Grand Wailea, a Waldorf Astoria Resort (Maui)

Maui's grandest resort playground

★★★★★📍 Wailea, Maui$$$$

Opened in 1991 as perhaps the most lavish resort ever built in Hawaii, the Grand Wailea remains Maui's exclamation point: grand lobbies open to ocean air, gardens and waterways threading 40 acres, museum-grade art (Fernando Botero's bronzes preside over the lobby), and Wailea Beach — consistently ranked among America's best — along its full frontage.

The Wailea Canyon Activity Pool is the icon: 25,000 square feet of connected pools descending the hillside through slides (including a seven-story drop), a lazy river with rapids, caves, a swim-up Tarzan rope, a baby beach, and the famous water elevator lifting swimmers back to the top. Families can spend entire days without touching the ocean — though the beach's gentle entry invites everyone in. Adults retreat to the serene Hibiscus Pool, the renovated 50,000-square-foot Kilolani Spa (among the largest in Hawaii), and dining from Humuhumunukunukuapuaa (in its own lagoon) to chef-driven Ikena.

Wailea's sunny south-shore location puts golf, the Shops at Wailea, and the coastal beach path at the door, with Molokini snorkel boats minutes away. It's the definitive choice for families wanting luxury without compromise — and couples who know the adult corners. Booked directly through Waldorf Astoria/Hilton.