Road with Jacaranda tree blooming with purple flowers in Maui, Hawaii.

May Hot Picks: Where to Stay on Maui

May on Maui — is there anything sweeter? May is kicked off by Lei Day, a statewide celebration of making and giving lei, while fragrant purple jacarandas begin to bloom Upcountry. The temperatures haven’t reached their summertime peak, nor have the crowds. Below, we’ve uncovered some of the best deals and loveliest properties available for the month of May. Read on to discover our Hot Picks. 


Wailea Beach

South Maui: Kihei/Wailea

South Maui is known for fun and sun. This area receives less than 10 inches of rainfall annually, making beach days in South Maui possible almost every day. And with miles of golden beaches, it won’t be hard to find an ideal strip of sand to laze on. In addition to the wealth of ocean activities, one of South Maui‘s top attractions is Maui Brewing Company — the largest craft brewery in the state. Take a brewery tour, or sample Maui Brewing’s award-winning beers alongside dozens of other craft breweries at the Maui Brewers Festival, held every May at the Maui Arts and Cultural Center. The bi-annual Wailea Restaurant Week also takes place in May, making it an excellent month for foodies on Maui.  


Wailea Ekolu 404Wailea Ekolu 404

Wailea Ekolu 404 is a gorgeous 2-bedroom 2-bath unit in luxurious Wailea. As you walk into the living room of this beautifully remodeled condo, the sweeping view of the ocean will take your breath away.  You can enjoy awesome sunsets from the main lanai or the living/dining rooms. Book directly with the owner for the best deal!




Kamaole Beach Club B107 living room viewKamaole Beach Club B107

Best location in the complex! This 1-bedroom, 1-bathroom beachfront condo is designed for Maui living at its finest. Featuring an ocean view, the unit has been nicely updated in 2022, with travertine floors, crown molding, granite kitchen counters in the kitchen, stainless steel appliances and more. Open the full-length sliding doors to the lanai. Ideal for outdoor dining or just catching a sunset. Book directly with the management company for the best deal!



The Palms at Wailea 1102The Palms at Wailea 1102

The Palms at Wailea 1102 is a private, 2-bedroom 2-bath condo with exceptional ocean views spanning from Makena to Kaanapali. You’ll enjoy ocean views from all rooms, with a large private lanai for discrete sunning, dining and relaxing. Toast the end of a perfect day with a panoramic Maui sunset from your private table on the lanai! Book directly with the owner for the best deal!




Napili Bay

West Maui: Kaanapali/Napili/Kapalua

As the strong winter surf ceases and whales make their way back to Alaska, a plethora of ocean activities open up in West Maui in May. Ocean conditions allow for snorkeling almost every day, and parasailing and jet skiing are back on the table. Visiting on Mother’s Day? West Maui boasts an abundance of shopping, dining, and spa opportunities, making it ultra-easy to spoil mom. 

Elikapeka Suite Sands of Kahana-2Sands of Kahana – Elikapeka Suite

Elikapeka Suite at Sands of Kahana is a spacious 3-bedroom 2-bath condo provides spectacular views and island resort living with all the comforts of home.  Located on the beautiful western shore of Maui, you’ll have sandy beach access mere feet from our home, full views of the ocean, the island of Lanai, breathtaking sunsets, and the gorgeous West Maui Mountains. Book directly with the owners for the best rate!




The Kulakane is a low-rise West Maui condominium resort featuring one-bedroom and two-bedroom units, all situated beachfront in Honokowai. Every condo is just 50 feet from the ocean, offering fabulous 180-degree panoramic views of the sea, the offshore islands of Lanai and Molokai, and tropical sunsets. Book directly with the management company for the best rate!




Kaanapali Beach HotelKaanapali Beach Hotel

Proud to be known as “Hawai‘i’s Most Hawaiian Hotel,” Kaanapali Beach Hotel invites you to enjoy an idyllic tropical beachfront vacation while infusing Hawaiian culture, tradition, and aloha into everything they do. Kaanapali Beach Hotel’s Kealaula refurbishment project has been completed, including a total remodel of the rooms in two wings, a new oceanfront restaurant– Huihui, and an additional floor in the parking structure. The new renovated Premium rooms offer modern, upgraded features, while integrating traditional Hawaiian elements and culture into the design. Book directly with the hotel for the best rate!


Aina Nalu G101 Living RoomAina Nalu G101

This condominum offers two master suites, sleeping up to 6 people! Each bedroom has a King-size bed, a wall A/C unit and plenty of drawer space. Included in the unit is free internet, 46′ TV, full kitchen stocked with amenities, beach towels and cooler for road trips, and access to the relaxing pool area. Book directly with the management company for the best rate!




Hana Koki Beach

East Maui: Hana

As the COVID-19 pandemic has slowed and case counts have dropped below threatening levels, we are seeing more visitors traveling along the Road to Hana. This full-day excursion can be very taxing, and it is very hard to see all of what you want to see in just one day! The best way to experience Hana is to stop and stay at a condo or hotel in the area. Those are few and far between, but we have a great recommendation for you in May!

Hana Kai Oceanfront CondoHana Kai Maui

Hana Kai Maui features first-class studio, one- and two-bedroom condos set on exquisite oceanfront grounds. Many of Hana Kai Maui’s condos have panoramic oceanfront views allowing you to experience incredible sunrises and moonlit nights while turtles swim nearby in the surf. One-night stays are accepted in the ocean view and partial ocean view units (#101 – #205). Oceanfront units (#1 – #5) require a 2-night minimum stay (some exceptions apply). Book directly with the condominium for the best rate!


Whatever is drawing you to Maui this month, we hope you enjoy one of the loveliest months here on the Valley Isle. As of March, Maui and the state of Hawaii have dropped all remaining travel restrictions. To learn more, see our Visiting Maui During COVID blog. 


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Happy Travels!


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