September Hot Picks: Best Maui Accommodations This Fall

Summer crowds all but evaporate by September, marking the slowest month of the year on Maui. Yet, aloha is in abundance- as well as breezy trades, summertime sunshine, and warm seas! Browse the Hot Picks for the best Maui accommodations this month, and make your dream vacation come true.

South Maui: Kihei/Wailea 

September is a great month to score a deal on some of the best Maui accommodations like a luxurious Wailea hotel room or homey Kihei condo. With kids back in school and most of the crowds gone by Labor Day, September is one of the quietest months in South Maui- figuratively speaking, that is. Wailea typically plays host to “Zeptember” every fall, a rockin’ tribute to Led Zeppelin that goes into the wee hours of the night at Mulligan’s. 

Ho’olei Wailea Beach

Perfect for large groups or those looking a space to spread out! Ho’olei Wailea Beach sleeps up to 10 people with 3 bedrooms and 3.5 bathrooms. Ride your private elevator up from the attached garage and soak in the floor-to-ceiling uninterrupted ocean view, with sliding glass doors to the lanai that retract into the wall, blending the interior space with the beauty of the outdoors. If you are looking for the perfect blend of a luxury home in close proximity to a luxury hotel, this is the answer to your search. Book directly with the owner for the best rate!

Pacific Shores A-204

This 2-bedroom 2-bath Kihei condo is tastefully decorated with plenty of room for your group to relax and reconnect. Pacific Shores A-204 sleeps up to 6 guests with 2 bathrooms, and includes access to the nice pool and hot tub area! You’re just steps from 2 of Maui’s famous South Maui beaches, with beach equipment provided. Book directly with the owner by calling or emailing (listed on our website) and skip the inflated Airbnb fees!

Hale Hui Kai 201

Nestled on the shores of Keawakapu Beach, Hale Hui Kai 201 is a fully remodeled 2-bed, 2-bath condo offering luxury living in a tropical oasis. With central A/C, a private lanai overlooking a lush garden, granite countertops, leather furniture, and plush linens, it’s a haven of modern elegance. Step outside to the powdery white sands and crystal-clear waters of Keawakapu Beach for swimming, paddleboarding, or simply unwinding on the uncrowded shore. The resort pool with ocean views adds to the charm. Book directly with Beach Breeze to skip the commission fees!

Maui Parkshore #416

Maui Parkshore 416 has the best location at this popular Kihei condo resort! This ocean-view, top-floor end unit has 2 bedrooms, nicely updated with maple cabinets, solid surface countertops, glass backsplash, stainless appliances, and beautiful hardwood flooring throughout. Open the full-length sliding doors to the 175-square-foot lanai (with a roller shade) and enjoy the ocean views! Rates starting at $195, there are plenty of openings in September! Book directly with the management company for the best rates!

Wailea Beach Villas L409

This exquisite 4-bedroom villa has a spectacular panoramic 4th floor ocean view and is nestled between The Grand Wailea & The Shops at Wailea. Magnificently furnished for the sophisticated traveler including a spacious Great Room with a 75″ Smart TV, baby grand piano, lovely artwork, 9′ ceilings, marble floors and three 55″ flat screen smart TV’s in the bedrooms. The full gourmet kitchen of Wailea Beach Villas L-409 is state of the art with granite counters, sub zero fridge & wine cooler, viking grill, dishwasher and more. Book directly with the management company for the best rate!

Hale Alana Estate

Nestled in Wailea, Maui, this stunning vacation home is a true tropical paradise. With three spacious bedrooms, two master suites, a private pool, and captivating ocean views from the 72-foot deck, it offers both luxury and relaxation. Whether you’re enjoying modern amenities inside or unwinding in the lush gardens, this retreat is your gateway to an unforgettable Maui experience. Book directly with Beach Breeze for the best rate!

West Maui: Kaanapali/Kahana/Napili

*** On August 8, 2023, a devastating wildfire tore through the historic town of Lahaina, burning down over 2,200 homes, 86% of which were residential, and damaging 2,700 buildings. The rebuild will take years, and we’re monitoring the situation closely to keep our readers as best informed as possibly can. West Maui is open to responsible, mindful, and respectful visitors starting October 8, 2023 ***

Forget about hours-long waits to get into Maui’s top restaurants in September. With the absence of summer crowds, September is a great time to explore, book a discounted room or activity, or snag tickets to a coveted luau with ease. And, seeing how whales and north swells won’t return for a few more months, parasailing and other ocean activities like snorkeling are on the table. See why the low season is a great time to visit in this Best Time to Visit Maui blog.

Napili Shores E236 – Aloha Ke Akua (Breath of Life)

This oceanfront 1 bed 1 bath condo with garden views is tucked away on the cooler side of West Maui in Napili. Enjoy the sound of the waves, striking views, beautiful sandy beaches, and snorkeling from Napili Shores E236.  Napili Shores is a two-story complex with old Hawaiian charm, less people, good views, and easy access to the beach. Book directly through the owner’s website for the best deal!

September visitors are onto something. We hope you’re as excited as we are to see you on the Valley Isle this fall!

• Looking for great places to stay on Maui? You’ll save by BOOKING DIRECTLY with the owners/managers of these accommodations.

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Happy Travels!

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