Hi, Nichole!
First of all, I love that you are making the effort to ensure you son's comfort; a happy child makes for a much better trip to Walt Disney World!
There is no reason for you to feel nervous or concerned about what people might think about your son in a stroller. Lots of children older than that are in strollers, both brought from home and
rented at the Parks. And they are on harnesses, and they are in carriers, and they are in backpacks ... the list goes on.
But if you have mixed feelings, give one of the Parks an "audition" without the stroller. see how he does (all the while observing the number of older children riding in style!), and how long he lasts without it. You can always leave the Park and retrieve the stroller from the Resort of rental car, wherever you are keeping it.
Above all, it doesn't matter what anyone else thinks. This is
your long-awaited family trip, and you should do what works best for
your crew. The objective is to arrive -- and leave! -- feeling the Magic.
Happy strolling!
See you later, celebrator!
-Deborah B.