Some babies can begin to use the stroller as early as 4 months, but make sure you choose a stroller that reclines so it can help support their head and neck when they get tired.
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While there are size limitations to the strollers allowed on property, there are no guidelines that mention a specific age limit at this time.
If your oldest will be four or older by the time your 2nd baby arrives, you may not even need (or want) a double stroller — or you may only need it on occasion. Outside of the weight capacity problem (usually 40-45 lbs per seat), most 4-year-olds are too big (height-wise) for many of these stroller seats.
Pre-schoolers (aged 3 to 4)The 180 minutes should include at least 60 minutes (1 hour) of moderate-to-vigorous intensity physical activity. Children under 5 should not be inactive for long periods, except when they're asleep.
While your little one may not use the stroller the entire time, it can be extremely helpful to have it on hand for when they need a break. If you're still not sold on the idea of bringing your own, an easy way to use a stroller only when you need it is by renting one from Disney!
My oldest is also 6-years old and I faced the same dilemma our trip earlier this year. In the end, I decided to have a stroller for him and I am so glad I did! I recommend a stroller as long as you can when visiting Walt Disney World Resort, even for children who would never consider using a stroller at home.
Travel with a Younger Elementary Schooler (ages 6-9)They'll likely remember much of the trip. They'll have stamina for a full day. Most rides are accessible to them. They're unlikely to be jaded about the Disney experience.
To answer your question, yes, you should have a stroller for your 3 and 5-year olds. Adventure-filled days in the theme parks require a LOT of walking, and little legs tire easily. In fact, during my family's most recent visit, my 8-year old even asked to rest his legs in the stroller a few times during the week.