Hello Renae!
Welcome to planDisney! My family has been visiting the Parks since my children were babies and have used various combinations of strollers and baby carriers to make it through the Parks.
Lately, we have rented strollers directly from Walt Disney World Theme Parks and found it suited our needs perfectly. When
renting a stroller you have the option of a Daily rental or a Multi-Day (Length of Stay) rental. Make sure to keep your receipt as you will need it for getting a stroller the next day or at the next Park. Once you make your purchase on the first day at the first Park you will now only have to show your receipt to the Cast Member near the strollers and get a new one. You don't need to wait on a checkout line again! The stroller stays with you while you enjoy the Parks and will be labeled with your family name (if you choose). Strollers must be returned before you leave that Park so they cannot be taken on any of the Walt Disney World Resort
complimentary transportation options such as busses or monorails. They are just for in-park use. If you visit another Park that same day or with a Multi-Day rental on another day just head to the stroller rental location near the entrance and grab another stroller.
I find these strollers were perfectly fine to use for older toddlers and young school-aged children but they do not recline and are made of a molded plastic. There is no rain cover but the canopy does encompass the seat area pretty well. I sometimes miss the ability to travel with my stroller to the bus stop as it can be a long walk and if it's a long day a child is usually asleep. However, I plan for such situations by giving myself plenty of time to make it there. I also suggest bringing stroller hooks or fans for your stroller. They were removable and came with me when I returned the stroller but so helpful during my trip.
Another option is to rent a stroller from a third-party company such as ScooterBug or Kingdom Strollers. ScooterBug is Disney's Featured Provider which means that the stroller can be dropped off at Bell Services at your Resort Hotel without you needing to be present. You will find more traditional stroller options with recline options and other accessories that you may like. These strollers will travel with you everywhere until you return them to the vendor. Just don't forget that they
must be folded when on the bus! My tip is to practice opening and closing the stroller as you may be doing it quite often and under pressure. I'm the best stroller folder in my family and we have it down to a science when we board the bus where my husband holds everything and a kid while I fold and grab the stroller. Teamwork makes the dream work Renae!
I hope this helps and if you have any questions feel free to let me know!
Happy Planning!
-Nimmy