Quick answer: Wailea is a master-planned resort community on the leeward (dry, sunny) side of South Maui, between Kihei to the north and Makena to the south. It's built around five public beaches connected by the Wailea Beach Path, three golf courses at Wailea Golf Club, and a cluster of large resort hotels. Housing is mostly HOA-governed condominiums (resort and golf-course view), with a smaller number of gated single-family communities and estate homes. It suits second-home buyers, vacation-rental investors (where a building's rules allow it), and buyers of luxury primary residences.

Where is Wailea?

Wailea sits on Maui's southwest-facing leeward coast, in South Maui, directly south of Kihei and north of Makena. Like the rest of the leeward side, it's on the dry, sunny side of the island, sheltered from the trade-wind rain that falls on Maui's windward slopes. It's roughly a 20-30 minute drive from Kahului Airport, depending on traffic and time of day.

A master-planned resort community

Wailea is a master-planned community, meaning its roads, landscaping, golf courses, resorts, and condo complexes were developed under a coordinated plan rather than growing up piecemeal. Development began in the 1970s and continued in phases over the following decades, which is why the area reads as more uniform and heavily landscaped than older Maui towns — low signage, buried utility lines in many areas, and consistent building setbacks are typical of the design standards that master-planned resort communities like Wailea use.

Beaches and the Wailea Beach Path

Wailea's coastline includes five named public beaches, running roughly north to south: Keawakapu, Mokapu, Ulua, Wailea, and Polo. All Hawaii beaches are public below the vegetation line, including the stretches that front hotels and condos. The beaches are linked by the Wailea Beach Path, a paved oceanfront walking path that runs the length of the resort corridor, connecting the beaches to the golf courses, hotels, and Wailea's shopping areas — a common route for walking, jogging, and watching sunset.

Golf at Wailea Golf Club

Wailea Golf Club operates three 18-hole courses in the community: the Gold, Emerald, and Blue courses. Many of Wailea's condo complexes and single-family neighborhoods border one of the three courses, which is part of why "golf-course view" is its own category of unit in the local resale market.

Resorts, shops, and Wailea Town Center

Wailea has one of the highest concentrations of large resort hotels on Maui, including the Grand Wailea, the Four Seasons Resort Maui at Wailea, the Fairmont Kea Lani, and the Andaz Maui at Wailea. Shopping and dining are centered on The Shops at Wailea, an open-air retail center along the beach path, and Wailea Town Center, a smaller commercial center a short distance inland that mixes local businesses with professional offices.

Housing types in Wailea

Most of Wailea's housing stock is condominiums, split loosely into oceanfront/resort-view buildings and golf-course-view buildings, nearly all governed by an HOA with its own architectural, use, and (often) rental rules. A smaller share of Wailea is gated single-family subdivisions and larger estate-lot homes, mostly on the community's upland and coastal edges, which trade more space and privacy for a longer drive to the beach path and shops.

Who Wailea tends to suit

Wailea attracts a fairly consistent set of buyer types: second-home owners who want a lock-and-leave property in a resort setting; vacation-rental investors, in the specific buildings where a complex's rules and zoning permit it; and buyers of luxury primary residences who want golf, beach access, and resort amenities as part of daily life rather than a vacation.

Practical notes before you buy

A few things worth checking before buying in Wailea, specifically because they vary building-by-building rather than holding true for the neighborhood as a whole: HOA and design standards — most complexes have their own architectural review and use rules, so read the governing documents, not just the listing; vacation-rental permissions — whether a unit can legally be rented short-term depends on that building's zoning and HOA rules and can change with county policy, so verify it for the exact unit rather than assuming from the area (see our broader guide to buying a Maui vacation rental for the tax and cost side of that question); and weather, which is generally dry and sunny year-round on this leeward coast, with Wailea typically seeing less rainfall than Maui's windward and upcountry areas.

Talk to a Hansen

The Hansen Ohana's office sits inside Wailea Town Center, in the neighborhood this guide covers. If you're weighing a purchase here, broker Clint Hansen (RB-21616) — Maui-born, 26 years in Wailea and Makena real estate — and the team can walk you through which complexes and communities fit your goals. See also our guide to working with a Wailea-based real estate team.

161 Wailea Ike Place, A-106, Wailea, Maui, HI 96753
Office: (808) 879-3667