Its development is guided by two important documents: a master plan that ostensibly ensures low density and good community planning, and the Wailea Community Association's design guidelines which claim to preserve Maui's island environment in all new building projects.

[11] Both documents are administered by the Wailea Community Association, which has long combined professional management (since 1984) and volunteer owner control of the Board of Directors (since 1999) to effectively manage the community in a customer service manner for all stakeholders: residents, hotels, commercial owners, and tourists.

Nearby are Wailea's many amenities, including restaurants, championship golf courses, tennis facilities, shopping, and beaches.

In ancient Hawaiian times natives would settle toward the mountains of Wailea where they grew sweet potatoes (uala) and would venture down to the shore to fish.

In the past two centuries cattle raising became a mainstay of the economy and led to the formation of places such as Ulupalakua Ranch.