The disney strollers are easy to push but expensive ($15 per day) and you cannot take them out of the parks. I would recomment bringing your own, hiring one there or even buying a cheap one at wall-mart. I know some people do stroller exchanges here on the boards but I have no experience of this.
We always take our own for a couple of reasons: You have the pushchair at the airport, this is handy for naps if you have a delay at gatwick and also in orlando if you have to wait/queue for you car hire or transportation.
Also I no all pushchairs are different but ours reclines and has a nice amount of shade, I know before I go that I am not going to have to spend $$ on hiring something that offers the same as the pushchair that is sitting at home doing nothing.
Each to there own but I would take your own and spend the hiring $ on something a better (lots of disney soft toys for your DS )
Of course!! I didnt think about the airport etc!! He'll deffo need one then! Silly me!! Feel silly for asking now! As he is a bit lazy!!!!!!!!!!!!!!!!!!!!!!
Take your own especially if it's an umbrella stroller, you can take it to the gates at the airports, on the Disney buses, on the monorail, on the boats although you will need to fold it up. Also great for getting tired small children up to your room at the end of a busy park day leave them asleep for a wee while if you want to. The great thing about taking your own is that your child is used to it so less likely to get fussy when you are out and about. If it reclines it's even better. Our DS often fell asleep when he was under three on hloiday, he was all worn out after a day in the parks and we'd get him comfy and walk around and grab a coffee or a snack while he rested. He used to get out and walk about too to stretch his legs and get a better look at things. Just be aware in the theme parks staff often fold up umbrella strollers and place them somewhere else to allow more room for what I call the 'solid' strollers and easier wheelchair access for other guests. If your stroller is a popular make and model make sure you personalise it somehow so it does not get lost in the line up. We saw more that one of ours but luckily I had put green and yellow tape on the handles and down the strutts. That alone stopped three other families taking our stroller from the parks.
Make sure you remove any valuables from a changing bag and keep them on you or store them in a locker when you go into the shows and rides it pays to be vigilant.