I think most strollers are pretty good...that being said, Peg Perego is supposed to be one of the best!!! (Not that I own one...too expensive).
Here's my take on a stroller for WDW.
1) Whatever you buy...get your son used to it. We rented a stroller ONE day, and my dd was so uncomfortable in it that we left the park and returned to the hotel to get hers!!!
2) Don't spend a fortune on it...remember, you are leaving it unattended frequently. Ours would often get "mystery spills" on it when we left it places. Plus, the park just gets them dirty!
Cosco is the cheapest brand made (cost wise), but it also had the "design" (fabric) that I wanted for my DD...so, it is the one we purchased. It has been a WONDERFUL stroller!! It has taken us on one trip to WDW, and three trips to
Disneyland...and, it is STILL going strong (DD is now 27 months). It does have a drink holder as well as a pretty big basket below. We bought it at
Walmart, and I do not remember what we paid, but it wasn't much!! At that rate, you don't care what the airline does to it, or if it gets spilled on, rained on or whatever other "mystery" items end up on it!! We have washed the fabric on ours several times, and it still looks great!!!
I'm sure there are a LOT of good ones out there...but, we have been very happy with this one!!
Good luck,
Beca