Wailea Highlands is located off of Kaukahi Street by the Hotel Wailea. Although it is the smallest gated community in Wailea, the lots that are available are some of the biggest. There are 24 lots on a 14.5 acre piece of land, making each lot around half an acre or more. Since some of the lots reside on steep slopes, the views from the Wailea Highlands are extraordinary. The West Maui Mountains and the islands of Molokini and Lanai are all visible from many of the lots. The residents of Wailea Highlands enjoy the luxury of living near three of Wailea's most famous golf courses in addition to several world-class hotels.