Wailea Kialoa

Wailea Kialoa covers roughly 35 acres on the slope at the north end of Wailea, with Wailea Pualani Estates just uphill and Wailea Kai and The Palms at Wailea below. About 100 custom homes sit along quiet cul-de-sacs, and greenbelts run between sections of the neighborhood, so many backyards open onto green space instead of the house next door. Plenty of lots catch ocean and sunset views, though what you see changes a lot from one street to the next. Keawakapu Beach and the shops and restaurants of Wailea are a short drive away.

Homes here went up one at a time. The first were finished around 1988, many more followed through the mid-1990s, and custom builds and rebuilds have kept coming since, so a late 1980s original can sit next door to a home from the 2010s. Most lots run 8,000 to 12,000 square feet, with a handful of larger parcels close to 22,000, and homes generally range from about 2,000 to 4,500 square feet. Utilities are underground. The neighborhood is gated: Kikihi Street, the main road through Kialoa, is gated at Kapili Street and, per listing descriptions, at Okolani Drive, while Heleuma Place, a separate cul-de-sac of 23 homes set apart by a greenbelt, has its own gate off Wailea Alanui Drive. Security comes from the Wailea Community Association, which runs a 24-hour patrol across the whole resort.

Owners pay two sets of dues. The Kialoa association's dues were $436 a month on 2026 listings, up from $427 in 2025. The Wailea Community Association also bills a semi-annual assessment for the resort's shared landscaping, lighting, and patrol; one recent listing put that at $356. Kialoa is not a vacation rental neighborhood. The Wailea resort association's property list and several brokers report that its covenants prohibit vacation rentals, 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.