Updated: June 2022
This post has been updated to include a roundup of my favorite boutique properties and vacation rentals in Hawaii.
Planning your dream trip to the Hawaiian islands? Some folks have a favorite place and love to stick Maui, Oahu, Kauai, or the Big Island…while others like to sample them all and go island hopping.
Perhaps you’re not sure which of the Hawaiian Islands you should travel to? No worries! If you have the time, I would highly encourage checking them all out to explore all the wonders, gorgeous vistas, and bountiful tropical forests.
One major thing to keep in mind while adventuring around Hawaii is to make sure to wear reef-safe sunscreen to do your part in helping preserve the natural beauty of both the land and sea.
And you might want to sample these 10 local foods while you’re in Hawaii, too!
From tree houses to farm stays to incredible oceanfront properties, I rounded up the coolest Airbnbs to stay in across Hawaii. A number of these are from the Big Island (they do call it the Big Island for a reason), but there are a handful of places throughout Maui, Kauai, and Oahu, too!
Here are the coolest and most unique Airbnbs to stay at in Hawaii!
North Shore Surf House
Haleiwa, Oahu
Location, location, location! If you want to wake up to the waves, this oceanfront beach house is the place! With sweeping views of the Pipeline, all the way to Sunset Beach’s West Peak, this place is a true gem!
BOOK HERE
The Surfjack Hotel & Swim Club
Honolulu, Hawaii
The Surfjack Hotel & Swim Club in Waikiki has vintage-inspired bungalows and suites. I love all the hand-crafted furniture, custom-tile bathrooms, and eclectic artwork that decks out the place.
BOOK HERE
The Laylow, Autograph Collection
Honolulu, Hawaii
Just five minutes away from Waikiki Beach, The Laylow is a mid-century modern hotel that’s minimal, retro, and oh-so-cool.
BOOK HERE
Tiny Home on Volcanic Lava Field
Pahoa, Big Island
If you’re looking for a seriously unique Hawaii experience, you can see Pele’s Orange glow from this Airbnb! This otherworldly setting provides a cool and off-grid stay at the foot of the world’s most active volcano.
BOOK HERE
Tropical Garden Retreat on a Mango Farm
Captain Cook, Big Island
Modern meets Indonesian style on this organic mango farm! Soak up the sun and embrace the abundant outdoor living space. This place is airy and peaceful and ideal for connecting with nature.
BOOK HERE
Magical Bohemian Retreat
Captain Cook, Big Island
Located near Kealakekua Bay, this place is the space for nature lovers! Wake up to the canopy in a lofted bed and embrace the sun via the gorgeous floor-to-ceiling walls. Sequestered away in a grove of mango trees, this place is an eclectic and tropical delight!
BOOK HERE
Bamboo Bungalow
Keeau, Big Island
This slice of paradise sits on 1-acre of a tropical orchard with so many fruit trees, orchids, herbs, and bamboo. There’s an indoor bath and shower along with an outdoor bamboo shower (and it doesn’t get better than that, does it?).
The cozy space is so thoughtfully stocked and the ideal place for a foodie who loves local flavors!
BOOK HERE
Dreamy Tropical Treehouse
Fern Forest, Big Island
Fancy staying in a secluded bamboo treehouse? Hidden away under a canopy of local flora, you’ll ascend to your oasis via a trapdoor (so cool!).
This Dreamy Tropical Treehouse is just 10 miles away from Volcano National Park, making it the ideal place to relax and unwind after a day of adventuring.
There’s a hanging bed at ground level (talk about dreamy!), and an overall sort of vintage 1970s vibe throughout the property. I’d definitely want to sample the local coffee and snacks provided while hanging out on the wrap-around lanai, which has 360-degree views of the lush jungle!
BOOK HERE
The Rainbow Cottage
Pahoa, Big Island
Fancy a stay at this charming Rainbow Cottage? Enjoy the pool, volcanic hot spring tubs, and rainforest trail on this forest reserve. The 20-acre property is home to citrus, bananas, avocados, palms, and many more flowering plants.
BOOK HERE
Tropical Tree House in the Rain Forest
Volcano, Big Island
Perfect for two, this tropical home offers off-grid living with cozy homey comforts Soak in the hot tub while you listen to the sounds of the forest and then enjoy a warm outdoor rain shower!
BOOK HERE
Private Cottage Farm Stay
Hawaii County, Big Island
This private cottage is a lovely retreat with its lanai where you get sweeping ocean views. The deck is ideal for yoga and meditation, and whale watching—if it’s the right season!
Guests are welcome to pick fruits and eggs and explore the farm and adventure to local waterfalls and swimming holes on the property. Located on 10 gorgeous green acres on the Hamakua Coast, this quaint space is an ideal retreat.
BOOK HERE
Kealakekua Bay Bali Cottage
Captain Cook, Big Island
When you think of the ultimate Hawaiian holiday, you’ll probably imagine a quiet and peaceful village where all you can hear are waves crashing and the calls of local birds. Well, this Bali Cottage in Kealakekua Bay on the Big Island of Hawaii will provide just that!
Crafted from antique Balinese panels, it’s almost like you’ll get to experience two unique places in one!
The tropical yard is complete with a charming gazebo and barbecue…and tons of local birds! No need to drive to the beach—you can walk in just under two minutes to a beautiful beach park!
Glass House
Volcano, Big Island
For a truly unique experience, stay at this Glass House in the heart of the Big Island. Connect with nature by immersing yourself in the tropical rain forest and listen to the rain pitter-patter on the glass ceiling.
BOOK HERE
Luxury Cottage with a Saltwater Spa
Kihei, Maui
This cozy space is perfect for a couple’s getaway! Slip into the saltwater tub on the private deck and enjoy a cocktail. There’s an outdoor shower to rinse off after a day at the beach, too.
There’s tons of beach equipment for a fun day in the surf and sand, from boogie boards to sunscreen to snorkel gear and umbrellas, as well.
BOOK HERE
Designer Industrial Studio Steps from the Beach
Kihei, Maui
Coastal meets industrial in this designer studio. Just steps from the beach at Kihei Bay Surf, this modern space is designed for two.
BOOK HERE
Duke’s Cottage Bed & Breakfast
Makawao, Maui
Located in Makawao on Maui this North Shore cottage is the perfect place to find your aloha! This boutique bed and breakfast has a vintage Hawaiian theme with a modern twist.
BOOK HERE
Modern Meets Luxurious Beach House
Lahaina, Maui
If you love modern style but want to be on the coast, this breezy cottage is the perfect blend of the two! With soft whites and pastel blues this luxurious spot is tranquil and cool. Experience life like a local on Maui as it’s just down the road from Lahaina.
BOOK HERE
Ocean View Home with Private Pool
Princeville, Kauai
Located in Princeville, the Hanalei Bluff House is a newly remodeled open concept house with a gorgeous private pool. The house is ideal for families or groups of up to six.
BOOK HERE
Koa Kea Hotel & Resort
Koloa, Kauai
This boutique resort is located on Poipu Beach on Kauai’s south shore. From the upscale furnishings to the gorgeous balconies to the outdoor pool — what’s not to love?
BOOK HERE
Wow!
Great work!
It’s hard to choose one of these places.
All beautiful!
So many cool places, right?
Hi Kiersten. Every time I visit your blog, I am mesmerized by the images that you post. Sometimes I really visit just for the pictures.
Great list of places. It makes planning to visit so much easier. I was especially impressed by the “Private Cottage Farm Stay”. That looks so cozy. 🙂
Hey Pooja! Thanks for the kind words 🙂 And doesn’t it look so lovely??