jfe:

We just returned last month from Maui, and it was our third trip,(2 in last 2 years). I really like the Wailea area as it really is very dry and nice. Most of the large hotels in that area are very nice, including the Four Seasons mentioned above.

If you prefer condo living, I really like the area right on the "border" between Kihei and Wailea. You can enjoy the economy of a condo, and be very close to one of the nicest areas on the island(Wailea). Keawakapu Beach is gorgeous and the stretch of beach going south is fantastic. One of the nicest things about Hawaii is that all the beaches are public so you can enjoy access to all of them even those with multimillion homes lining them.
Tons of stuff to do,enjoy.

Gwix