Cypress Pointe (both Phase I and Grand Villas) is only a couple blocks from the Crossroads intersection at Hotel Plaza Blvd. At the other end of Hotel Plaza Blvd (maybe a mile), you'll find DTD, the marketplace end (far from West Side). This is definitely a loooong walk but it does have sidewalks and crossing lights, the whole way. Cypress Pointe is a nice resort and it trades primarily through RCI. There's plenty at the resort for teens too: pools, game rooms, mini golf, basketball, shuffleboard, etc. A cab to DTD from here would be ~$10-$15 one way.
Wyndham Bonnet Creek is next door to Disney's Caribbean Beach Resort. It's an easier drive to DTD from here because there are fewer lights and no I-4/Lake Buena Vista traffic. However, there are no sidewalks to take you to DTD from here. Again, the cab fare would be similar. It does have free shuttles to the Disney parks, on an hourly schedule (less often mid-afternoon). Plenty of activity at this resort for kids and teens. Wyn BC trades through RCI only, with very limited availability.
Sheraton Vistana Resort (not Villages) is another half-mile to a mile further from the Crossroads, in the opposite direction from Cypress Pointe. This resort has tons of family-friendly, teen-friendly activities. It's much larger than the others and always has lots of teenagers around. The cab fare would be similar, I'd think, however there are not sidewalks the entire way and the walk would simply be too far, through very congested highway areas, to encourage them to walk it, IMO. SVR trades primarily though RCI and it's usually not to tough to trade into it, due to its large size. Learn more about the sections (older vs. newer) and how to make a request but know beforehand that you're not guaranteed to receive a newer unit, especially as an RCI exchanger.
The next closest RCI timeshares are well-beyond potential walking distance. Hope this helps.
Have fun, whatever you decide.
