A tree-shaded esplanade curves toward a majestic lobby with an open-air waterfall pond inlaid with mosaics. A meandering network of pools leads to famed Wailea Beach. With immaculate grounds and an extensive art collection, the 40-acre Grand Wailea Resort attracts families, leisure travelers, and celebrating couples.

A majestic, open-air lobby with floor mosaics, vaulted ceilings, and a fountain courtyard leads to serene garden lawns with flowering trees and playful aquatic areas. Adjacent to Polo Beach, this 22-acre, Mediterranean-style resort attracts families, leisure travelers, and celebrating couples.

From an open-air lobby with ocean views, a grand staircase leads past gardens toward pools, terraces, and Wailea’s beach walk with the ocean beyond. Occupying 22 acres, Wailea Beach Marriott Resort & Spa draws families and other leisure travelers who appreciate the proximity to the famed golf courses, shops, and tennis courts of Wailea.

Avid golfers, vacationing families, and extended-stay travelers frequent these privately owned condominiums on Paipu Beach. Although it’s 5 minutes away from the bustling resorts and Shops at Wailea, the gated apartment community feels less crowded and more residential. Buildings were built in 1983 and 1993, and landscaping along walking trails from parking lots to individual units includes hibiscus, bird of paradise, red ginger, and fragrant plumeria trees.

Dense, lush tropical plants and flowers surround two- and three-story buildings, which are arrayed on a natural hillside. These gardens create privacy screens so guests enjoy peace and quiet without any sense of the community's size. With no hotel services, no manager, and no front desk, Grand Champions is focused on home-away-from-home living, rather than resort living.

Sand-colored stucco, aqua awnings, and hillside gardens create a serene Mediterranean ambience at the 10-acre Outrigger Palms. A half-mile from Wailea's shops and beach, the condominium resort is within three miles of downtown Kihei and Wailea Golf Club.

An avenue of oleander and flowering trees leads to an open-air lobby draped around a koi-pond atrium with waterfalls and streams. The Maui Prince Hotel's A-shaped structure points toward a crescent beach and Molokini Islet in the distance. Golfers, celebrating couples, families, and other leisure travelers come to the hotel for its secluded location and modern comforts.