For our almost 7yo who will still nap a bit on weekends and seems to require more sleep than her younger sisters, we will likely rent in the park if she is tired and needs one.
The past two years, we rented one for her but she's just getting too tall for strollers.
If after a day or two she keeps needing one, I will call one of the off site stroller delivery companies and see if I can get one delivered to our resort.
All else equal, is prefer to have one for her. But, we already have to lug around a double for her twin sisters. And the 7yo will not fit on one side of even the biggest double strollers. Two strollers is a massive pain!