Wailea Kai

Wailea Kai sits on fairly level ground at the north edge of Wailea, just across South Kihei Road from Keawakapu Beach. A row of beachfront homes stands between the road and the sand, but the public beach access is only a few minutes away on foot, so a morning swim is an easy habit here. Inside the gates, about 100 homes line tree-shaded streets and cul-de-sacs, and the neighborhood has its own private park and greenbelt.

This is one of Wailea's older neighborhoods. It was established around 1981, and most homes were built through the 1980s, with a few into the early 1990s, so the landscaping has had decades to fill in. Lots are on the smaller side for Wailea, most between about 7,500 and 11,000 square feet, and homes on the market lately have mostly run 1,800 to 2,800 square feet, with a few larger ones up to about 4,200. Because the ground is fairly flat, few homes have ocean views; most look out on gardens or toward the mountains. Three roads lead in: from South Kihei Road, from Kilohana Drive, and a separate entrance off Okolani Drive for the smaller section known as Little Kai.

Wailea Kai has its own homeowners association, managed by Hawaiiana Management. Dues on 2026 listings ran about $400 to $490 a month, most near $404. The neighborhood is also a member of the Wailea Community Association, so owners pay that group's semi-annual assessment too, which covers shared resort landscaping and a 24-hour patrol. The Wailea resort association lists Wailea Kai among the home communities where vacation rentals are prohibited, and Maui County treats any rental shorter than 180 days as transient. Confirm current dues and rental rules with the association before writing an offer.