Wailea

Wailea sets the standard for south Maui luxury, and it does so with a consistency that has made it one of the most sought-after resort destinations in Hawaii. The moment you arrive, manicured grounds, lava rock walls, and lush tropical foliage make clear you've entered a different kind of resort experience, one built around space and quiet polish rather than density. The community is anchored by a string of world-class hotels including the Four Seasons, Fairmont Kea Lani, and Andaz Maui, each fronting a stretch of calm, golden sand that ranks among Maui's finest. Three championship golf courses wind through the community, and The Shops at Wailea bring a curated collection of fine dining, boutiques, and galleries to the neighborhood's heart. Wailea Beach and the coastal walking path that connects the resort beaches offer some of the best people-watching and sunset views on the island. Gather's luxury vacation rentals in Wailea range from elegant condominiums to spacious private estates, offering an elevated home base for experiencing the very best of South Maui.