Wailea, Hawaii, is a small census-designated place (not a city or town) located on the island of Maui. It has a population of around 6,000 people and is home to the 1,500 acre Wailea Resort. While tourists may flock to the area, the residents of Wailea don’t feel overtaken. The area is ranked highly as one of the best residential private communities in the U.S., and many of the housing editions and condo complexes feature gated entries and extra ...more