Unless something new has popped up in the past few months, Orlando is dry as a bone when it comes to pipes! There was once a Tinderbox at one of the outlet malls in the attractions area, but they had mostly trinkets and gifts, a few cigars, no pipes. Downtown had a newsstand style pipe shop long ago, but it disappeared years ago.
Sad that such a large, high traffic area doesn't have more to offer in pipes. If you want to travel to Polk County, our local Edward's in Lakeland still has a very decent selection of pipes and a comfy lounging area so you can hang out all day... Same goes for the Tinderbox here in Lakeland, fewer, but still decent pipes, and set up so that you can loiter for a while and enjoy your smoke!
If you do find something else in the area, do let us know!
Cheers
Walt