We were sitting at the airport, waiting for information about our severely delayed flight, when my heart dropped. We had planned to bring our own stroller, had packed carefully and thoroughly for our trip, and had forgotten the stroller. After my initial panic, I started looking up stroller rental on my phone and realized how cheap and easy it is to rent one. In a few minutes, I had set up the stroller to be dropped off at our hotel the following day.
We rented with Orlando
Stroller rentals, which has nice strollers and is very reasonably priced. We got a City Mini Double for $80 for the week. It was delivered to our hotel's bell station as described, and when we left, we left it with the bell station.
On the January trip, we were trying to streamline expenses so we brought our own. This we used through the airport and then gate-checked.
Your decision about what to do is probably more of a personal one, and depends a lot on what kind of stroller you already have and how upset you would be if it was damaged by the airline.
The ideal stroller for Disney is: lightweight, folds easily, folds small, has a big sun shade, under-stroller storage, reclines, is relatively narrow, is easily maneuverable, and has a comfortable ride (big wheels +/- shocks).
Our rented stroller folded easily (but not small), had a big sun shade, under-stroller storage, reclined, was narrow, and was maneuverable with a comfortable ride. So it fit most of the bill.
Our own stroller is a double umbrella one (Jeep double). I'll tell you, I love this stroller, and it's a real workhorse. It's lightweight, folds easily, folds small, reclines, is narrow, and is maneuverable. It does not have a comfortable ride, and has no under-stroller storage. The sun shades are a joke, but we do have a separate add-on shade and hang-on-the-back storage compartment.
Personally, I found either option just fine. It was nice to bring our own and be able to have the kids ride in the stroller all the way through the airport. They're five, so walking is just fine. But they're slow and always somewhat underfoot, and their voluntary use of the stroller means they're contained in a potentially busy and crowded airport.
I didn't love a few things about the City Mini - I mean, it folded easily, but was quite heavy and cumbersome to bring aboard the Disney buses. It required one whole person to carry it, so doing any of the parks as a solo parent would be difficult, while my husband had very little trouble gong solo to the parks with our lighter, smaller umbrella stroller. If you can power through the travel with the City Mini it certainly provided a more comfortable experience for parent and child during the time in the park. Once back to the hotel - it took up some serious space in the already cramped hotel room!
Finally, when renting a stroller I'd definitely recommend considering where you're staying and the source. Our stroller was NOT dropped off at our hotel ROOM as I've heard some say happens. Maybe you can arrange that, but we didn't see that anywhere. At Caribbean beach, this means a separate trip to the Custom House in the morning, which was honestly not great. Consider this when you decide when to have the stroller delivered and picked up. At other resorts this wouldn't be an issue. Also, not all stroller rental companies are "approved" by Disney, and so they may only be able to drop off with you there present to sign for it. Orlando Stroller Rental is "approved" so not an issue.
Oh, and I wouldn't consider in a million years renting a stroller from Disney unless I was absolutely desperate. You can only use them within the park, they're ridiculously expensive ($27-31 a day for a double), and they're hard plastic, uncomfortable for the kids. I kind of assume that people who did that either did not know how easy it was to set up an offsite stroller company, hadn't thought about a stroller until they got to the park and then were desperate, or just plain didn't care.
Winner: Our own stroller, just because there were no great advantages to the stroller rental and it was cheaper.
Score: September - 2, January - 4