When we went with our kids for the first time last summer, we were only concerned about our little guy needing a stroller (he turned 4 while we were there). We brought an old umbrella stroller in the van with us. We drove down from NY (and yes, we are crazy! Crazy enough to do it again this summer!). When we arrived in Orlando and took the stroller out of the van, we discovered that this old stroller wasn't just old, it was smelly too. It had gotten mold on it EWWWWWW!! That might have explained the odor in the van. I blamed it on DH's sneakers!!
So we needed to
rent a stroller while we were there and it really worked out pretty well. I think that they have a deal where you rent it for the length of your stay and you get a discount, but we kept thinking that we'd buy one somewhere, so we didn't take advantage of the discount!! Maybe someone has some details on the stroller rental discount???
Well, we never bought a stroller while we were in Orlando! We actually ended up renting a double stroller almost every day because we found that the older two boys (then 6 and 8) took turns sitting in it duringthe day, especially towards the end of the day. The Disney strollers are very easy to push even with 2 kids in them.
There are some disadvantages we found to renting. You need to find some way to distinguish your rented Disney stroller from everyone else's rented Disney stroller. We handled that by bringing lots of extra stuff with us and hanging it all over the stroller. Also, at the end of the day, you don't have a stroller to transport your child in when you arrive back at your hotel (if you have a long walk back to your room). This wasn't so much of an issue for us, as we were staying in the Fort Wilderness cabins and just loaded everyone on our golf cart, but it's hard when your kids fall asleep on the bus on the way back!