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On the east side of Maui, located along the slopes of Haleakala, is Wailea, a beautiful place most recognized for its Grand Wailea Resort and Spa. The city's estimated population of about 6,000 residents find that the upscale and extravagant layout of the area is perfect for a living environment. Wailea residents can benefit from complimentary services provided by local resorts. In addition to this, Wailea offers the promise of an affluent community that allows residents to find pleasure in the beauty and nature of Maui from the security of a safe neighborhood that has all of the services of any top-notch town.

A considerably pleasant feature Wailea has to offer is its landscaped roadways and underground utilities. Although it was originally built to serve clients of the upper class, residents of Wailea now also enjoy the city's orderly roads, beaches, and resources. Shops in Wailea provide Maui with one of the greatest selection of shopping centers that include local stores, as well as high end stores like Gucci and Fendi. Championship golf courses, tennis courts, and other various recreational facilities are also located nearby. Aside from that, Wailea also acts as host to the annual Maui Film Festival and the Maui Writers Conference.

Many water sports and tours in Wailea due to its perfect location on the leeward side of the island. Those sports include a fleet of ships established for the purpose of hosting snorkeling charters to the offshore island of Molokini. Other activities include whale watch cruises, bike tours in Haleakala, and a historic walking tour which begins in Wailea. Wailea residents generally enjoy the expensive feel of the city, its beauty and the amenities that it comes with. In spite of its posh exterior, residents and visitors appreciate the fact that Wailea is able to retain its island charm and sense of community.