Wailea Highlands is the smallest gated community within the Wailea Resort, yet offering the largest home sites. With a total of 14.5 acres, there are 24 lots averaging half an acre or more. The entrance is off Kaukahi Street on the ocean-side of the Hotel Wailea. Some of the lots are extremely steep, offering phenomenal vistas of the outer islands all the way from Molokini to Lanai and the West Maui Mountains. The lower lots in Wailea Highlands are still high above the 17th fairway of the Wailea Blue Golf Course.