Hi, Ryan!
I absolutely think a
stroller is a good idea for your upcoming visit to the Walt Disney World Resort. Both my Mouseketeers had outgrown their strollers by age five, but we brought a stroller anytime we visited the theme parks and it was well worth it for them and me! The parks are big and your son's little legs will get tired especially in the Florida heat. Since he is smaller, it will also be easier to keep up with him in the crowds when he is in the stroller.
There are three options to consider when deciding to use a stroller in the parks-bring your own, rent directly from Disney or rent from an outside company (Disney recommends three private companies that offer on-site delivery or delivery to other Orlando hotels). There are pros and cons to each so it is really a personal preference. If you rent directly from Disney, you will only have a stroller in the parks and at Disney Springs. If you reserve a stroller for multiple days, you'll pick up your stroller each day near the park's entrance showing a rental receipt, and the stroller will need to be returned before leaving the theme park. If you bring your own or rent from a private company, you'll be able to use the stroller both in the parks and back at the resort. When you are in the theme parks, there is designated stroller parking outside the attractions and venues, and you'll find a Disney Cast Member there to help you if needed. It is a great place to store small items, but I would not leave anything valuable when you park the stroller to enjoy an attraction. If you decide to bring your own or rent directly from Disney, I suggest some type of rain cover. It's no fun to come back to a soaking wet stroller!
Safe travels to you and your son, Ryan! Have a magical time making precious memories!
Nancy