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Wailea Vacation Packages

Indulge in Hawai’i’s high life with a stay in this beautiful coastal area known for its luxury accommodation and secluded beaches. 

Enjoy a luxury Hawaiian experience in the sheltered community of Wailea. A vacation here will exceed even the high expectations most people have for a trip to these paradise islands. Breathtaking ocean vistas, five wonderfully tranquil beaches and a selection of excellent golf courses make this part of Hawai’i a favorite with high-end holidaymakers.

Wailea is home to several luxury resorts and hotels. One look at the immediate surroundings and it’s easy to understand why these businesses have chosen his spot to offer the ultimate in indulgence and relaxation. The beaches in this area are perfect, with Wailea Beach having once even been named “America’s Best Beach.”

Spend your time here relaxing. Spend all day at the beach sunbathing, swimming or snorkeling. Which beach you choose depends on what you’re looking for. Makena Beach is the place to go for dreamlike views of a nearly untouched stretch of sand. Or, step into the calm waters at Polo Beach to explore the rich marine life of the area, undisturbed by strong waves and currents.

While away an afternoon at Wailea Golf Club, taking advantage of a rare opportunity to play some rounds amid idyllic scenery. Afterwards, unwind with a treatment at one of the extravagant local spas or carry on your sports session at Wailea Tennis Club.

Outdoorsy people of all ages and levels of ability should definitely add Makena Stables to their itinerary. View Wailea’s stunning landscapes from the back of a horse. Some rides are organized for the evening, set against the backdrop of an impossibly perfect Hawaiian sunset.

High-end dining and shopping options abound. Treat yourself to a shopping spree at the Shops at Wailea, where classic brands such as Gucci and Louis Vuitton can be found next to more affordable chain stores. Afterwards, enjoy dinner set to live music or head down to the sand to get the perfect photo of that iconic Hawaiian sunset.

From Kahului Airport, drive south across Maui’s narrowest part to reach Wailea. Within just half an hour, you’ll be closer to heaven than you thought was possible.

Wailea has hotels and other accommodations to suit both families and individuals. Via our lodging guide, visitors can compare up to 21 Wailea hotels and motels.

To fully enjoy your island vacation, consider booking a room at the Ho'olei at Grand Wailea and Wailea Beach Villas, A Destination Luxury Hotel.


Top Hotel Deals

See all 968 Hotels in Wailea
$234
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

75 Wailea Ike, Wailea
4.7
of 5, from 144 reviews
3.0 out of 5.0

Situated by the ocean, this hotel is within 1 mi (2 km) of Shops at Wailea and Wailea Beach. Ulua Beach and Ulua Beach Park are also within 1 mi (2 km).

$329
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr, Wailea
4.3
of 5, from 986 reviews
4.5 out of 5.0

Cradled against an oceanfront hillside, this expansive, low-rise Maui hotel lies a minute's walk from beaches and a quarter-mile from the Shops at Wailea; 3 golf courses are within 2 miles.

$419
Grand Wailea, A Waldorf Astoria Resort

Grand Wailea, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Wailea
4.4
of 5, from 865 reviews
4.5 out of 5.0

Set amid waterfall gardens and a meandering canyon of pools, this grand island resort is within a mile of championship golf, a tennis center, and upscale shops; Kihei Town is three miles away.

$509
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Wailea
4.8
of 5, from 458 reviews
5.0 out of 5.0

Located on Maui's sunny south shore, this resort faces the wide, crescent curve of Wailea Beach, with its sugar sands and calm waters. The Wailea Blue golf course and The Shops at Wailea are within a half-mile.

Wailea Grand Champions, A Destination Residence

Wailea Grand Champions, A Destination Residence

155 Wailea Ike Place, Wailea
4.5
of 5, from 260 reviews
3.0 out of 5.0

Located in Wailea, Maui, this condo resort is right on the Wailea Golf Club course. It is 1 mile from Mokapu Beach and Ulua Beach, and 1 mile from Wailea Beach. Polo Beach is 2 miles away.

$509
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Wailea
4.6
of 5, from 289 reviews
4.5 out of 5.0

Located in Wailea, this beachfront resort is next to a golf course and within 1 mi (2 km) of Ulua Beach and Wailea Beach. Mokapu Beach and Ulua Beach Park are also within 10 minutes.

Wailea Ekahi Village, A Destination Residence

Wailea Ekahi Village, A Destination Residence

3300 Wailea Alanui, Wailea
4.5
of 5, from 153 reviews
3.0 out of 5.0

Located in Wailea, this beachfront condo is next to a golf course and within 1 mi (2 km) of Ulua Beach and Wailea Beach. Mokapu Beach and Keawakapu Beach are also within 15 minutes.

$549
Hotel Wailea, Relais & Chateaux

Hotel Wailea, Relais & Chateaux

555 Kaukahi Street, Wailea
4.6
of 5, from 331 reviews
4.5 out of 5.0

Situated near the beach in Wailea, this spa resort is close to Wailea Blue Golf Course, Wailea Beach, and Wailea Emerald Golf Course. Also nearby are Wailea Gold Golf Course and Polo Beach.

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These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.