
We just played it by ear though. No set nap time or schdule. For the most part it worked our pretty well. DD (4 years old) wanted to swim in the pool at the resort anyway (a few times she played on the playground.)
I think she slept in the room 3 or 4 days out of a 8 days total.
Some days she did nap in the stroller. I know one day we didn't go back to the room, but went from MGM to Ecpot and then later really regreated not getting the car (because the bus home for Epcot was a problem trip.)

We just played it by ear though. No set nap time or schdule. For the most part it worked our pretty well. DD (4 years old) wanted to swim in the pool at the resort anyway (a few times she played on the playground.)