Wailea Luxury Vacation Rentals, Beachfront Condos & Villas

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From $3,250.00 / daily
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Wailea_Sunset_Estate

Wailea Sunset Estate*

Kihei

Beds: 4   Baths: 5.5   Sleeps: 10
From $3,250.00 / daily
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Sea_Spirit_811

Sea Spirit 811*

Wailea

Beds: 3   Baths: 4   Sleeps: 8
From $2,495.00 / daily
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Royal_Ilima_A201

Royal Ilima A201*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $2,395.00 / daily
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SeaGlass_at_Andaz_Maui_at_Wailea_Resort

SeaGlass at Andaz Maui at Wailea Resort*

Kihei

Beds: 3   Baths: 4   Sleeps: 6
From $2,195.00 / daily
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Bella_Luna_D302

Bella Luna D302*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,945.00 / daily
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Sandcastles_Suite_L509

Sandcastles Suite L509*

Kihei

Beds: 4   Baths: 3   Sleeps: 8
From $1,895.00 / daily
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Sun_Splash_C301

Sun Splash C301*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,850.00 / daily
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Coco_Palms_Pool_Villa_D101

Coco Palms Pool Villa D101*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,795.00 / daily
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Blue_Horizon_K308

Blue Horizon K308*

Kihei

Beds: 4   Baths: 3   Sleeps: 8
From $1,695.00 / daily
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Floral_Gardens_Pool_Villa_G102

Floral Gardens Pool Villa G102*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,695.00 / daily
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Sandy_Surf_K508

Sandy Surf K508*

Kihei

Beds: 3   Baths: 3   Sleeps: 6
From $1,550.00 / daily
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Bali_Hai_Pool_Villa_F102

Bali Hai Pool Villa F102*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,450.00 / daily
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Wailea_Sunset_Bungalow

Wailea Sunset Bungalow*

Kihei

Beds: 2   Baths: 1   Sleeps: 4
From $1,350.00 / daily
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Turquoise_Cove_G301

Turquoise Cove G301*

Kihei

Beds: 4   Baths: 5   Sleeps: 8
From $1,345.00 / daily
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Orient_Pacific_Suite_J505

Orient Pacific Suite J505*

Kihei

Beds: 3   Baths: 3   Sleeps: 6
From $1,295.00 / daily
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Castaway_Cove_C201

Castaway Cove C201*

Kihei

Beds: 3   Baths: 3.5   Sleeps: 6
From $1,295.00 / daily
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Wailea_Seahorse_Suite_K507

Wailea Seahorse Suite K507*

Kihei

Beds: 3   Baths: 2   Sleeps: 6
From $1,295.00 / daily
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Sea_Breeze_J405

Sea Breeze J405*

Kihei

Beds: 3   Baths: 3   Sleeps: 6
From $1,245.00 / daily
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Sunny_Surf_E301_at_Makena_Surf

Sunny Surf E301 at Makena Surf*

Kihei

Beds: 3   Baths: 3   Sleeps: 6
From $1,195.00 / daily
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Regal_Mandalay_M511

Regal Mandalay M511*

Kihei

Beds: 3   Baths: 2   Sleeps: 6
From $1,145.00 / daily
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Azure_Azul_M212

Azure Azul M212*

Kihei

Beds: 3   Baths:   Sleeps: 6
From $1,095.00 / daily
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Aqua_Lani_J305

Aqua Lani J305*

Kihei

Beds: 3   Baths: 3   Sleeps: 6
From $1,045.00 / daily
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Grand_Seascape_K407

Grand Seascape K407*

Kihei

Beds: 3   Baths: 2   Sleeps: 6

Wailea-Makena: Maui’s Most Exclusive Vacation Experience

The resort area of Wailea and the secluded community of Makena are ideally located at the foot of the majestic Haleakala volcano on Maui’s sunny southwestern coast. Relaxation and indulgence await in this breathtaking region, with its fabulous beaches and world-class dining, shopping, golf, and spas. Just a quick drive from every possible convenience and activity, this Hawaiian hideaway also provides the perfect setting for unwinding in luxury.

Each of Wailea-Makena’s stunning beaches boasts views of the islands of Kahoolawe and Lanai, the Molokini crater, the West Maui Mountains, and spectacular sunsets. Keawakapu, nearly a mile long, enables visitors to enjoy leisurely walks on golden sands. Wailea Beach offers good swimming conditions, while Palauea/White Rock offers the opportunity to snorkel with honu, or sea turtles. Visitors can also have a uniquely Hawaiian experience at Makena State Park (also known as Big Beach), where a volcanic cinder cone borders a wide expanse of soft sand about a mile and a half long.

One of the best snorkeling spots in the Hawaiian Islands, the Ahihi-Kinau Natural Area Reserve, allows visitors to see a huge variety of fish in a shallow, protected cove or venture out into deeper waters to see beautiful coral formations and more sea turtles. Just a bit farther south, an exceptional hike begins at La Perouse Bay, where lava fields meet the sea and provide glimpses of wild goats and spinner dolphins. For a less rugged stroll, visitors may wish to take the Wailea Coastal Walk, an approximately 1.5-mile path between the ocean and Wailea’s opulent resorts. Wailea is also home to three renowned golf courses and magnificent spas like Spa Grande at the Grand Wailea, The Spa at Four Seasons, and Awili Spa at Andaz Maui.

The Shops at Wailea feature an open-air setting and a full calendar of live music and hula performances. In addition to well-known shopping options like Louis Vuitton, Prada, and Tiffany & Co., the shops contain local gems like Mahina clothing boutique, SoHa home décor, and Sand People gift shop, along with art galleries like Ki’i Gallery. Dining possibilities include Tommy Bahama Restaurant and Bar, The Pint and Cork, and Lappert’s Ice Cream.

Fine dining is also available elsewhere in Wailea, in locations such as Ko and Nick’s Fishmarket in the Fairmont Kea Lani and Humble Market Kitchin (a Roy Yamaguchi restaurant) in the Wailea Beach Resort. In the Wailea Gateway Center, Monkeypod Kitchen serves distinctive dishes and what many consider the best mai tai on the island, while Pita Paradise serves fresh Mediterranean food in a lovely casual setting. Nearby Matteo’s offers excellent Italian cuisine, and Mulligans on the Blue offers authentic Irish pub fare.

Wailea’s restaurants create special prix-fixe menus during Restaurant Week each May and November. The area is also home to the Maui Film Festival every June, as well as a fireworks display every Fourth of July. Each February, the Maui Whale Festival typically takes place in the neighboring town of Kihei. And every fourth Friday of the month, Kihei also hosts a town party featuring live music, food trucks, and local arts and crafts vendors.