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.
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. 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. South Maui is also home to some of Maui’s best restaurants, making it an excellent place for foodies on Maui.
The 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!
Maui Sunset A409
This homey condo is the ideal setting for a tropical vacation. Maui Sunset is set on a quiet stretch of beach in central Kihei, not far from shops, restaurants, golf courses, and great snorkeling spots. Enjoy a pool, jacuzzi, BBQ grills, and an expansive lawn that offers direct beach access—and a great place to hangout and watch the sunset. Inside your condo, kick back on your private lanai and soak in the views, whip up homemade meals in the kitchen, or just enjoy the AC while escaping the tropical heat. Book direct to save on fees!
Makena Surf – Sunny Surf Villa E301
Perched in a top-floor corner at the coveted Makena Surf condo resort, Sunny Surf Villa E301 offers panoramic ocean views and luxe comfort in a sought-after beachfront location. This spacious three-bedroom penthouse overlooks Poolenalena Beach and features two private lanais. Take in sweeping coastal views and enjoy the nearby pool, hot tub, and sandy shoreline access. Inside, the villa features a newly remodeled kitchen, open great room, and stylish furnishings inspired by the colors of sand and sea. With resort amenities and easy access to Makena’s beaches and scenic coastal trails, Sunny Surf Villa E301 is an ideal retreat for travelers seeking luxury and tranquility in South Maui. Book direct for the best rate!
West Maui: Kaanapali/Napili/Kapalua
In May, strong winter surf begins to cease and whales make their way back to Alaska—opening up a plethora of ocean activities in West Maui. Calm conditions allow for snorkeling almost every day, and jetskiing and parasailing 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.
***We’re heartbroken after a devastating wildfire tore through our historic town of Lahaina on August 8, 2023, burning down 5 square miles of local homes and businesses. The rebuild will take years, and we’re monitoring the situation closely to keep our readers as best informed as possibly can. West Maui opened to responsible, mindful, and respectful visitors on October 8, 2023***
Kahana Manor 414
Make this beautiful, bright, newly-rennovated condo in Kahana your Maui home base. Located in the heart of West Maui, this 1bd, 1ba condo is just a short drive from the resort towns of Kapalua and Kaanapali, where snorkeling, activities, and restaurants abound. Or, stay local and head across the street to the sandy Kahana Beach. You’ll also have the opportunity to explore some of Maui’s best local hangouts — pubs, restaurants, and shops are downstairs and across the street from the unit. With AC, a full-kitchen, an an in-unit washer dryer, this is a comfortable, convenient home-away-from-home. Book direct!
Kulakane
Experience the magic of The Kulakane, a low-rise West Maui condominium resort featuring one-bedroom and two-bedroom units, all with an unobstructed ocean view in Honokowai. With just 50 feet separating you from the ocean, indulge in panoramic views of Lana’i, Moloka’i, and stunning sunsets from your private lanai. Each condo has a personalized touch with individually decorated units, all well-maintained with a full kitchen. Relax oceanside in the pool, take advantage of the gas grills, and stay connected with free wi-fi. Book directly to skip those commission fees!
Kapalua Bay Villas 29-G4
Experience paradise at Kapalua Bay Villa 29-G4, boasting breathtaking ocean views, a newly remodeled interior, and access to fantastic amenities. Relax on the private lanai, indulge in Hawaiian-inspired decor, and enjoy the comfort of a king-size bed and luxurious walk-in shower in this 1-bedroom 1-bathroom vacation rental. With its idyllic setting and thoughtful amenities, this condo promises a truly unforgettable Maui getaway that will leave you longing to return! Book directly with the property management company for the best rate possible!
Polynesian Shores
Discover the ultimate Maui retreat at Polynesian Shores, where oceanfront luxury meets affordability on the picturesque west side. Each condo boasts stunning views of Moloka‘i and Lana‘i from its private lanai, offering spacious living areas and well-equipped kitchens for a true home away from home experience. Immerse yourself in paradise with swaying palms, fragrant Plumeria trees, and the serene sound of waves, while turtles and humpback whales dance in the warm ocean just steps away, promising a warm aloha welcome and the freedom to set your own pace in this idyllic hideaway. Book directly 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! Happy vacationing!
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Aloha! Tiffany here. I've been blessed to call Maui home since 2011. With a background in the island's finest restaurants and hotels, guiding visitors to create unforgettable Maui memories is more than a skill I've mastered—it's a profound source of joy for me.
