Do you have a baby, toddler or child under 10? Then the answer is yes!
My best advice for traveling with little kids is to bring your own stroller. You can rent them in the parks and also at Downtown Disney (this one requires a $100 deposit) for $15/day for a single and $31/day for a double. If you pay for multiple days upfront you can get a bit of a discount. These strollers are more for toddlers and not a baby, they are a hard plastic and are similar to what you might find at your local zoo or theme park. If you are planning to rent these during your stay make sure you bring a ribbon or something that will stand out. Because they all look the same there is a chance someone might walk away with yours by mistake, if that happens just bring your receipt back to a rental location for a replacement at no extra cost. Also these strollers can’t be taken out of the park so if you are planning to park hop just show your receipt at the next park for a new rental included in the original price. There are also a handful of companies in the Orlando area that you can rent from and they will even deliver/pickup at your hotel.
If you choose to bring your own the most important thing is that it is collapsible; you will need to close it when riding on the bus, train or boat. Usually if the monorail isn’t crowded we just wheel it right on, no need to close, same with the friendship boats that go between Epcot and Hollywood Studios. We bring our own stroller for a number of reasons – cost does come into play only slightly. Most important you can use it for getting around the resort, which some are very spread out. Also the Disney strollers are not ideal for babies, they are a hard plastic so if you do rent one with a baby bring a blanket to lay under them. It was also nice for having at the airport; most airlines will allow you to gate check the stroller (check when you are checking in your bags). After going through security you can just wheel them right up to the gate and check it before boarding and when you get off it will be waiting for you. Another airport bonus, it can help cart around the luggage.
Since we have traveled both when our girls were babies and toddlers we always brought our own stroller. I like the kind that can recline back so they can nap comfortably. As they got older just an umbrella stroller was good enough – the one with an attachment shade is best to keep them out of the Florida sun. On our most recent trip we pushed a side-by-side double but it was heavy which made it hard to carry on and off the bus and it just barely fit through the doors, however, it did come in handy when the 7 year old wanted to be carried at the end of the night.
There are specific locations throughout the parks designated for stroller parking. If you leave the stroller by a ride or restaurant it will probably get moved over to this area for you. There are castmembers (Disney employees) whose sole job is to tend to these areas. They are also constantly rearranging and moving them around so your stroller may not be where you left it. Make sure you tie a ribbon, balloon or other item that will stick out. Strollers can’t be taken through the ride lines or into a majority of the restaurants. There was a rare time or two if the baby was sleeping the hostess offered to let us bring our stroller up to the table. If you have a baby I would suggest investing in a carrier for your trip since you can just wear them in the lines and even on some of the rides. Last piece of advice I would not leave anything valuable in your stroller just because things could get taken or someone may walk off with your stroller by mistake.