August in Wailea is the sunniest and the hottest month of the year. In August, the weather in Wailea is typically hot. Average daily high temperature in August is about 29 degrees above zero. On average, Wailea has 22 sunny, 5 partly cloudy, and 4 rainy days in August. The rains are usually light. August as well as January, February, April, and May is considered the most comfortable time to visit Wailea.