The 13 Best Luxury Hotels with Entertainment in Wailea (2026)

For a romantic escape in Wailea, consider Hotel Wailea, Relais & Châteaux - Adults Only, renowned for its intimate setting and breathtaking views. Alternatively, Four Seasons Resort Maui at Wailea offers indulgent amenities and exceptional dining, perfect for couples seeking luxury and comfort.

If you're looking for entertainment, Grand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort boasts an extensive array of family-friendly activities and a water park. Additionally, Wailea Beach Resort - Marriott, Maui features live music and cultural events, ensuring an enjoyable stay for guests of all ages.

For travelers seeking boutique charm without breaking the bank, Lumeria Maui, Educational Retreat Center combines wellness with scenic beauty, while Hotel Wailea, Relais & Châteaux - Adults Only offers a unique luxury experience that feels exclusive yet accessible.

Families will enjoy Fairmont Kea Lani, Maui, known for its spacious suites and kid-friendly activities, along with Grand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort, which features a fantastic water park and children's programs to keep young ones entertained.

For breathtaking ocean views, look no further than Andaz Maui at Wailea Resort - A Concept by Hyatt, offering modern elegance with panoramic scenery. Likewise, The Ritz-Carlton Maui, Kapalua provides exquisite oceanfront accommodations, making it a perfect choice for those who appreciate natural beauty.

Food enthusiasts should not miss Four Seasons Resort Maui at Wailea, featuring award-winning restaurants and gourmet experiences. Also, Montage Kapalua Bay offers fine dining with locally sourced ingredients, ensuring a delightful culinary journey during your stay.