Top places to stay in Hawaii.
Wailea offers accommodations that range from world-renowned oceanfront resorts and luxury villas to intimate boutique retreats overlooking the Pacific, placing visitors within easy reach of golden beaches, championship golf courses, celebrated island dining, and the striking coastline of South Maui. Each area reveals a different perspective on the destination, where lava rock shorelines, tropical gardens, and crystal-clear waters create one of Hawaii's most refined resort communities.
Wailea Resort remains the destination's defining hospitality district, where the Wailea Beach Path, Wailea Beach, Ulua Beach, and The Shops at Wailea create an exceptional setting for experiencing Maui's celebrated southern coastline. Landmark accommodations including Four Seasons Resort Maui at Wailea, Grand Wailea, A Waldorf Astoria Resort, Wailea Beach Resort - Marriott, Maui, Andaz Maui at Wailea Resort, and Hotel Wailea, Relais & ChΓ’teaux surround visitors with oceanfront dining, luxury spas, championship golf, and panoramic sunset views, while neighboring Mokapu Beach and Keawakapu Beach combine calm snorkeling waters, scenic coastal walks, and elegant beachfront resorts that reveal another side of Wailea's relaxed sophistication. Beyond the shoreline, beautifully landscaped resort communities, private residences, and hillside villas overlook the Pacific with uninterrupted views toward KahoΚ»olawe, LΔnaΚ»i, and MolokaΚ»i.
As Wailea extends beyond its central resort corridor, Makena surrounds visitors with expansive beaches, lava fields, and a quieter atmosphere anchored by Makena Beach (Big Beach) and the dramatic coastline of MΔkena State Park, while nearby KΔ«hei reveals another perspective through local restaurants, neighborhood cafΓ©s, and a lively beachfront community just north of Wailea. Across South Maui, luxury oceanfront resorts, boutique adults-only retreats, private vacation villas, and elegant condominium properties provide distinctive ways to experience the island. Between iconic beachfront resorts, tranquil hillside escapes, and refined tropical accommodations, Wailea offers stays that complement every style of travel while showcasing the extraordinary beauty and timeless elegance of Maui's southern coast. Foresyte may earn a commission when you book.
Foresyte Travel's top five choices.
5. Hotel Wailea
Hotel Wailea occupies fifteen hillside acres above Maui's southern coast, physically separating the property from the large beachfront resorts that shaped the surrounding Wailea district. The hotel originated as the Diamond Resort Hawaii, built in 1992 for members of a Japanese private club during the island's late twentieth-century resort-development boom. Its architecture disperses low-rise residential structures through tropical gardens on elevated terrain overlooking the Pacific and neighboring islands. Private owners acquired the property in 2008 and subsequently transformed it into Hotel Wailea, establishing an independent adults-only hotel within a destination dominated by major international hospitality companies. Hotel Wailea represents a distinctive second life for a private-club development created during the formative expansion of modern Wailea.
4. Fairmont Kea Lani, Maui
Fairmont Kea Lani opened in 1991 on Polo Beach during the major expansion that transformed Wailea into one of Hawaii's principal resort communities. Architect Jose Luis Ezquerra conceived the property through broad white stucco forms, arches, domes, courtyards, and extensive gardens arranged along the southern Maui coastline. The development emerged within Wailea's master-planned landscape, whose origins trace to Alexander & Baldwin and Northwestern Mutual's transformation of former ranchland into resorts, golf courses, residential enclaves, and protected shoreline access. Fairmont assumed management in 2001, connecting the property with the Canadian hotel company descended from the country's historic railway-hotel tradition. Kea Lani captures the ambitious resort construction that established Wailea's architectural and hospitality character during the closing decades of the twentieth century.
3. Andaz Maui at Wailea Resort, by Hyatt
Andaz Maui at Wailea Resort opened in 2013 on the former site of the Renaissance Wailea Beach Resort, replacing an earlier generation of development with one of Wailea's most significant twenty-first-century hotel projects. Rockwell Group shaped the interiors around basalt, timber, woven materials, and open spaces that draw the Pacific and surrounding landscape directly into the architectural composition. Tiered terraces descend toward Mokapu Beach, using the site's natural slope to organize pools, gardens, gathering spaces, and ocean views across successive elevations. The property became the first Andaz resort and an important expansion of Hyatt's design-focused brand beyond dense urban settings. Andaz Maui marks Wailea's transition from its original resort-building era into a new cycle of architectural redevelopment on already established coastal sites.
2. Grand Wailea, A Waldorf Astoria Resort
Grand Wailea opened in 1991 as the Grand Hyatt Wailea, created by Japanese developer Takeshi Sekiguchi during an extraordinary period of investment in Maui's resort economy. Architect Joel Bergman designed a vast oceanfront complex organized around grand public spaces, extensive gardens, water features, and an elaborate network of pools descending toward Wailea Beach. The property later operated under the Grand Wailea name before joining Hilton's Waldorf Astoria portfolio, carrying its original scale into successive eras of ownership and management. A major twenty-first-century transformation reworked substantial portions of the resort while preserving the physical structure established during Wailea's formative expansion. Grand Wailea captures the scale and capital intensity of the late twentieth-century development boom that permanently changed Maui's southern shoreline.
1. Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea opened in 1990 as the first Four Seasons resort, establishing a format that became central to the company's subsequent expansion into leisure destinations around the world. The property emerged during the defining development phase of Wailea, the master-planned community created across former ranchland on Maui's dry southwestern coast. Its low-rise buildings curve around landscaped grounds descending toward Wailea Beach, integrating the hotel into a coastal plan governed by setbacks, public shoreline access, and extensive open space. The resort's success helped demonstrate that Four Seasons' urban service model could translate to large destination properties, preceding the company's later resort expansion across Hawaii, the Caribbean, Mexico, and Asia. Four Seasons Maui occupies a pivotal place in both Wailea's development and the international evolution of the Four Seasons brand.
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