When is the best time to visit Wailea, Hawaii?
You won't find a wrong time to visit Wailea, as the area experiences warm weather throughout the year. Temperatures are typically highest in August and September, when average daily highs reach 90 degrees Fahrenheit, and the area is generally coolest in December and January when high temperatures top out in the low 80s. Late spring through late fall is the dry season in Wailea, a time when the area receives very little rainfall. The area tends to be rainiest in midwinter, and January is typically the wettest month of the year.
Although Wailea is almost always one of the liveliest parts of Maui, the area is particularly popular during annual festivals. The Maui Film Festival graces the resorts of Wailea every June, attracting celebrities, locals, and visitors to the star-studded film screenings and events. In late May and early November, Restaurant Week allows Wailea's top chefs and dining establishments to showcase their most delectable creations via prix fixe menus and food-focused events.
If you're planning to visit during one of Wailea's biggest events, be sure to book your accommodations in advance. Not only will you get the best deals when you plan ahead, but you'll also secure a spot at your preferred hotel or resort.
Below is a chart of the current pricing seasonality of hotels and motels in Wailea, HI:
Wailea by Star Rating
Below are 3 charts demonstrating mean nightly cost trends by star rating class in Wailea, HI. You can use these charts to calculate the least expensive time period to stay in Wailea during the year.
What luxury hotels in Wailea, Hawaii are the best?
4 Star Average Prices: $337.85
Want to treat your group to a luxurious stay in Wailea? Book your getaway at one of the area's best resort properties.
For an upscale escape, you can't go wrong at the Palms at Wailea Maui by Outrigger. This midsize hotel offers spacious condo-style suites with garden or ocean views. Accommodations include balconies, barbecue grills, fully equipped kitchens, and plenty of space for the family to relax. Go for a swim in the pool or a soak in the hot tub, or stop by the resort's tour desk to book an adventure in Maui. With gardens, golf courses, and waterfront walking trails only minutes away, this resort has what you need for a memorable getaway.
Perched on the waterfront, Andaz Maui at Wailea Resort is one of Wailea's premier resorts. With 300 guest rooms, this large property has standard rooms, suites, and luxury villas to choose from. Relax beside the pool, soak up the sunshine on adjacent Mokapu Beach, or book a treatment at the luxurious Awili Spa. Enjoy a delectable meal at Ka'ana Kitchen, which serves island-inspired cuisine, or treat yourself to Japanese fusion at Morimoto Maui. With 15,000 square feet of event space, this resort is the ideal setting for a wedding or an upscale event.
One of the best-known resorts in the area, the Grand Wailea, a Waldorf Astoria Resort, is your destination for the ultimate Wailea getaway. This large resort has nearly 800 rooms and an impressive list of features, including private lanais, nine swimming pools with waterslides, a 50,000-square-foot spa, and six restaurants. Wailea Beach is outside the resort's front door, placing you in the heart of Wailea's gorgeous waterfront area. With 22 meeting rooms and outdoor event space that overlooks the ocean, the Grand Wailea is ideal for high-end events and gatherings.
What are the best budget-friendly hotels in Wailea, HI?
3 Star Average Prices: $232.76
Visiting the Wailea area doesn't have to break the bank. Take a look at the area's most affordable places to stay.
Book your stay at the Days Inn by Wyndham Maui Oceanfront in nearby Kihei, and you'll be slightly north of Wailea. Located a few minutes from Keawakapu Beach, this budget-friendly property offers easy access to swimming, sunset spots, and great dining. Have a meal at the hotel's Italian restaurant, enjoy a restful night's sleep, and awake to the free Daybreak Breakfast. You'll be tempted to unplug while you're here, but the hotel's free Wi-Fi makes it easy to book excursions or check in with family and friends while you're away.
Kauhale Makai - MCH offers affordably priced apartment-style accommodations north of Wailea. Whether you book a standard room, a studio, or a two-bedroom apartment, you'll appreciate the laid-back vibe and the family-friendly appeal. The private lanais make it easy to relax, and the on-site guest laundry facilities make staying fresh a breeze. With shopping, dining, golfing, tennis, and beaches only minutes away, you'll never have to venture far from your home away from home.
For a budget-friendly stay on the waterfront, set your sights on the Maui Seaside Hotel. This Central Maui hotel offers easy access to great swimming and windsurfing, and it features 180 guest rooms equipped with mini-fridges. Relax on your private lanai, take a swim in the outdoor pool, or head for the beach to soak up the sunshine.