Hiya Evan,
Welcome to planDisney. It is never to early to start planning a
Walt Disney World Resort vacation. May is such a great time to visit as you can typically enjoy your adventure before the Florida heat and the summer crowds arrive.
While my princes are a little past the stroller age, we have debated this exact question many times. The great news is, there is a convenient
stroller rental location at each of the theme parks as well as
Disney Springs. They offer a single and double stroller option and you can rent by the day, or you can choose a length of stay rental option which provides a discount over the daily rental cost. The strollers are extremely sturdy but not always the most comfortable as they are made out of hard plastic and they do not recline. One huge advantage to renting a stroller is you do not have to wrestle with your stroller as you board
Resort Transportation. There is always a chance that they will run out of rentals, but I have to admit, we have visited even during the busiest of times and I have never personally seen them run out.
While the stroller rental option is a popular choice for some Guests, personally we preferred bringing our own stroller, especially while our children were younger. To start, your stroller will be more comfortable, especially for younger children who may nap throughout the day. You will be able to recline your stroller and your child will probably feel more at home in a stroller they are familiar with. Additionally, Disney World vacations involve a lot of walking (sometimes 10 miles a day), and this walking takes place not just at the theme parks. The
Disney Resorts Collection hotels are quite large and a stroller will be very handy when you are wandering around your hotel to enjoy the many amenities offered. Not to mention, it is a lot easier to place a sleeping prince or princess in a stroller for that end of the day walk from your Resort Transportation to your room. Trust me, this is especially true when you are also exhausted and trying to wrangle a couple of exhausted little ones. If you plan to dine at a restaurant at another Disney Resort, or perhaps take in a round of miniature golf, you will need your stroller as these locations do not offer stroller rentals. On top of all of that, if you plan on flying in to the airport, you will definitely find the stroller helpful when traveling through the airport.
Once our princes got a little older, like the 7 or 8 range, we left the stroller at home and moved to the rental option. We found they did not need the stroller for the entire day and we would simply rent one if they started to get tired and need a break from the walking. Helpful tip - be sure to tie a colorful scarf or ribbon on the handle of the stroller. It will make it much easier to spot when exiting an attraction and trying to track it down amongst the sea of strollers.
I hope this information is helpful. If I can help with any additional planning questions, please stop back and
see me.
T-T-F-N (Ta-Ta for now),
Margaret