My favorite hotel in Wailea is the Andaz. Rooms, pool and food are all great. If you are bringing your family, stay at the Wailea Marriott or Grand Wailea. My kids prefer the Marriott as they have two great waterslides. The Grand Wailea has great pools and direct access to the beach (where as the Marriott you have to walk 500+ yards from the hotel). 

The Montage is my favorite property on the entire island. If you feel like splurging, ditch the Four Seasons and stay at the Montage.