Unique places to stay in Maui | Coolest hidden gems

Are you looking for a one-of-a-kind accommodation for your next Maui vacation? Then this selection of unique places to stay in Maui is for you.

This is not a round-up of the best Wailea beach resorts and Kaanapali family hotels. As much as I love staying at the Four Seasons Resort Maui, the Andaz Maui, and the Montage Kapalua Bay, these are not what this article is all about. The focus is on unique stays and hidden gems that provide a memorable experience beyond the typical Maui getaway.

I hand-picked what I believe are the coolest places to stay in Maui. The result is a list of extraordinary vacation rentals and the most unique hotels in Maui for all budgets. Some are out-of-this-world luxurious, others are genuinely authentic, but even the quaintest listings in my selection still offer the level of comfort and style that I value for a vacation.

So, are you ready to discover the most unique places to stay in Maui? Then let’s dive in!

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My selection of unique Maui stays

For every unique Maui stay in this list, I have added all the essential details you need.

For vacation rentals, this includes the number of rooms, the number of persons it sleeps, the license number, the average cost per night, and parking inclusions. That way you can see at a glance if the rental is spacious enough and fits within your budget.

Every hidden gem stay in Maui on this list links out to the corresponding listing on Expedia, VRBO, or Airbnb. Simply read through the details, check the reviews, and set your preferred dates to get an exact breakdown of the costs. If you still like what you see, you can go ahead and make your online booking.

You can learn more about the best areas to stay in Maui at the end of the post or in my informative guide on where to stay in Maui.

Now, without further ado, here’s my personal selection of the most unique places to stay in Maui.

1. Unique hotel in Paia town

• Specifications: Intimate boutique hotel with a mix of garden view and ocean view rooms.
• Location of this unique Maui stay: Beachfront and in the heart of Paia town (North Shore).
• Registration: TAT #TA-169-602-4576-01 + #TA-043-828-0192-01 + #TA-108-077-2608-01 | TMK #2260020190000 + #2260020220000 + #2260020290000 | Licenses #STPH 2013/0002 + #STPH 2013/0005 + #STPH 2013/0007.
• Additional details: All rooms come with air conditioning and free parking.

The Paia Inn, established in 1927, is a delightful beachfront boutique hotel nestled on the North Shore of Maui. It offers a range of beautiful accommodations, from cozy doubles to exquisite suites, and even a luxurious beach house. Each room has its own open-air entry, adding to the unique experience.

This unique Maui hotel provides exclusive access to the stunning Paia Bay beach. Unwind on the soft sand, ride the waves on a boogie board, or venture out to explore the glistening waters in a kayak.

The onsite Vana Paia restaurant serves delicious Hawaiian-Japanese cuisine in the inn’s intimate garden, shaded by the magnificent Hau Tree. If you’re in the mood for something different, then try one of the other mouth-watering restaurants in Paia. This enchanting and lively town is also dotted with quaint shops and beautiful boutiques.

The options for outdoor exploration are virtually endless, with attractions such as Iao Valley State Park, the West Maui mountains, Upcountry Maui, Haleakala National Park, and the renowned Road to Hana within reach. Rent a bike at the Paia Inn hotel, embark on an ecotour, or explore the legendary Hana highway.

Expedia

2. Opulent waterfall house

• Specifications: 1 bedroom, 1+ bathroom, sleeps 4 people (no kids under 13 years of age).
• Location of this unique Maui stay: In Huelo, where North Maui meets East Maui.
• Registration: TAT #TA-082-926-7968-01 | TMK #290070570000 | License STPH 2017/0003 & #SUP2-20160013.
• Additional details: Comes with free onsite parking and air conditioning in some rooms.

Next on this list of unique places to stay in Maui is this slice of paradise nestled in the heart of the jungle.

The Waterfall House is the crown jewel of the private and secluded Pali Uli Gardens Eco-Retreat. It’s located on the grounds of the organic Hale Akua Garden Farm. This romantic dwelling comes with a serene garden and views of the magnificent Hanehoi Falls cascading one hundred fifty feet into a beautiful gorge.

Perched on a rainforest cliff, you will be treated to breathtaking views of Maui’s mesmerizing North Shore coast. The scenery is simply awe-inspiring. Listen to the soothing sounds of distant waves and a cascading waterfall from the comfort of your private deck.

The private poolside area is equipped with a gas barbecue, allowing you to enjoy a delicious meal while being surrounded by the lush jungle. As night falls, switch off the lights and witness a spectacular starlit sky from your private hot tub.

Inside this unique retreat, you’ll find an inviting open-concept design with elegant teak wood accents and marble floors. The focal point of the bedroom is a circular king-size bed, perfect for watching the most magical sunrises every morning. The master bathroom is equipped with a panoramic in-ground marble bathtub.

The location of this unique Maui stay will give you a headstart on the Road to Hana. The beaches and restaurants of Paia are just a short drive away.

VRBO

3. Entire floor of a Hawaiian pole home

• Specifications: 2 bedrooms, 2 bathrooms, sleeps 5 people.
• Location of this unique Maui stay: In Maui Meadows, a residential community uphill from Wailea (South Maui).
• Registration: TAT #TA-182-002-3296-01 | TMK #210170160000 | License #BBKM2020/0004.
• Additional details: It comes with air conditioning throughout and free parking.

Ocean Blue is an Ohana that comprises the entire first floor of a unique Hawaiian pole home in the convivial residential community of Maui Meadows, just uphill from Wailea. The beaches, shops, restaurants, and golf courses of this upscale resort area are just a short drive away.

Inside, you’ll find two bedrooms with Ritz-Carlton beds and high-quality linens, two bathrooms, and an open-plan kitchen and living area with a sofa bed. Wooden accents and high beam ceilings add to the Hawaiian charm. Step out through the sliding glass doors onto the private lanai equipped with a grill and comfortable seating.

Ocean Blue Ohana is nestled amidst a verdant garden and elevated at treetop level. Prepare to be mesmerized by the breathtaking panorama of the sparkling Pacific Ocean stretching as far as the eye can see. The vibrant hues of sunrise and sunset only add to the experience.

If you’re looking for a truly unique place to stay in Maui without compromising on comfort, then why not make this your home away from home?

VRBO

4. Secluded Hana Maui boutique hotel

• Specifications: 4* hotel.
• Location of this unique Maui stay: In Hana town, the destination of the Road to Hana (East Maui).
• Additional details: Self-parking is included in the $45 daily resort fee.

If you have a soft spot for Maui boutique hotels that offer a more distinctive experience, then you’ll love the Hana-Maui Resort. It’s situated in heavenly Hana, a charming rural town at the end of the famous Road to Hana. It’s worth extending your visit to Hana beyond a day trip just to experience this secluded retreat.

You’ll be captivated by the hotel’s picturesque outdoor pool, surrounded by lush tropical gardens and swaying palm trees. No better place to take in the panoramic ocean views.

To make your beach experience even more convenient, the Hana-Maui Resort operates a beach shuttle that will take you to a nearby scenic beach. However, keep in mind that snorkeling might not be possible here due to the rough conditions of the windward coast.

The Hana-Maui Resort provides a perfect home base for exploring the stunning beauty of the island’s east coast, including its lush tropical forests, enchanting waterfalls, aromatic flowers, and even a black sand beach. Its remote setting makes it one of the most unique places to stay in Hawaii.

Please keep in mind that the beautiful landscape of Maui’s Hana region is a direct result of its regular rainfall. Hana is famous for its ever-changing weather, so if you plan on staying at this hotel, it’s good to embrace the occasional light drizzle or even a refreshing downpour.

EXPEDIA

5. Luxury ranch estate with unrivaled ocean views

• Specifications: 2 bedrooms, 2 bathrooms, sleeps 4 people.
• Location of this unique Maui stay: Just below Sun Yat Sen Memorial Park & the Oprah Winfrey Estate in Keokea (Upcountry Maui).
• Registration: TAT #TA-101-081-2928-01 | TMK #220020050000 | License BBMP 2017/0006.
• Additional details: Comes with free parking. Air conditioning is not available and also unnecessary in the cooler Upcountry climate.

Next on this list of hidden gem stays in Maui is the Keokea Ranch Estate. It’s the ultimate place to immerse yourself in the serenity and tranquility that Upcountry Maui has to offer. Off-the-beaten-path yet a short drive from local restaurants and attractions.

This luxury home blends rustic contemporary design with a touch of island style. There are two master suites, located on opposite ends of the house, with the living area and kitchen in between. Two large sliding glass doors give access to the outdoor seating area, where you can soak in the surrounding beauty.

Live like a local while enjoying the comforts of your own home thanks to resort-like amenities such as luxurious linens and plush robes. High-quality finishes and top-of-the-line appliances are there to enhance your stay.

The stunning panoramic pool overlooks the most picturesque rolling green hills, where you can spot horses and goats, and unobstructed ocean views. Admire the sightlines of Lana’i, Molokini, Kahoolawe, and the majestic West Maui Mountains. When the night falls, unwind and let the stress melt away in the hot tub under a starlit sky.

VRBO

6. Cool surf cottage with surfboard fence

• Specifications: 2 bedrooms, 1 bathroom, sleeps 4 people.
• Location of this unique Maui stay: In the heart of Haiku, a relaxed town where many locals live (North Shore).
• Registration: TAT #TA-132-129-3824-01 | TMK #270090290000 | License #BBPH 2016/0004.
• Additional details: Comes with free parking.

The Haiku Surf Cottage’s playful and colorful decor will surely bring a smile to your face.

This intimate rental has been thoughtfully planned out. Inside, you’ll find a comfortable seating area, a well-equipped kitchen, two inviting bedrooms, and a bathroom with a convenient shower/tub combo. An additional outdoor shower adds a tropical touch to this unique place to stay.

Start your day off right by enjoying a cup of coffee in one of the patio chairs on the covered lanai. Alternatively, you can walk out to the backyard and grab a coffee and breakfast from the organic grocery store and coffee shop conveniently located next door.

Relax in the semi-private yard area. It’s adorned with cool murals and gated by an eye-catching surfboard fence. This splash of color is exactly what makes this space so inviting.

Located in the surfer town of Haiku, this cute cottage rental offers you a true taste of the local lifestyle. The stunning North Shore beaches, the breathtaking Road to Hana, and the rolling hills of Upcountry Maui are all just a short drive away. Adventurous guests will be delighted with the wide array of bucket list activities available in the immediate vicinity.

Note that this unique accommodation in Maui is not equipped with air conditioning. It relies on natural circulation, provided by the tradewinds, and ceiling fans.

VRBO

7. Plantation-style estate with private arboretum

• Specifications: 9 suites, 11 bathrooms, sleeps 20 people.
• Location of this unique Maui stay: In the green heart of Haiku (North Shore).
• Registration: TAT #TA-135-772-7744-01 | TMK #270030620000 | License #CP 2015/0007 + #SUP2 2015/0012
• Additional details: Comes with free parking and air conditioning (but not in the bedrooms).

Next on this list of hidden gems in Maui to stay is this stunning plantation estate. This unique place to stay is spacious enough to accommodate up to 20 guests, making it a fantastic location for a family reunion.

Haiku House was constructed in 1860 on a portion of land once owned by Hawaiian royalty, surrounded by sprawling acres of lush tropical greenery. Nestled on a hill, this magnificent estate overlooks the breathtaking expanse of the Pacific Ocean.

Step inside the grand hall that exudes the elegance of the historic plantation era. Haiku House features a screened-in sunroom, a formal dining room, a spacious living room, a library, and a well-equipped kitchen.

All nine suites are spacious, stylish, and well-appointed, and each comes with a private ensuite bathroom.

Follow the meandering garden trail to the arboretum, sink your teeth in one of the freshly picked fruits, enjoy a refreshing dip in the elegant pool, or dream away in one of the delightful rocking chairs on the lanai. Here, tranquility reigns supreme, allowing you to bask in a serene and private atmosphere.

VRBO

8. Adults-only boutique hotel with treehouse dining

• Specifications: 5* hotel.
• Location of this unique Maui stay: On the slopes of the Haleakala volcano overlooking the Wailea resort area (South Maui).
• Additional details: Both valet and self-parking are included in the $40 daily resort fee.

The only adults-only hotel on the island is one of the coolest places to stay in Maui for couples.

Its unique location on the slopes of the Haleakala volcano, away from the crowded coastal strip with its busy beach hotels, creates the most serene setting. Nestled in a lush tropical landscape, this luxurious boutique hotel offers unobstructed views of three stunning Hawaiian islands.

Immerse yourself in the beauty of nature as you start your day with a tranquil yoga session next to a soothing waterfall. After a delectable breakfast, wind down in one of the laid-back poolside cabanas or arrange for a complimentary beach transfer in a luxury vehicle.

No better place to indulge in a romantic 7-course dinner than at The Treehouse at Wailea, a private dining venue in the canopy of mango and avocado trees.

Each suite is uniquely decorated with premium designer decor and original artwork to create a truly special atmosphere. Enjoy the comfort of a separate bedroom and living area, high-quality linens, a deep soaking tub, a convenient kitchenette, and a private lanai equipped with chaise lounges and chairs.

EXPEDIA

9. Gorgeous modern farmhouse amidst nature

• Specifications: 3 bedrooms, 2 bathrooms, sleeps 6 people.
• Location: Amidst the luscious heart of Haiku (North Shore).
• Registration: TAT #TA-105-110-5280-01 | TMK #2270131940000 | License #BBPH 2021/0002 + SUP2 2020/0008.
• Additional details: It comes with free parking.

This delightful 3-bedroom home can be found in the heart of Maui’s scenic North Shore. It’s an enchanting residence that provides a sanctuary for those seeking comfort and tranquility. The unique native forest views allow guests to fully immerse themselves in the beauty of Maui.

Inside the farmhouse, you’ll discover a thoughtfully decorated living area, equipped with playful swing chairs and relaxing lounge chairs. The gourmet kitchen comes fully stocked. Upstairs, you’ll find three comfortable bedrooms and two bathrooms. This place is designed with care and attention to detail. So much so, that you’ll feel instantly at home.

The same can be said for the outside area, where a soothing jacuzzi and a cozy fire pit add to the relaxation. With a setting so serene, you’ll have a hard time leaving the premises.

This part of Maui, nestled between mountains and beaches, is home to an abundance of treasures. From amazing hiking trails to exciting rock climbing adventures, the great outdoors is right at your doorstep. The Road to Hana, with its mesmerizing waterfalls, starts just around the corner from this wonderful property.

Note that this unique Maui stay is not equipped with air conditioning: the steady island breeze provides plenty of natural circulation. The owners live in the back of the house but they prioritize their guests’ privacy so you’ll hardly notice they’re even there.

VRBO

10. Cute cottage in a scenic setting

• Specifications: 1 bedroom and 1 pull-out sofa, 1 bathroom, sleeps 4 people.
• Location: Tucked away in a mature tropical garden at the starting point of the Road to Hana (North Shore).
• Registration: TAT #TA-105-110-5280-01 | TMK #290070580000 | License #BBPH 2009/0015.
• Additional details: It comes with free parking and air conditioning.

Last on this list of hidden gem stays in Maui is this charming rural retreat. It is conveniently situated near one of the Road to Hana’s most picturesque viewpoints, yet far removed from the road, allowing you to experience complete tranquility.

The Star Cottage is part of the Huelo Point Lookout, a delightful retreat nestled in lush surroundings. You can enjoy ample privacy with only four enchanting structures scattered far apart. Guests can take a dip in the shared freeform swimming pool surrounded by a vibrant jungle landscape. Help yourself to fresh eggs and the abundance of organic fruit from the mature trees.

This adorable hideaway comes with its own private hot tub, shower, lanai, and BBQ grill. Indulge in the romance of the coconut grove from your private hammock. Inside, discover a kitchenette, a comfy seating area with a pull-out sofa, and a well-equipped bathroom. There is a cozy loft upstairs that has its own seating area and serves as a bedroom.

This unique lodging in Maui stands out from most other rentals in this rural North Shore area because it’s equipped with central air conditioning. While there isn’t a TV available, you can still enjoy internet access during your stay.

If you want to explore nearby towns, you’ll find Paia, Haiku, and Makawao just a short drive away. Additionally, Hookipa Beach Park, known as one of the island’s top spots for observing giant green sea turtles, is also within easy reach.

VRBO

Map of all the coolest places to stay in Maui

For your convenience, I created this map showing the location of all listings by listing number.

Which of these unique places to stay in Maui caught your eye?

Chances are that you’ve found your dream rental for that long-awaited Maui vacation. If not, then have a look at my other wish lists to discover even more amazing unique Maui rentals.

Also, rest assured that all unique places to stay in Maui featured in this article are operating legally with the required county permits and that all suggestions are hand-picked and thoroughly researched.

Unique stays in Maui FAQ