There are two different options for this, priced very differently. At some resorts (I know the Grand Floridian is one, and I think maybe the Contemporary and the Poly), there are PhotoPass photo shoots you can book for, I think, 30 minutes. It costs ~$75 I think, and all the photos are added to your PhotoPass card. I think this option is only available if you pre-order the PhotoPass CD, but I may be wrong about that.
There is also an option through Disney Photography to do family photo shoots. These shoots use actual, trained photographers (NOT PhotoPass photographers). For this, you have your choice of theme park or resort to use as your photo backdrop. The "sitting fee" runs about $300 for an hour-long shoot. They create a website with proof images, and also mail you hard-copy proofs of all photos taken, and then you choose 20 for an album which is included in the cost. There are DVC (and possibly AP) discounts for this as well - we had it done on our honeymoon... I don't think the preview site is still live, but you can click the link in my siggy for my honeymoon trip report, I posted the link to the preview site along with the log-in name & password - you can check to see if it's still up. If you decide to go this route, PM me and I will get you the contact info to reserve the photo shoot.
