We took 4.5 yr DD, and 12 month DS in Jan to WDW. We brought his normal Graco stroller from home, and rented one for her in the parks (We also used the rentals for our WDW trip when she was 3). Assuming you have at least two adults going, it helped to have two strollers. There were many time when she wanted to do a ride where the baby couldn't go on. One parent took her to the ride, and the other sat, pushed the baby around. Most of the time, one of us took the baby back to the room early, and the extra stroller allowed her to keep going strong with the lucky parent left behind. This is just me, but I find it a lot easier to push the rental strollers, than an umbrella.