View 35 Wailea villas from $1,000 per night

Wailea Villas From $1,000 Per Night

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About Wailea Villas
An island escape to one of our Wailea luxury rentals places you in the midst of a resort area, surrounded by near-perfection. Tropical flowers, ocean waves, golden sand and magnificent golf courses await.


Lea, the Hawaiian goddess of canoe builders, is believed to have morphed into a striking forest bird that would fly above one of Maui's extraordinary coastlines. Today, the location over which she flew is Wailea, also known as the Waters of Lea.

Things To Do

The lovely community surrounding our Wailea rentals will enthrall you with its five acclaimed crescent-shaped beaches, each providing inspiration in its natural beauty and recreational offerings. Wailea Beach is flanked by two black lava points and encompasses a vast area for swimming, whale watching, picnicking, sunning and sunset strolls. Spend the day here snorkeling at Ulua Beach and Mokapu Beach, separated by a reef. Polo Beach is ideal for romance; it's secluded and a great beach for spectators of surfing. Keawakapu Beach is a remote beach that offers privacy and plenty of photo opportunities.

Three golf courses in Wailea—Gold, Emerald and Blue—would entice anyone to take up golf. World-class golf courses that were designed by pros, offer remarkable views and preserve prehistoric lava rock walls, are just a few facets of this group of golf courses. Lush foliage, views of dormant Mt. Haleakala, plus a favorite course for women (Emerald) are yet more reasons to take advantage of golfing on Maui's sunny shores.

Wailea could easily be considered home to indulgence and culture. The resort area spas will provide the ultimate in luxurious treatments, which are enhanced by the beachside setting. The hotel lobbies and the Shops at Wailea offer wonderful local art displays. Plenty of walkways in Wailea offer self-guided opportunities to explore the native flora and fauna of the islands (for safety, walk during the day as these paths are not lit at nighttime).

Eat and Shop

While Wailea is home to upscale resort dining, you'll find plenty of spots for burgers, subs, pitas and pizza. Drive to nearby Kihei for more options. Kihei has mainstream grocery stores to pick up snacks, breakfast items and ingredients for a relaxing evening in your luxury rental and the farmers' market in Kihei is open every Tuesday and Friday.
Shops at Wailea offer upscale brands intermingled with boutiques and art galleries filled with fine local crafts. Grab a bite and watch the hula dancers or listen to Hawaiian music. Wailea Town Center is home to convenient services, including a wine store, a place to go for a fine bottle to take back to your Wailea luxury rental after a full day of activity.

Getting Around

Rent a car to drive to the other parts of Maui for additional sightseeing and to explore neighboring towns