I haven't done that myself but everytime I go to Canyon lake to wake-board I see groups of kiters and windsurfers, pretty much always the winds are strong but not too strong, makes it a perfect spot for beginners to practice and transition to the next level. Best to monitor winds here: http://www.wunderground.com/US/TX/Canyon_Lake.html
Equipment: I have not seen rentals, probably because winds are common but not always there, best to bring your own gear
When it come to fun in the water Canyon Lake marina is the place to go. This place has the best customer service and the friendliest staff! They rent several types of boats, we usually rent a speed boat because they're the best for waterskiing and wakeboarding. They also rent jetskies, we never did but I've seen lots of other people having loads of fun on the lake. Even swimming off the boat is incredibly nice because the water is clear and has a nice blue color.
The speedboat rental runs around $70 per hour.
Equipment: Wake-boards and water skies come with the rental boat but if you're beyond the beginner's level you might consider bringing your own gear.