Looking for the coolest and the most epic and unique Airbnbs in Hawaii that will guarantee a memorable trip and create long lasting memories?!?! I mean who wouldn’t want to stay in a treehouse next to an active volcano or in a sky bubble where the stars never seemed so bright?
The Hawaiian Islands are the definition of a tropical paradise. Filled with lush rainforest, waterfalls, world class beaches and active volcanos the reasons to visit Hawaii are endless. And the best part…if you are from the United States, you don’t need a passport to visit!
Although this is list of the coolest VRBO’s & Airbnbs in Hawaii collectively, each island has its own distinct charm and character. Depending on what you want to get out of your Hawaiian vacation will depend on what island you visit.
Let’s go over the highlights and the reasons to visit each island depending on your travel style. This will make choosing the perfect Airbnb in Hawaii swift and seamless.
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For full transparency, I have sprinkled some affiliate links in this post. As an Amazon Associate I earn from qualifying purchases that gives me a small commission at no extra cost to you if you decided to make a purchase. As always, I would never recommend a product or service that I didn't truely believe in. All proceeds go to keep Jess traveling and coffee ☕️. I thank you in advance.
Many of the properties listed in this post are on multiple booking sites including VRBO, Airbnb & Booking. I linked through the site with cheapest price because it feels damn good to save a little money!
The Big Island is just that, BIG and the biggest draw to the Big Island is for volcanos and a chance to see active lava flowing. The Big Island has 2 of the world’s most active volcanos Kilauea and Maunaloa, Kilauea being the most active as you may have seen in the news it had a large eruption event in the spring of 2018.
Big Island Highlights:
- Hawaii Volcanoes National Park
- Rainbow Falls
- Manta Ray Night Dive
- Akaka Falls
- Hiking to a Green Sand Beach
Maui
Maui in my opinion is the best island. Okay I may be biased as I have called Maui home for the past decade but Maui has a little bit of each island all combined into one.
It has the nightlife of Oahu, the seclusion of Kauai and a volcano to explore like the Big Island. The biggest lure to Maui has to be its beaches, with over 120 miles of coastline finding a beach to your liking will not be a problem.
Maui Highlights:
- Driving the road to Hana
- Hiking the Pipiwai Trail
- Sunrise atop Haleakala Crater
- Black, red and white sand beaches
- Whale watch tours – Check out 15 epic things to do in Maui for more inspiration
- Molokini Crater – a great water activity on Maui
- Waimoku and Wailua Falls
- Exploring Paia Town
- Iao Valley State Park
Already planning to visit Maui? Check out the best Airbnbs in Maui for a bigger selection of stunning Airbnbs worth the splurge.
Oahu
Oahu is the most populated and visited Hawaiian Island. Home to the capital Honolulu most visitors travel to Oahu for the world famous landmarks of Waikiki, Pearl Harbor and the North Shore aka the surfing capitol of the world.
Oahu has the best nightlife and shopping compared to the other islands, making this the ideal getaway for a bachelors party or girls trip. Plus Honolulu (HNL) is an international airport and most convenient island to fly into.
Highlights of Oahu:
- Waikiki
- Exploring the North Shore – including Bonzai Pipeline, Waimea Bay, Sunset Beach.
- Diamond Head
- USS Arizona Memorial – Pearl Harbor
- Kailua Beach
- Hanauma Bay
- Stairway to Heaven
- Waimea Falls
Already planning to visit Oahu? Check out the best Airbnbs in Oahu for a bigger selection of epic Airbnbs. Or best places to stay in Oahu on a budget.
Kauai
Kauai is the fourth largest and oldest Hawaiian Island. Filled with secluded beaches, roaring waterfalls and the most dramatic landscapes, Kauai is the ultimate honeymoon destination.
Life on Kauai truly moves at a slower pace. Visitors travel here for seclusion, adventure and romance all wrapped up into one. Kauai’s biggest attractions are the Napali Coastline and consistent surf.
Highlights of Kauai:
- Hiking the Napali Coast (permits required)
- Year round surf
- Hanalei Bay
- Napali Coast from above in a helicopter
- Napali Coast by boat
- Waimea Canyon
- Wailua Falls
Lanai
Lanai is the least populated Hawaiian Island. Most people only visit Lanai on a day trip from West Maui as there is a ferry that runs 3 times a week from Lahaina town to Lanai. There are not many Airbnbs or hotels on Lanai as most who stay on Lanai opt for a luxurious, secluded stay at the Four Seasons Lanai or a camping experience on Lanai. There are still plenty of things to do in Lanai that it’s worth a visit.
Highlights of Lanai:
- Manele Bay
- Pu’u Pehe aka Sweetheart Rock
- the Cat Sanctuary
- Lanai City
- Dive at a shipwreck
- Munro Trail
Planning to visit Lanai? These are the best places to stay in Lanai.
Molokai
Molokai is home to the highest sea cliffs in the world and the longest continuous fringing reef. The most well preserved Hawaiian Island, a high percentage of its population are dependents of Native Hawaiians who continue to preserve the land and believe in what you do today impacts then next 7 generations.
A trip to Molokai would ensure an authentic and off-the-beaten path Hawaiian experience.
Highlights of Molokai:
- Papohaku Beach Park
- Visit Kalaupapa by Mule
- Halawa Valley
- Explore the Sea Cliffs by Boat
Now that you’ve read an overview of what makes each island special and unique, let’s look at some of the most epic Airbnbs in Hawaii.
Overview of the coolest VRBO’s & Airbnbs in Hawaii by island
Below I have listed the top Hawaii Airbnbs for each island. Whether you are on a romantic getaway, looking for an island adventure or family vacation, there’s a perfect Airbnb in Hawaii for everyone. Plus who wouldn’t want to stay in an epic place that will make all your friends and family jealous?
- The Coolest Big Island Airbnb – Luxury Treehouse
- The Coolest Maui Airbnb – Popolana Manini Cottage
- The Coolest Oahu Airbnb – Kai Aniani
- The Coolest Kauai Airbnb – Hale Ohana
Epic VRBO’s & Airbnbs in Hawaii
Photo provided by Airbnb
Luxury Treehouse
The coolest Big Island Airbnb
- Island: Big Island
- Location: Kona, Hawaii
- Price: $439 a night
- Highlights: Adventure, Luxury, Romance
⭐️ The coolest Airbnb in Hawaii for the Big Island.
Image waking up to the sounds of the rain with a birds eye view through the trees of an ocean view. Thats what you’ll get when you experience at stay at this luxury Treehouse on the Big Island. Located just 10 minutes outside of Kona town, it’s as if you woke up in the movie the Swiss Family Robinson, one of my favorites growing up as a kid.
This epic treehouse comes equipped with all the amenities and luxuries that you would need after a day of exploring. The full kitchen comes complete with a stove, refrigerator, water filtration system and kitchen supplies so a romantic dinner in is never a problem. Plus there’s a spacious bathroom, you won’t believe that you’re staying in a treehouse.
Enjoy a glass of wine on the lanai or in the hot tub as the sun sets on another beautiful Hawaiian day. This indoor/outdoor, tropical getaway is ideal for outdoor adventurers, honeymooners, couples or friends just looking for an unforgettable experience.
Photo provided by Airbnb
Popolana Manini Cottage
The coolest Maui Airbnb
- Island: Maui
- Location: Hana, Hawaii
- Price: $275 a night
- Highlights: Adventure, Seclusion
⭐️ The best VRBO/Airbnb in Hawaii for Maui.
The Popolana Manini Cottage is located on the gorgeous Hana Bay, this stay will allow you to experience all of the adventures that Hana has to offer. The reason this cottage made the list of best Airbnbs in Hawaii is for the location.
Hana is found on East Maui and is one of the most magical parts of Maui. Located within 5-15 minutes of this cottage are black sand beaches, hidden waterfalls, pristine coastlines and various hiking trails including my favorite hike on the island the Pipiwai Trail.
The newly renovated cottage includes one bedroom and a full bath and kitchen. There is also a 2 bedroom, 2 bath cottage next to the Manini is you are traveling with a bigger group. Make sure you rise early to watch sunrise over Hana Bay, an experience you won’t forget during your Hana trip. Paradise awaits.
Insider Tip: Check out these articles to help plan your trip to Hana.
The Best Stops on the Road to Hana
Photo provided by Airbnb
Kai aniani
The coolest Oahu Airbnb
- Island: Oahu
- Location: Waialua, Hawaii
- Price: $1,755 a night
- Highlights: Luxury, Luxury, Luxury
⭐️ The coolest Airbnb in Hawaii for Oahu.
Making the best Airbnbs in Hawaii list for the Oahu is the the Kai aniani. The Kai ainiani, also known as the Sea of Glass is luxury on the North Shore of Oahu. The Sea of Glass is an architecturally stunning beachfront home.
As soon as you see it you will understand how it got its name. The front of the home has wall-to-wall sliding glass doors which offers stunning views from every room of the house.
Designed to treat your mind, body and soul. The breathtaking view of the ocean from every single window and door is simply amazing! There are four bedrooms in each corner of the main level of the house each having its own bathroom.
This stay accommodates up to 8 people comfortably and in luxury. The vaulted ceilings and floor to ceiling windows will make your jaw instantly drop to the floor as you are greeted with tropical ocean views. From the gourmet kitchen to the stunning views, this stay is luxury at its finest.
You won’t even have to leave the property to enjoy hiking, biking, swimming, snorkeling, surfing, and kayaking some of the best things to do on the North Shore. It will be pretty hard to start packing when your stay is over.
Photo provided by Airbnb
Hale Ohana
An Epic Kauai Airbnb
- Island: Kauai
- Location: Princeville, Hawaii
- Price: $350 a night
- Highlight: North Shore of Kauai, Amenities
⭐️ The best Airbnb in Hawaii for Kauai.
Experience paradise at the Hale Ohana, a hidden gem on the North Shore of Kauai. This luxury cottage is a 2 bed, 2 bath home that can accommodate up to 4 people. The newly remodeled design and open design creates an inviting space. The space is bright, airy and charming. The top feature of this stay has to be the private plunge pool.
Located only 5 minutes away from Hanalei Bay, one of Kauai’s top sights. If you came here for seclusion, there is a secluded beach 15 minutes walking distance away. Between the location, style and amenities you can’t go wrong with this vacation rental.
Stay here for style, privacy and rejuvenation. Your peaceful, tranquil tropical getaway begins here!
More Standout VRBO’s & Airbnbs in Hawaii
Photo provided by Airbnb
Kula Star Dome
- Island: Maui
- Location: Kula, Hawaii
- Price: $295 a night
- Highlight: Star gazing
If you enjoy star gazing, you can’t get closer to the stars then a stay at the Kula Star Dome. Located at 2600 ft. elevation on the way to crater of Haleakala National Park on Maui, this is a unique Airbnb in Hawaii is a way to comfortably be able to watch the stars with an unobstructed view.
You stay in a heated, clear dome bubble hut that allows you to view the stars from the comforts of your own air bed. It does get cold at night (yes it even snows on Maui) so the skylight loft with a king bed is included with the stay if you don’t want to spend the whole night in the dome bubble.
Of course this Hawaii Airbnb comes with all the modern amenities including Wifi, breakfast, parking and coffee. This is the perfect Airbnb in Maui that offers a short drive to witness sunrise atop Haleakala and to explore Upcountry Maui.
Photo provided by Airbnb
Tiny Home on a Volcanic Lava Field
- Island: Big Island
- Location: Pāhoa, Hawaii
- Price: $175 a night
- Highlight: Unique location, off-the-grid
The Big Island is all about lava fields and volcanos. Staying at the Ohana House is a one of a kind experience on the Big Island. Situated on the Kalapana lava beds near the base of the Kilauea Volcano, this unique tiny home is surrounded by epic views of Kilauea and miles black lava fields.
Staying at this unique Hawaii Airbnb puts you in perfect location to explore nearby attractions such as the Volcanoes National Park, the Red Road, the new black sand beaches, and restaurants in nearby Pahoa.
The tiny home is surprisingly spacious as there are two pods connected by a lanai in the middle. On the left is the kitchen and dining area complete with a campfire stove and kitchenware. On the right is the sleeping/living area with a main bed, 2 bunk beds and a full size bathroom. This would be a great and memorable stay for a small family, one that you’ll never forget.
Photo provided by Airbnb
Kehena Cliff House
- Island: Big Island
- Location: Pāhoa, Hawaii
- Price: $249 a night
- Highlight: Views
One of the most unique Airbnbs in Hawaii is the Kehena Cliff House. The Kehena Cliff House is an all-concrete ocean front house nestled high on a lava sea cliff at Kehena Point on the Big Island. This unique stay can accommodate up to 6 guests but 4 comfortably and has been featured on HGTV’s Off Beat American & The Travel Channel.
Being that the Kehena Cliff House sits on a point, the Hawaii Airbnb offers unparalleled views of the coastline, The 3 story home is accessed by a spiral staircase that in the center of the home.
The upper level is the master bedroom including a lanai which is perfect for whale watching if you are here between the months of November – April, sun bathing and star gazing.
The middle level is the living and dining area and the ground floor is the second bed and bath. All the rooms have sweeping ocean views as most of the house has oversized windows.
This funky Airbnb is perfect for families, couples or solo adventurists.
Photo provided by Airbnb
Bamboo Temple
- Island: Maui
- Location: Haiku, Hawaii
- Price: $500 a night
- Highlight: Lush Rainforest, peace and serenity
Experience harmony and serenity at this epic Airbnb in Hawaii at the Bamboo Temple. Located on the North Shore of Maui tucked away in the rainforests of Haiku is this peaceful refuge. The two bedroom, one bath cabin comes with a full kitchen, large wrap-around deck and your own private hot tub to relax in after a day of exploring around.
Besides the romance and tranquil setting, this Airbnb in Maui is all about the location. If you are short on time when exploring Maui the Bamboo Temple is a perfect home base to explore all that Maui has to offer. Haiku is an ideal starting point to drive the iconic road to Hana and is only a half hour away from Paia, a charming Maui town. South Kihei is less than an hour away which contains some of Maui’s best beaches andWest Maui can be reached within an hour and a half depending on traffic.
Surrounded by lush jungle, hiking trails and waterfalls, this is the perfect stay for couples as it gives off some serious romantic vibes. Awaken your soul and gain more inspiration when you stay at the Bamboo Temple in Haiku, Maui.
Travel Planning Tips: Find out how long you should visit Maui in this 7, 10 or 14 day itinerary guide and when the best time to visit Maui is.
Photo provided by Airbnb
Dreamy Tropical Tree House
- Island: Big Island
- Location: Fern Forest, Hawaii
- Price: $300 a night
- Highlight: Eco friendly, romance
Take your Hawaiian vacation to new heights with a stay at this dreamy, tropical tree house. Nestled in the canopy on top of 15 feet stilts you ascend the stairs and through a trapdoor to enter the tree house.
The breathtaking treehouse has a wrap around lanai that allows for a 360° view of the jungle. The white linens and walls create a dreamy, cloud-like aura. This treehouse is eco friendly by using natural light, solar power and a rain water catchment. This is an off-the-grid experience without sacrificing any of the comforts of normal life.
The treehouse is about 20 miles from Hilo and 8 miles from the town of Volcano which is the closest place for restaurants and groceries. Volcanoes National Park is 10 miles away where the chances of seeing lava flowing are high. This is a perfect stay for couples seeking romance in the middle of the jungle or solo travelers looking to disconnect and recharge.
Photos provided by VRBO
Suite Van Maui
- Island: Maui
- Location: Wailuku, Hawaii
- Price: $199 a night
- Highlight: House on wheels. Stay anywhere on the island.
Van life is all the rage right now and what better way to explore Maui than in a home on wheels. The Suite Van Maui is a fully equipped van that comes with everything you need including a kitchen, a shower and a toilet!
The best part about this tiny home on wheels is how eco friendly it is. The van is solar powered and has a water filtration system on board to minimize the use of plastic bottles. The van also comes equipped cookware, beach towels, beach chairs and even a portable grill on request. Did I mention it also has WiFI?!
If you’re short on time but want to get as much exploring in as possible the Suite Van Maui is the way to go. It’s easy to drive, even on the iconic road to Hana or on the West Maui loop. Maui has several scenic campgrounds all over the island including Camp Olowalu, Waianapanapa State Park, and Hosmers Grove perfect parking over night.
This is a perfect option if you are traveling Maui on a budget. Allows you access to all the best budget friendly activities on Maui.
AND VOILA! – THOSE ARE THE most epic and coolest AIRBNBS IN Hawaii! DO YOU HAVE A FAVORITE VACATION RENTAL IN Hawaii? LET ME KNOW IN THE COMMENTS BELOW!
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