Wailea Sunset Bungalow

Oceanfront Vintage Cottage Turned Charming Luxury Villa

Wailea

Luxury reigns in Wailea— a sprawling resort community on Maui’s south side. Wailea boasts lavish accommodations in spades, from stately vacation condos to sprawling five-star resorts. Beyond the plush digs, Wailea is home to three championship golf courses, deluxe spas, high-end shopping centers, gourmet restaurants, coveted beaches, and award-winning luaus— all conveniently tucked within a 1,500-acre area. Wailea’s recreational offerings make it easy to stay put. But venture just six miles south to the Keoneoio/Ahihi Kinau area, and you’ll find dramatic lava landscapes, hiking trails, and unmatched snorkeling. Meanwhile, the neighboring town of Kihei is a treasure trove of restaurants, bars, beaches, and nightlife.

Wailea translates to “the waters of Lea,” named after the Hawaiian goddess of canoe building. According to Hawaiian moolelo (legend), Lea would often transform into an elepaio, a native forest bird, and soar down from the Upcountry forests to admire Wailea’s coastal beauty. Today, Wailea’s stunning coastline is still a powerful allure. Visitors and residents alike flock to the area’s four crescent-shaped beaches— Mokapu, Ulua, Wailea, and Polo Beach— to snorkel, paddle, watch the sunset, or simply relax. And instead of appreciating Wailea’s beauty from above as Lea did, visitors can soak up panoramic island views on the 1.6-mile Wailea Beach Path, which connects five resorts and allows for effortless beach access.
Since Hawaii’s pre-contact era, Makena has undergone significant changes. Centuries ago, Makena was a thriving fishing village with an estimated population of 10,000 people, including prominent chiefs. However, Makena’s population began to decrease throughout the 1800s. Many people were leaving to work on whaling vessels, and deforestation up mauka exacerbated drought and famine in the area. Later, in the 1980s, tourism developments began to spring up across South Maui, and developers started to eye Big Beach as the site of a billion-dollar resort. This prompted community action to preserve Makena, which led to the creation of the area’s biggest attraction: Makena State Park. Today, visitors and residents alike come to Makena to enjoy the area’s raw, rugged natural beauty.