The question on whether to use a stroller for multiples in Disney World is really based on a number of factors. But for us, it came down to the fact that our nearly four year old twins did not like being in a stroller anymore. We had an amazing double stroller, the Mountain Buggy Urban, and we put it to great use until they were about three. We also had a couple of umbrella strollers for convenience sake. However, our kids liked (and still do) to walk everywhere, including a mile long hike in Ontario’s Algonquin Park the previous summer. We knew they wouldn’t get in the umbrella strollers and we weren’t planning on schlepping the Mountain Buggy on the plane.
We also knew that the shuttle bus came right to the front door of our hotel and it is hard to get strollers on these buses. In some very large Disney resorts, they recommend a stroller just to get to and from the bus stop. We decided that we would take our chances on day one and rent a double stroller from WDW if we needed it. We didn’t. The kids did just fine! Double strollers rent for about $33 US a day (slightly less if you buy multiple days) and they all look the same. Also, some areas can’t be accessed with them and Disney cast members move them all the time. You have to mark your stroller with something easily identifiable such as a handkerchief or risk losing it.
Other options include renting a stroller from some Orlando companies that deliver and pick them up from non-Disney hotels. But you may not know exactly how good the quality of the stroller you are getting is. One suggestion in a guidebook from a parent was to buy umbrella strollers from a store in Orlando and throw them away when you are done with them. I actually don’t think this is an environmentally friendly option and may not be convenient unless you have a car, but it could be considered.