We've done four different timeshare condos with our teens, Cypress Point / Cypress Point Grand Villas / Orange Lake / Sheraton Vistana Villages, so I can only speak to these four. In reality they really had a great time at all four places, and for a trip, I'd happily stay at any of these again (I'd pick more based on deal that I could get vs. anything else). Oh and if you don't like where they put you at Orange Lake, just go back to the front desk and ask for something else closer to an ammenity you'd like. They have great customer service and did this for us when we asked. Our first place was on a golf course, so far away from everything and when we asked they gave us a different West Village place near a small pool that we really liked. If I had to pick which condo resort they liked best, I'd probably say the Sheraton Vistana Villages. They loved it that the pool was open till 1 a.m. and used it every night even after a busy theme park day when we got back late. At the other resorts, the pools closed earlier and they couldn't do this when we were at theme parks late. Our teens also play tennis (the whole family does), so the great clay tennis courts at the Vistana were a big hit. It's a treat to get clay tennis courts. Most places don't have these. All the resort, though, do have courts.
Enjoy whereever you go. I think Orlando is a great place to go with teens. I think it's even more fun at this age than when they were little -- but hey Orlando tends to bring out the kid in them.
Oh and by the way, if you do do Cypress Pointe / Cypress Pointe Grand Villas I'd grab a three bedroom rather than a two bedroom. The second bedroom is quite small and three bedrooms are plentiful and as resonable as two bedrooms at other places.