I especially like the Wailea area best due to the beautiful beaches (and in nearby Makena) as well as the shopping. You can walk to the Shops at Wailea and the beaches from the condo. You also have access to 2 beautiful pools and BBQs/ There is also a BBQ on the lanai. We have been coming to Maui each year in December, spending Christmas and New Year's for the past 8 years. There is so much to do on Maui, yet there is also a feeling of peace and quietness. This is a perfect match for the best of both worlds!
I originally came to Maui on a Timeshare presentation and considered buying a timeshare. A friend of mine, a Realtor, showed me the alternatives, and owning in Wailea was like a dream come true! I used to drive through Wailea all the time as I like the beaches here best, even when I was staying in Kanaapali, and I used to think how gorgeous it was and how much nicer the weather here is as opposed to elsewhere on the island. I love the location of the condo, too. It has an excellent private feel to it, and the views of the tops of palm trees and the ocean are fantastic! You can see the Molikini Crater all the way to Molikini from Lanai!