August in Wailea is the sunniest month of the year. In August, the weather in Wailea is typically warm. Average daily high temperature in August is about 25 degrees above zero. On average, Wailea has 22 sunny, 7 partly cloudy, 1 rainy, and 1 cloudy day in August. The rains are usually light. August as well as January, March, April, and May is considered the most comfortable time to visit Wailea.