I just bought a rental in Clermont but it is for short term rentals so probably out of your budget as I rent by the week near Disney. Not on a lake, but 30 minutes from 6 different ski schools. I decided to go that route instead of dragging the boat down every winter. $35 / set at LaPoints or Active ski, doesn't make bringing the boat worth while. I would do a search for a place 30 minutes from the different ski schools in the area
Travers, Jodi Fischer, Lapoint Ski part, Active ski, Swiss, Lucky Lowes, etc.