Disney has cut down a LOT on allowing stroller/
scooter deliveries to the resorts. I think there is only ONE(? not sure...this is worth checking...might be 2) company that is allowed to drop these items off at bell services now for you to pick up as soon as you arrive. You can MEET the delivery vehicle from other "non-disney-approved" rental companies, but that might be on THEIR schedule, not necessarily YOURS. You can also rent at stroller at MCO. Or you can drive/uber to a local rental service and get your stroller (and then have to make a stop to drop it off when you leave.) This change happened last year and I'm sure there are a LOT of blog posts out there that have not updated this information.
if you're renting a stroller, a baby jogger city mini , or city mini gt are my recommendation. We bought one JUST for our disney trip, because there were 2016 models on clearance from albeebaby and it was cheaper than renting. And we already own a bob revolution, but here's why i talked DH into getting "another stroller." (City minis and Bobs are 2 of the most common strollers available for rental.)
city mini has one-hand fold. literally just grab the strap and lift. with the bob you need both hands, and then an additional "turn" of the stroller to be able to pick it up. the city mini also folds up smaller and is lighter than a bob.
bigger canopy. the canopy on the city mini comes a lot further forward than on our bob. more shade at disney=a good thing.
recline. I feel like they both recline the same amount, but on the city mini it's just a pinch mechanism as opposed to our bob (which again, is older, and the new ones might have a different recline mechanism) that is a buckle and you have to loosen/tighten each side if you don't want it to just lay down as far as it goes.
what I like more about the bob: it's less "tippy" than the city mini if you want to hand something off the handlebar. with the city mini, it tips over backwards if there's no baby in it and you put something heavier than a few waterbottles on the handlebar (hanging a diaper bag? not so much....that would definitely need to go in the basket underneath on a city mini)
i second the suggestion to check
amazon and possibly have something shipped to your resort. OR keep an eye on your local craigslist/fb marketplace for a used one....where I live used city minis run about $100. However, on the "too much work" to bring it in the airport....when DH and I went on our trip in August we put EVERYTHING in the stroller, and put the baby in a carrier until about 15 min before they started boarding....at that point we got our gate-check tag, put our stroller in an inexpensive "stroller bag" (again, off of amazon) to basically keep the dirt off it and got ready to get on the plane. It was really only an annoyance at security because they made us fold the stroller up and send it through the metal detector. YMMV.