As with most of Hawaii, Kihei has a fascinating history. According to legend, two cloud warriors, one from the north and one from the south, battled one another until a truce was called.   When the warriors separated, the piece of blue sky left between them was called Alanui o Lani (Highway to Heaven), and the area beneath that sky is now known as Kihei.

The battle theme seems to have carried over into local history, as Kihei, and the entire South Maui region, was the site of a fierce battle against conqueror Kamehameha in 1790.   Kamehameha burned his soldier's canoes in order to prevent them from retreating, and forced them to march to Wailuku, where they defeated the remaining Maui warriors in a final confrontation in the Iao Valley.  

The first inhabitants of Kihei were fishermen, and throughout the early 20th century, Kihei maintained a small population of fishermen and mesquite harvesters (Kiawe).  In 1932, the government tried to attract people to the area and offered 11 beach-front lots for sale, but only 6 of these were sold, and until the early 50's, land prices in Kihei were the cheapest on the island.  In the years since then, an increase in tourism has brought more permanent residents to Kihei.  The area maintains a population of about 16,000 year round, and that number tends to double during tourist season.