Known for its five beautiful, crescent-shaped beaches and stellar golf courses, Wailea is a luxurious resort community in South Maui that spans 1,500 acres of land with staggering ocean views. The area’s signature beaches include Wailea Beach, named “America’s Best Beach” in 1999. The Wailea Blue, Wailea Gold and Wailea Emerald courses make up the 54 holes of championship golf. The Shops at Wailea are a destination in itself, featuring world-class restaurants and shops, along with regular entertainment programs, such as the Maui Film Festival and Whale Week. This resort community also includes distinctive condominiums and stately private homes. Drive south about 6 miles down the coast and you’ll reach Ahihi-Kinau Natural Area Reserve, which boasts a renowned snorkeling area and coastal lava field. The site has some nice hiking trails, including the Hoapili Trail, which winds its way along the coast through some shade and then strikes inland over the lava fields to Kanaio Beach 2 to 2.5 miles away.
Grand Wailea Resort Hotel and Spa
The Grand Wailea – A Waldorf Astoria Resort is the biggest — and in many ways, the grandest — hotel in Maui’s posh and popular resort community. Large-scale Botero sculptures surround its open-air lobby pavilion; impeccable gardens look plucked from the rainforest; and dazzling fountains glisten on expansive green lawns. The sheer number of features on offer here reflects the property’s lavishness. The Grand Wailea is perhaps best known for its incredible pools. Standard rooms measure a whopping 640 square feet, and have one king or two queen size beds. Suites are larger spaces with separate living and sleeping areas, though they have the same amenities as standard rooms. Napua Tower guests have access to a private lounge that serves free continental breakfast, afternoon tea, evening hors d’oeuvres, and something called “chocolate decadence”. The Grand Wailea Maui’s Canyon Activity Pool is actually nine individual pools that span six levels. The Hibiscus Pool is named for the 630,000 mosaic tiles that create gigantic hibiscus flowers on the pool floor. The water’s small waves are great for bodysurfing and paddle boarding at the beach. The southern edge of the bay has healthy reefs where sea turtles like to swim.
The Four Seasons Resort Maui at Wailea
The Four Seasons is known for family-friendliness, and its Maui resort is a prime example. Families with children make up half (if not more) of the clientele here, so parents traveling with little ones don’t feel out of place. After a multi-million-dollar renovation in 2016, rooms at the Four Seasons Resort Maui are some of the nicest in Wailea. The immaculately maintained grounds and incredible sculpture gardens also provide romantic reprieve. The Four Seasons Maui resort piles on feature after feature, offering top-notch facilities and activities along with plenty of freebies. All guest rooms and suites have large furnished outdoor balconies or patios, most with ocean views thanks to the U-shaped building. The 26 Club Floor Rooms feature the same décor and amenities as standard guest rooms, but have pricier nightly rates due to access to the club floor lounge. There are tennis courts, a putting green, and free introductory scuba lessons in the pool. The Four Seasons Resort Maui is located on a small cliff that overlooks Wailea Beach. The fountain pool is open to everyone, and feels equally family-friendly and adult-appropriate. The adults-only serenity pool is the hotel’s nicest pool, and it truly feels like a serene oasis. The Four Seasons looks out over a lovely section of the beach, which stretches over a quarter of a mile.
Fairmont Kea Lani, Maui
The 22-acre Fairmont Kea Lani ranks among Maui’s best luxury resorts. The property attracts well-off families and couples with its features geared toward both. Accommodations at The Fairmont consist of 450 suites or villas, all of which are huge. The standard One-Bedroom Suites measure 860 square feet and are larger than the Standard Rooms of the neighboring Four Seasons or Grand Wailea. The Fairmont Kea Lani is fronted by Polo Beach, one of the most private-feeling in Wailea. The calm waters are good for snorkeling, canoeing, and kayaking, but the waves aren’t generally good for surfing here. The hotel’s three well-designed, well-maintained pools provide areas for both adults and kids to enjoy. The resort’s restaurants are generally pricey, though that’s typical for Maui and Hawaii. Ko, the hotel’s open-air signature restaurant. Nick’s Fish Market is the most romantic spot on the property. Makana Market and Cafe is the newest addition. The Willow Stream Spa offers several treatment rooms (and a beachfront cabana), mud bar, hot lava stone foot bed, and Hawaiian rain showers. The resort’s 24-hour fitness center has a wide selection of Technogym cardio equipment, plus water, magazines, towels, and classes.
Hotel Wailea Maui
Hotel Wailea has 72 one-bedroom suites and 15 acres of meticulously landscaped garden grounds. Kids under the age of 16 aren’t allowed at the hotel so the property has a quiet and serene vibe that’s popular with honeymooners and couples. Besides the beaches and the almost perfect weather — rain rarely falls in this arid microclimate, and the temperature hovers around 85 degrees year round — golf and shopping are the area’s big draws. The hotel’s 72 one-bedroom suites were originally built in 1992 as member-owned condos. Since then, they’ve been completely updated into mini-luxury retreats with kitchenettes, private outdoor spaces, and full living room spaces. The nearby Wailea Beach is one of the best swimming and snorkeling beaches in Hawaii. The hotel provides a free Mercedes-Benz shuttle to the beach club with free chairs, towels, and bottled water. The Restaurant at Hotel Wailea focuses on using organic ingredients and local fish. The restaurant is only open for dinner and breakfast, which costs extra. The Cabanas is the poolside bar/restaurant where guests can order handcrafted artisanal cocktails made with simple syrups and fresh juices along with light fare in the afternoon. The fitness center is modern and spacious, with lots of natural light.
Andaz Maui at Wailea Resort
Andaz Maui at Wailea was built on 15 acres and includes private access to the sandy public beach. The Four Seasons Maui is directly next door while upscale restaurants and boutiques are about a 10-minute walk away. Andaz is one of the most modern resorts on Maui. The check-in process happens via tablets while you sit and relax with a welcome drink. Ka’ana Kitchen, Andaz’s all-day restaurant, serves an epic breakfast buffet. For bigger families, two- and three-bedroom ocean villas provide space, comfort, convenience and direct access to the pool and beach. Morimoto Maui is the resort’s fine-dining destination (book in advance) A 24-hour market stocks tasty to-go food, wine, coffee, snacks, and acai bowls. Staffers are super-friendly and accommodating, and the overall mood is a laid-back and casual, rather than formal and uptight. The resort is at the end of the Wailea coastal path, a small distance from nearby resorts.