Hi, Danielle!
You are smart to thinking about a future Disney Cruise Line (DCL) vacation when you're on board a Disney ship. When you book on board, you can save as much as 10 percent off your next cruise -- plus, get an on board credit and possibly a special deposit rate, too. Presently, DCL offers guests the opportunity to book a future cruise as far in advance as December 2012. In addition, you can change your cruise dates without penalty as long as you're in the prescribed time frame. The Future Bookings Desk can give you all the specifics, and you'll want to check your Personal Navigator when you're on board to find out exact times/locations of the Future Bookings Desk.
As far as the pools at the Wilderness Lodge, there is a main pool area -- Silver Creek Springs Pool with a small wading pool nearby. Plus, the "quiet" pool is the Hidden Springs Pool which is located near the Wilderness Lodge Villas. Each of the pool areas also have a couple of hot tubs, too.
Thanks for dropping by the Disney Moms Panel, and I hope you have a wonderful day and a magical vacation. Bon voyage!
Andi