We bought a Chicco umbrella stroller for $60 when we took the 18 MO GrandPrincess in May so we were using it for free after the 6th day. A little different issue with a 5 YO because we had to use one as young as she is. We found that we could park the stroller in one of the stroller areas at an attraction close to the front of the park when we were going back to the resort for naptime (if only 1 of us was going back for the nap, it was a hassle to deal with the stroller and a tired GrandPrincess) and it was always there a few hours later when the nap was over and we'd come back to that park. If you decide on taking an umbrella stroller, you could park it somewhere until later in the day when your 5 YO gets tired or even just to use for the back to resort trek.