Hi April!
I'm sure you're getting excited for your first Walt Disney World vacation! One thing that's certain is that you'll be doing a lot of walking during your trip, which can make for some tired legs for your little guy at the end of the day. Even for kids who don't normally use one, a stroller can be a lifesaver, so I'd definitely recommend having one for your son. You have a few options to consider, each with its own advantages.
The best option for you might be a stroller rental for your entire stay. There are a few Disney Featured Provides listed on the
Stroller Rentals page, all of which will drop off and pick up a stroller at your Disney Resort Hotel. Some great things about these strollers are that they're all clean, comfortable, easy to maneuver and they fold up quickly for bus transportation. I’ve found this to be the more convenient and least expensive of the two rental options when staying on property.
Strollers are also available for rent by the day while you're in the parks and at Downtown Disney. If you pre-purchase your rentals for the length of your stay, there's a small discount. For this option, keep in mind that you'll only have the stroller during your time in the park or at Downtown Disney, so if you think it would be helpful to have one for the bus stops, resorts or other locations, another stroller option might be a better choice for you.
Of course, you can also take your own stroller from home, which would be the least expensive option.
You can find more information on that
Stroller Rentals page, which will help you decide which options and prices make the most sense for your family. Wishing you a most magical FIRST vacation, April!
Beth