Many considerations here, we went through the gamut of them, back in the day!
Flying non-stop, so you probably don't need a stroller in your own airport. I am assuming you have enough hands to keep one firmly on your little one, and any carry-on bag(s) you will have with you. If your airport is really large and your child may tire, bringing your own would make sense. The Orlando airport is big and amazing and if you are collecting luggugae, getting a rental car, etc, having your stroller upon landing could be a godsend.
If you are being whisked to a resort on DME, a stroller will be pretty optional here.
If you will have a car, you have a world of choice for picking up a nice little collapsible stroller. You could even check models at your hometown Wal-Mart, order, and have pickup timed for your arrival date. There are several stores which would hardly take you out of your way driving from MCO to WDW.
If you are staying on property, with no car, look for one you like on
Amazon (or any online source) and have one that is within your budget delivered to your resort.
We purchased strollers in a Kissimmee Wal-Mart on a very first trip with youngsters. Those strollers were cheap enough that we planned to leave them behind, but so nice that we took them home, and brought them back numerous times AND passed them along once they were outgrown. You will see tons of big, elaborate strollers in the parks, but when it comes time to board trams, etc, the small ones are the winners. We never had an issue navigating tighter spaces, either.
Renting can be convenient, IF your are onsite, and can have things delivered and picked up while you are not there. always pricier, and we needed to be budget conscious, so spending about $25 worked perfectly and we were happy with our choice. Stopping to rent one at a park each day is (to us) a PITA*, the most expensive and least flexible option, as you cannot take the stroller out of the park. That leaves you without at DS, around a possibly huge resort, etc.
* just another line! But, their process is quite efficient.