Buying in South Maui: Top Beachfront Homes, Condos, and Luxury Resorts

Nestled on the sun-drenched southern coast of Hawaii’s second-largest island, South Maui is home to some of the most desirable real estate in the Pacific. With pristine beaches, luxurious resorts, and a selection of elegant properties ranging from condos to multi-million-dollar estates, this region is a magnet for high-end buyers. Whether you're seeking a vacation home, a permanent island retreat, or an investment property, South Maui real estate offers compelling opportunities in a setting defined by natural beauty and refined living.

Wailea is synonymous with luxury. This master-planned resort community features some of the most prestigious properties in Hawaii, including ocean-view villas, custom-built estates, and exclusive gated communities. Wailea luxury homes for sale are known for their proximity to five-star resorts like the Four Seasons and Grand Wailea, world-class golf courses, and shopping at The Shops at Wailea. Buyers are drawn to the seamless integration of upscale living and tropical tranquility that defines this coastal enclave.

Just south of Wailea lies Makena, a more secluded and ultra-luxurious counterpart. This area is known for its expansive oceanfront estates and unspoiled beaches like Big Beach (Oneloa) and Maluaka Beach. Makena real estate offers a level of privacy that appeals to celebrities and high-net-worth individuals seeking solitude without sacrificing access to upscale amenities. Homes here are rare and often come with panoramic ocean views, private beach access, and proximity to the Makena Golf & Beach Club, one of the most exclusive clubs in the state.

For buyers seeking more flexibility and a wider variety of property types, Kihei offers an energetic and diverse community. From beachfront condos to single-family homes and vacation rental-friendly developments, Kihei appeals to full-time residents, investors, and snowbirds alike. The area boasts several beaches—like Kamaole I, II, and III—that are ideal for swimming, snorkeling, and sunset watching. Maui oceanfront condos in Kihei are particularly popular for their more attainable price points compared to Wailea and Makena, while still delivering breathtaking views and direct beach access.

South Maui is renowned for its inventory of upscale condominiums that offer luxury living with the ease of lock-and-leave convenience. Properties such as Wailea Beach Villas, Polo Beach Club, and Makena Surf provide resort-style amenities including gated security, oceanfront pools, fitness centers, and concierge services. Maui oceanfront condos in these complexes are in high demand due to their strong rental potential and maintenance-free lifestyle. These properties cater to buyers who value both luxury and convenience in a beachfront setting.

Beyond individual homes and condos, South Maui is also home to private resort-residential communities that combine vacation luxury with residential perks. Developments like Andaz Residences Wailea, Ho'olei at Grand Wailea, and Wailea Point offer owners unparalleled access to world-class amenities such as spas, golf, gourmet dining, and beachfront lounges. These residences blend the indulgence of hotel living with the privacy of home ownership, attracting buyers who want a turnkey luxury experience.

South Maui real estate continues to attract strong interest from both domestic and international buyers. Low inventory in prime areas like Wailea and Makena often drives competitive bidding, especially for properties with direct beach access or unobstructed ocean views. The market remains stable with steady appreciation, supported by the area’s desirability, lifestyle appeal, and limited development space. Whether purchasing a primary home or a secondary investment, buyers can expect enduring value in this sought-after coastal region.

In addition to its real estate appeal, South Maui offers an active lifestyle centered on outdoor recreation, wellness, and community engagement. Residents enjoy access to tennis clubs, hiking trails, boating charters, and some of Maui’s finest dining experiences. Annual events like the Wailea Film Festival and Maui Whale Festival bring cultural flair to the region, while miles of sandy shoreline offer daily opportunities for beach walks, snorkeling, and paddleboarding. Living here means adopting a lifestyle that is as enriching as it is relaxing.

For those purchasing from the mainland or abroad, understanding Hawaii’s real estate regulations, property taxes, and zoning laws is crucial. South Maui properties, especially in resort areas, often fall within special management zones (SMZs) with unique permitting requirements. Working with a local real estate expert is essential to navigating these complexities, especially when considering vacation rental usage, condominium association rules, and shoreline setback regulations. Doing so ensures a smooth transaction and long-term satisfaction with your investment.

Buyers exploring Wailea luxury homes for sale or oceanfront condos in Kihei will find options suitable for both personal use and income generation. Short-term vacation rental properties are popular in designated zones, offering a source of passive income when not in use. Meanwhile, South Maui’s consistent tourism demand and appeal as a second-home destination contribute to long-term market resilience. Whether the goal is capital appreciation, rental income, or a place to unwind under the palms, South Maui represents a compelling investment opportunity.

Buying in South Maui is about more than acquiring a property—it’s about embracing a lifestyle rooted in natural beauty, relaxation, and understated luxury. From Wailea’s elite estates to Kihei’s dynamic beachfront condos and Makena’s serene hideaways, South Maui real estate offers something for every discerning buyer. With expert guidance and thoughtful planning, purchasing a home in this island paradise can be one of life’s most rewarding experiences, blending investment value with personal joy in one of the world’s most cherished locations.

If you're considering a move or investment in South Maui, Steven Moody offers unparalleled expertise in navigating this luxury market. Whether you’re exploring Wailea luxury homes for sale, Maui oceanfront condos, or a resort-style community, Steven is ready to help you find the perfect fit. Contact him today to discover the finest in South Maui real estate and take the first step toward your own slice of paradise.