October might be the spookiest month of the year, but there’s nothing creepy about fall on Maui! On the contrary, between the county fair, the Hawaii Food and Wine Festival, and Halloween celebrations, October is one of the most festive months on Maui. Plus, the sweltering summer heat is a thing of the past, with temperatures leveling out to a lovely 77 degrees. Check out the best places to stay on Maui in our October Hot Picks!

South Maui: Kihei/Wailea

Like September, the golden beaches of South Maui in October become less crowded and more laid-back. October is ideal for scoring bargains on the best places to stay on Maui like luxurious rooms at Wailea’s upscale resorts or oceanview condos in Kihei! Even though temperatures are starting to cool down, days in South Maui can be roasting. If you need a break from your Wailea pool or the beach, take a leisurely drive to the Upcountry pumpkin patch for all the fall feels.

 

Mana Kai Maui

Mana Kai Maui is a unique beachfront property in Kihei offering the best of both worlds – a resort where you can choose hotel OR condominium accommodations. Guests can opt to stay in air-conditioned hotel rooms or one-bedroom and two-bedroom condominiums with full kitchens, all situated on Keawakapu Beach in Kihei. Amenities at Mana Kai Maui are hotel-style, including daily maid service, a heated swimming pool, a deli & general store, and an on-site activity desk to assist with guests’ sightseeing excursions! Book directly with the resort for the best rate!

 

Wailea Beach Villas – Floral Gardens G102

This spacious 3-bedroom 3.5-bath residence has many unique features, including an enclosed private garden and lawn that is ideal for toddlers and young children, a private open-air outdoor grotto shower, a swing, and a private cold-splash plunge pool. This villa has more outdoor garden space than any other Wailea Beach Villa, and it truly feels like a private home within a luxury resort setting. Book directly with the management company for the best rate!

 

Wailea Ekahi Village

At Wailea Ekahi, you’ll enjoy whispering palms, miles of sandy beach, and unsurpassed sunsets on Keawakapu Beach in South Maui. Stay in a studio, 0ne-bedroom or two-bedroom unit which are continuously updated and remodeled. The resort property is gated providing a private secluded atmosphere, with 4 pools, paddle tennis, and shuffleboard to keep you busy! Remember to book directly with the owners for the best rate possible!

 

Hale Kamaole 

Nestled on the southern edge of South Kihei, Hale Kamaole is surrounded by lush tropical gardens, spacious lawns, and common areas perfect for sunset watching with new friends. These 1-3 bedroom condos are ideal for groups of all sizes: spacious with full kitchens. Just steps from Kamaole Beach III, you’ll enjoy endless beach days, excellent snorkeling, and easy access to nearby shopping, dining, and local favorites like Fred’s Mexican Cafe and Moose McGillycuddy’s. Book directly with the owners for the best rate and up-to-date availability!

 

 

Central Maui: Wailuku/Kahului

A great place to get away from the resort crowds of West Maui or South Maui is Central Maui! This region includes the area you flew into which is Kahului. A short ways up the West Maui mountains is Wailuku, a beautiful mountain oasis. The major attraction of Central Maui includes ‘Īao Valley and the ‘Īao Valley State Park. Be sure to make a reservation to visit this scenic and culturally significant area of Maui!

 

Iao Valley Inn Cottage

Nestled in the heart of the majestic Iao Valley, a secluded one-bedroom private cottage offers a tranquil escape with breathtaking views of the winding Wailuku River. Wake up to the soothing sounds of nature as you gaze out of your bedroom window onto the lush landscape that surrounds you. Enjoy the freedom of a private full kitchen, allowing you to prepare delicious meals to savor on the covered lanai or in the embrace of your own personal gazebo. Unwind in style with the added luxury of an American Whirlpool Hot Tub, providing the perfect relaxation after a day of exploring the beauty that the mountains have to offer. Book directly with the local family owners, Bob and Tamara, for the best rate!

 

 

 

West Maui: Ka’anapali/Kahana/Napili

Despite October being one of the slowest months of the year on Maui, it’s an exciting time on the West Side. The beachfront high-rise hotels in Ka’anapali play host to the Hawaii Food and Wine Festival.  From the picturesque shores of Napili to the resorts in Ka’anapali, it’s fair to say that West Maui is the place to be in October.

 

Kapalua Bay Villa 29-G4

This is your perfect fall getaway! Snag an epic deal at Kapalua Bay Villa 29-G4! Originally $499 per night, now just $199! With stunning ocean views, a private lanai for sunsets, and beautifully remodeled interiors, this serene villa offers easy access to top-rated beaches, championship golf courses, and award-winning restaurants. Plus, enjoy resort amenities like swimming pools, tennis courts, and a free shuttle service—all with no extra fees! Book directly with the property management company for the best deal!

 

Hale Napili

Discover the beauty of Napili Bay at Hale Napili, where 18 cozy condos offer a peaceful retreat right by the ocean. Choose from oceanfront or garden-view units, each featuring modern amenities like free Wi-Fi, fully equipped kitchens, and beach essentials for a stress-free stay. Relax under swaying palms, enjoy beachfront BBQs, and wake up to the sound of the waves. With easy access to tennis courts, golf, and all of Maui’s adventures, Hale Napili is your ideal getaway for relaxation and exploration this fall. Book directly with the hotel for the best rate.

 

 

East Maui: Hana

They say the Road to Hana is about the journey, not the destination. That’s partially true. But Hana is incredible—and a destination worth driving hours for. Visiting Hana is like stepping back to simpler times. We love the laid-back pace, the ocean breezes, the variety of beaches, and endless tropical fruits and flowers. If you have the time, we highly recommend staying a night or two in Hana to get a feel for Maui’s easternmost town. 

 

 

Hana Kai 

Unplug at the Hana Kai. This oceanfront condo complex offers studios and 1-2 bedroom condos where you can wake up to breathtaking sunrises and soak in views of Hana Bay’s black sands. With fully equipped kitchens and private lanais, this Hana Bay retreat is the perfect place to unwind on Maui’s magical east coast. Book direct for the best rate. 

 

Mahalo for browsing this month’s Hot Picks! We hope you find your dream accommodation for your October visit. Don’t book your accommodations through an online travel agency, and reap the benefits of personalized customer service and no added booking fees!

• 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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