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20 of the Coolest Airbnbs in Hawaii

Airbnbs in Hawaii Opener
Photo Courtesy of The Surf Shack
Are you on the hunt for the coolest Airbnbs in Hawaii? From treehouses to glass pyramids to yachts to luxury villas, there are dozens of stunning Airbnbs in Hawaii. Which one will you choose for your dream vacation?
Airbnb has revitalized the travel industry. Rather than having to stay in the same hotels in the same touristy cities as everyone else (like in Waikiki, for example), you can stay pretty much anywhere that you would like in the coolest of accommodations – like the 20 below.
As an added bonus, you can get a free $40 Airbnb coupon by using our code when you book!

The Coolest Airbnbs on Oahu, Hawaii

yellow and blue bus interior with bed
Photo Courtesy of Aloha, The Bus! Airbnb

Aloha, The Bus!, Haleiwa, Oahu

Finding affordable Airbnbs in Hawaii can be a bit of a struggle, but this revamped school bus is both affordable and creative. This unique Hawaii Airbnb was once a bus used in the Hawaii state public transportation system. Then, its new owners revamped it to be a spacious, beach-themed Airbnb. How much more creative can you home for the night get? It is important to note that the bus does not run. This little bus has also called dibs on an amazing location on Oahu’s North Shore in the town of Haleiwa. There’s so much to do on this breathtaking coastline from dining on delicious food from the famous food trucks and restaurants to spending time at amazing beaches to going for a few short hikes. If you’re interested, here’s our Ultimate Guide to the North Shore of Oahu.
This Airbnb sleeps up to three guests and costs $90 per night.
Find out more about this Airbnb here.

Sunset Beach Yurt, Haleiwa, Oahu

If you’re looking for a quirky, fun accommodation for your dream trip to Hawaii, this yurt might be your style. Yurts, typically used by nomadic people in countries like Mongolia or Turkey, are circular tents made of felts or skins. While small in size, this superhosted accommodation provides all the necessities and more, including air conditioning, a mini fridge, and an outdoor shower. The real highlight of this unique Airbnb is its location. Just steps away from the famous Sunset beach, you really can’t get much closer to a slice of Hawaii’s paradise.
This Airbnb sleeps up to two guests and costs $175 per night. Find out more about this Airbnb here.
beach front living room area
Photo Courtesy of Walker’s Lanikai Beach House Airbnb

Walker’s Lanikai Beach House, Kailua, Oahu

If you’re planning on exploring the island of Oahu, this Airbnb on the shores of Lanikai Beach in Kailua isn’t a bad option for a home base. As a matter of fact, this home was the first to be built on the pristine sand of Lanikai Beach in the late 1800s. But don’t worry, the house has been updated since then to include modern luxuries, like a full kitchen and Wi-Fi.
This Airbnb sleeps up to fourteen guests and costs $1,705 per night.
Find out more about this Airbnb here.
Yacht in front of Diamond Head Airbnbs in Honolulu
Photo Courtesy of Hookipa Yacht Airbnb

Hookipa Yacht, Honolulu, Oahu

There’s a good chance that you’re coming to Hawaii to experience the beautiful Pacific Ocean in every way possible. Perhaps you planned on going for a snorkel, taking a swim, doing a little kayaking, or even cage-diving with sharks. Now, you can even add staying on a yacht to this list of ocean activities.
This listing aboard the Hookipa Yacht features AC, TV, a Playstation 4, and, of course, lovely ocean views. Its superhost has lived up to expectations as well, as the vast majority of reviews rave about the accommodation.
This Airbnb sleeps up to four guests and costs $279 per night (although prices do increase if there are more than two guests).
Find out more about this Airbnb here.

The Coolest Airbnbs on the Big Island, Hawaii

lit up wooden house with pool in front
Photo Courtesy of Aolani House Airbnb

Aolani House, Holualoa, Big Island

Recently featured in the Airbnb Magazine, the Aolani House is truly something special. With a tiki torch-lined walkway, unobstructed 180-degree ocean views, a heated pool, a fantastic location just minutes from Kailua-Kona, and tasteful décor, there’s really not much more you could ask for from an accommodation. But somehow, the Aolani House has found a way to provide more than your wildest dreams. With advanced notice, this amazing accommodation can also provide a rental car, a private chef (for an additional cost), and a masseuse (also for an additional cost). Basically, it’s like heaven on earth.
This Airbnb sleeps up to eight guests and costs $750 per night.
Find out more about this Airbnb here.
Milky Way galaxy behind wooden tiny house Airbnbs in Hawaii
Photo Courtesy of Tiny House on a Volcano Airbnb

Tiny House on a Volcano, Pahoa, Big Island

There are many Airbnbs in Hawaii with prime locations but none as fantastic as that of this tiny house in Pahoa. Plus, for just $40 per night, you certainly get the bang for your buck. Pahoa is known for its frequent lava flows, so if you want to catch a glimpse of lava with your own eyes, this Airbnb is in the perfect spot. It is also just a few miles from seven black sand beaches, including the most newly-created one, Pohoiki Beach. And the excitement isn’t just limited to the daylight hours. At night, there is some amazing stargazing at this tiny house.
This Airbnb sleeps up to four guests and costs $40 per night.
Find out more about this Airbnb here.
modern treehouse filled with lights at dusk
Photo Courtesy of Kona’s First Luxury Treehouse Airbnb

Kona’s First Luxury Treehouse, Kailua-Kona, Big Island

It’s pretty much every kid’s dream to live in a treehouse, and now you can do that for a few nights in this Kona-based listing. Perched in a locally-treasured kukui nut tree, this Airbnb is truly a gem. Enjoy farm fresh eggs, get your fill of locally-grown fruit, try out the newly-added outdoor shower, or spend some time in your own private hot tub. If you can pull yourself away from this amazing dream of a home, the city of exciting Kailua-Kona is just a short drive away.
This Airbnb sleeps up to two guests and costs $398 per night.
Find out more about this Airbnb here.
treehouse surrounded by Hawaiian plants Airbnbs in Hawaii
Photo Courtesy of Dreamy Tropical Treehouse Airbnb

Dreamy Tropical Treehouse, Fern Forest, Big Island

I would be remiss to put just one of the amazing treehouses in the islands on this list of Airbnbs in Hawaii. This accommodation based on the Hilo side of the Big Island is just as magical as it is on the inside as it is on the outside. And with an average rating of 4.85 stars across all six categories, the previous bookers would agree. With little touches like an outdoor shower and a gramophone music player for iPhones, the superhost truly has thought of everything to make your stay in the Dreamy Tropical Treehouse as amazing as possible.
This Airbnb sleeps up to two guests and costs $300 per night.
Find out more about this Airbnb here.
glass dome with colorful star filled sky in the background
Photo Courtesy of Star Gazing Dome (Virgo) Airbnb

Star Gazing Dome (Virgo) on Private Ranch, Kealakekua, Big Island

If you’re an astronomy lover, this stargazing dome on a private ranch in Kealakekua is the dream Airbnb in Hawaii for you. This original getaway accommodation is fantastic both during the day and at night. While during the day, there are guava trees blossoming and wild pigs running around, at night, there is an unparalleled view of the stars.
This Airbnb sleeps up to three guests and costs $133 per night.
*Note: If the Virgo stargazing dome happens to be booked during your desired dates, the same host rents the Sagittarius dome, which is very similar.
Find out more about this Airbnb here.
glass pyramid with large bed in rainforest Airbnbs in Hawaii
Photo Courtesy of Volcano Glass Pyramid Airbnb

Volcano Glass Pyramid, Volcano, Big Island

While glass domes can be found in quite a few places around the world, glass pyramids are much rarer. Located on the slopes of the inactive Mauna Loa volcano, this eco-friendly, superhosted Airbnb is quite the treat. The glass walls and ceiling of this accommodation makes for amazing views of both the star-filled sky and the surrounding rainforest.
This Airbnb sleeps up to two guests and costs $150 per night.
Find out more about this Airbnb here.
limes on a tree
Photo Courtesy of Always in Season Farmstead Suite Airbnb

Always in Season Farmstead Suite, Hawi, Big Island

While most Airbnbs in Hawaii offer the typical amenities of WiFi and air conditioning, the “Always in Season Farmstead Suite” offers something a little bit different. Located on a farm, the lovely superhosts of this Airbnb allow their guests to harvest whatever they would like from their orchard and eat it. Imagine just sitting around the glass dining table, looking at a view of the sunset, while munching on some freshly-picked mangoes and pineapples. Sounds like dream, right?
As an added bonus, there are also a few tours on the property that you are encouraged to take part in.
This Airbnb sleeps up to two guests and costs $160 per night.
Find out more about this Airbnb here.
three little cabins facing the ocean Airbnbs in Hawaii
Photo Courtesy of Kulaniapa Farms Ocean View Cabins Airbnb

Kulaniapa Farms Ocean View Cabin, Hilo, Big Island

Kulaniapa Farms Ocean View Cabins are one of my favorite Airbnbs in Hawaii as they have a stunning 120-foot private waterfall in the backyard (and I’m obsessed with waterfalls)! In addition to having a little cozy cabin with amazing views all to yourself, you’ll also be able to take part in Kulaniapa Farms’ Adventure Company tours, such as waterfall rappelling, lava searching, and stargazing (for an additional price, of course). Oh, and we can’t forget to mention the stunning views of the Pacific Ocean that you can catch from your cabins.
This Airbnb sleeps up to three guests and costs $89 per night.
Find out more about this Airbnb here.
bright red cacao pods
Photo Courtesy of Hamakua Chocolate Farm Airbnb

Hamakua Chocolate Farm, Papaikou, Big Island

There are quite a few farm Airbnbs in Hawaii. However, the best may be the one at the Hamakua Chocolate Farm. Pretty much everyone loves chocolate, so imagine the joy of staying at a chocolate farm! Complete with cacao-inspired décor and sociable superhosts, this Airbnb is stocked with everything you need to have a chocolate-filled vacation. Enjoy chocolate farm tours, chocolate tastings, or simply some chocolate bars – all for an extra fee, of course.
This Airbnb sleeps up to two guests and costs $159 per night.
Find out more about this Airbnb here.
fancy sand and wood-colored decorated interior Airbnbs in Hawaii
Photo Courtesy of Hualalai Resort Villa Airbnb

Hualalai Resort Villa, Kailua-Kona, Big Island

When is a better time to splurge on an accommodation than on Airbnbs in Hawaii? This Hualalai Resort Villa is a great home to shell out some savings on. With a nearly $5,000-per-night price tag, it definitely isn’t for the faint of heart. This 6,300-foot accommodation includes an outdoor shower, receding walls and windows for unobstructed views, and five luxury bedrooms. And, of course, the devil is in the details, like the Egyptian cotton sheets, fire pits, and stone tubs. Plus, all guests of the Hualalai Resort Villa have full access to the Four Season Hualalai Resort.
This Airbnb sleeps up to twelve guests and costs $4,900 per night.
Find out more about this Airbnb here.
clean tiny house with large blue couch and yellow pillows
Photo Courtesy of The Little Farm House Airbnb

The Little Farm House, Captain Cook, Big Island

Over the past few years, tiny houses have become a trend. Most people have developed some inkling of curiosity about these smaller-than-life accommodations but don’t want to uproot their lives to try it. Staying in one for a couple of days while on vacation may be the perfect middle ground.
This tiny house located on the Kona side of the Big Island boasts epic sunsets and classy, yet minimalistic décor. And don’t worry, just because the house is small, that doesn’t mean that you’ll have to give up your necessities. There is a small kitchen, a bathroom, and even a 42-inch Smart TV within the walls of this little farm house.
This Airbnb sleeps up to three guests and costs $68 per night.
Find out more about this Airbnb here.
bright red yoga mats with ocean view Airbnbs in Hawaii
Photo Courtesy of Sustainable Oceanview Suite Airbnb

Sustainable Oceanview Suite, Papaikou, Big Island

Sustainability has become a major concern in the world today. Even while traveling, many aim to continue their sustainable lifestyles or even just try it out for a bit. This Sustainable Oceanview Suite just ten minutes outside of the city of Hilo allows guests to go just that. While there are quite a few sustainable Airbnbs in Hawaii, this particular sustainably-built accommodation fully embraces the lifestyle with kombucha happy hour, sunrise yoga sessions, and complimentary farm-sourced breakfast.
While the sustainability of this Hawaii Airbnb is the main highlight, we cannot forget about the location. Located within walking distance of the hidden gem of Onomea Bay and within driving distance of all of Hilo’s magical waterfalls, the location of this accommodation truly could not get any better.
If you’re someone interested in sustainability, check out our list of eco-friendly companies based in Hawaii that you should support!
Find out more about this Airbnb here.

The Coolest Airbnbs on Maui, Hawaii

living room with stone pillars and Hawaiian decor
Photo Courtesy of Jasmine at Ekena Airbnb

Jasmine at Ekena, Hana, Maui

Location, location, location! The number one thing on any visitor’s Maui bucket list is the road to Hana. While many try to go out and back in one day, others smartly decide to spend the night in Hana – and this Airbnb is perfect for that! Located in the quaint town of Hana, this home is truly a gem. With floor-to-ceiling windows, Hawaiian-style furniture, and breathtaking views, this Airbnb is a fantastic place to spend a night or even two.
This Airbnb sleeps up to five guests and starts at $340 per night (although this does depend on the number of guests as well as the season).
Find out more about this Airbnb here.
blue coral inspired bedding Airbnbs in Hawaii
Photo Courtesy of Paradise Awaits You Airbnb

Paradise Awaits You, Kihei, Maui

With 5-star ratings across the board, the Paradise Awaits You accommodation in Kihei has proven to be a hit with its previous guests. This impeccably decorated condo boats a fully stocked kitchen, soft bamboo sheets, and a private balcony. The best part of Paradise Awaits You is the fact that it is just steps away from one of the best beaches in Kihei!
This Airbnb sleeps up to four guests per night and costs $135 per night.
Find out more about this Airbnb here.

The Coolest Airbnbs on Kauai, Hawaii

colorful tiki shot glasses Airbnbs in Hawaii
Photo Courtesy of The Surf Shack

The Surf Shack, Princeville, Kauai

Sometimes the most treasured part of an Airbnb is not its unique form of accommodation or its location. Sometimes it’s the little touches that the fantastic host provides that put a smile on your face. This is the beauty of “The Surf Shack.”
Located within walking distance of Princeville Beach, superhost Kasey blessed The Surf Shack with every little gem she could think of. From a large collection of vintage tiki shot glasses to a stylish, curated newspaper filled with all of the best local shots, she sure has thought of everything. This Airbnb even has its own Instagram page to inspire even more potential guests to come visit. In other words, you better get to booking, because this sweet accommodation fills up fast!
This Airbnb sleeps up to five guests and costs $199 per night.
Find out more about this Airbnb here.
backyard with pool and golf course Airbnbs in Hawaii
Photo Courtesy of Kukuiula Club Villa Airbnb

Kukui’ula Club Villa, Koloa, Kauai

The Kukui’ula Club Villa is luxurious getaway away from the hustle and bustle of a city. Located on the sleepy, waterfall-filled island of Kauai, Kukui’ula is a fantastic place to unwind. On the property, you’ll have easy access to the Makai pool complex, a farm with produce picking and peacock bass fishing, golf courses, and tennis courts. Within just a few miles of the accommodation, there are beautiful beaches, amazing shopping, and wonderful restaurants.
This Airbnb sleeps up to eight guests and costs $2,039 per night.
Find out more about this Airbnb here.
So what are you waiting for? Have you booked your dream Airbnb in Hawaii? Or do you need a few tips on booking an Airbnb before you commit? If you love most of these Airbnbs and want to decide based on location, here is our guide to where to stay on Oahu.
Have you stayed in Airbnb in Hawaii that you think should’ve made it onto this list? Or have you stayed at one of the Airbnbs that are already on this list? Let me know in the comments!
Thinking about staying in one of these dreamy Airbnbs in Hawaii on your next trip to the islands? Pin this post for later!
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  1. Shoot, so many of these Air bnb links don’t work! The Oahu ones are the ones I was looking at. Are they no longer around?

    1. Yeah once the Airbnbs are no longer listed on the site, the links stop working! And since this article is a couple of years old, many of the links no longer work. Thanks for bringing this to my attention, Katrina! I’ll update this article when I get the chance :).

      Sarah from Borders & Bucket Lists

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