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8 Dreamy Airbnbs in Hawaii for an Unforgettable Vacation

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Sometimes a getaway isn’t just about the location and the things to do there. Sometimes, the accommodation that you choose to stay at is a big part of the unique vacation experience — and this is the case for quite a few Airbnbs in Hawaii.

You can stay in treehouses, at Hawaiian-style homes, or even in the same luxurious beach house that President Obama stayed in!

Hawaii is a dreamy vacation spot regardless of when you go. One of the best ways to ensure that you have a perfect vacation is by picking a place to stay where you’ll feel relaxed and at home. 

So if you’re looking for the best Airbnbs in Hawaii for you to stay at, this list has got you covered! You’re guaranteed to find the perfect Airbnb for you.


8 of the Best Airbnbs in Hawaii for You to Stay At

Hawaii consists of several islands and it can be tough to choose which island you want to vacation on. To help you narrow down the choices, I’ve chosen eight of the very best Airbnbs in Hawaii. Keep in mind that this list doesn’t include every single Airbnb in Hawaii. 

If you’re interested in looking at more Airbnbs in Hawaii, here is a map highlighting more accommodation options. 

1. Dreamy Tropical Treehouse on the Big Island of Hawaii

There are so many pretty Airbnbs in Hawaii.

Dreamy Tropical Tree House | Photo Credit: Airbnb

Just about every little kid wishes that they could move into a treehouse. This dreamy, tropical treehouse on the Big Island of Hawaii can make that dream happen, even if it’s just for a few days.

But, this treehouse doesn’t include swings and slides that would be perfect for five-year-olds. It has elements that adults can appreciate as well. Instead of a swing, this treehouse includes a hanging bed with sheer sheets swaying below the structure.

Rather than a slide, you’ll find a wrap-around balcony that gives you unobstructed views of the bright green Hawaiian jungle around you.

And, I certainly can’t forget to mention all of the fun amenities, including a gramophone, a deck of cards, and tiki torch flashlights.

If all of these perks aren’t enough to convince you to stay at this awesome treehouse, the location might be just the things you need to take it over the top. If you’re looking for an off-the-grid getaway for some peace and quiet, this home is absolutely perfect!

At the same time, it’s just 20 minutes from the famous Hawaii Volcanoes National Park, where you can check out a handful of volcano craters, warm up by the steam vents, and maybe even catch some lava flowing!

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2. Luxurious Beach House that Hosted President Obama in Kailua, Oahu

This is one of many Airbnbs in Hawaii.

Plantation at Paradise Point | Photo credit: Airbnb

Every winter during his presidency, President Barack Obama and his family vacationed in the small town of Kailua on Oahu, Hawaii. During each visit, they stayed at the same luxurious beach house — and you can stay here too!

While the inside of the home boasts large windows, spacious rooms, and olive accent walls, it’s the backyard that’s the main highlight. You can swim in the lagoon-like pool, grill up a bite to eat, and take a nap in the quiet cabana.

With all of these wonderful features, this beach house is definitely worthy of a president staying here. This vacation home also boasts a fantastic location. Situated in the most secluded part of Kailua Beach, you can enjoy your day in the beautiful turquoise ocean completely undisturbed.

You’ll also be very close to Lanikai Beach, the Lanikai Pillbox Hike, and the Kailua Farmers’ Market.

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3. Inviting Surf Loft on Maui

If you're looking for the best Airbnbs in Hawaii, read this post.

Surf Loft | Photo Credit: Airbnb

This inviting surf loft on Maui is so well decorated that it deserves a feature on an HGTV show. With an adorable blush pink couch, a surf-inspired gallery wall, and a patio with a hanging pod chair and twinkle lights, you’ll never want to leave! It’s definitely one of the best Airbnbs in Hawaii.

There are all the thoughtful features that give this surf loft an edge. You can wake up each morning with a mug of Hawaiian coffee, do a little yoga using the provided mats, learn to play your favorite songs on the ukulele, and listen to some amazing tracks on a vinyl record player.

You’ll also have access to a common area, complete with a lovely pool, a relaxing hot tub, and a handful of barbecues.

This surf loft is located in the lovely town of Kihei. While there, you can savor the delicious sweet treats from Ululani’s Hawaiian Shave Ice, soak up the sun at the hidden Cove Beach Park, or take a Molokini snorkeling tour.

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4. Kukui‘ula Club Villa on Kauai

Kukui'ula Club Villa is one of the best Airbnbs in Hawaii.

Kukui’ula Club Villa | Photo Credit: Airbnb

Kukui‘ula is one of the most lavish places to stay in Hawaii. The whole community is filled with grand vacation rentals, including this gorgeous Kukui‘ula Club Villa.

This villa blends indoor and outdoor living together. First, the kitchen, living room, and dining room all completely open up to the backyard – and its stunning ocean views. Second, the house also includes many natural materials, including dark wood and lava rock.

There’s a good chance that you’ll spend most of your time at this villa in the backyard. You can suntan on the sun loungers, swim in the blue private pool, wash off in the lava rock outdoor shower, and roast marshmallows over the firepit.

You’ll also have access to a common area on the Kukui‘ula property, which includes a pool, tennis courts, a golf course, and even a farm with fresh fish and produce!

This Kukui‘ula Club Villa is located in Koloa, a part of Kauai that is just as posh as the villa itself. While there, you can wander around the luxurious The Shops at Kukui‘ula, dine at the award-winning Eating House 1849, or practice your skills at the Kukui‘ula Golf Course. 

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5. Retro Island-Inspired Condo in Waikiki, Oahu

There are so many beautiful Airbnbs in Hawaii.

Islander’s Ocean View | Photo Credit: Airbnb

This retro condominium could’ve been pulled off a tropical 1950s TV show set. With an array of Hawaii vintage posters, a pretty pink couch, and an antique teal refrigerator, this vacation home is spunky and daring.

This fun condo includes everything you need and more. You can hang out on the succulent-spotted balcony, drink a fruity beverage out of one of the pineapple tumblers, and slather on some provided SPF 30 sunscreen before heading out for the day.

And to add to the appeal, this condo is located in the heart of Waikiki! It’s just a couple of blocks from both the shopping of Kalakaua Avenue and the sunny shores of Waikiki Beach.

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6. Tiny House on Volcanic Lava Field on the Big Island of Hawaii

This is one of the most unique Airbnbs in Hawaii.

Amazing Family Tiny Home | Photo Credit: Airbnb

One of the coolest Airbnbs in Hawaii is a one-of-a-kind tiny house on a volcanic lava field. This awesome little home was built by a tiny treehouse design company called ArtisTree, which has created amazing homes everywhere from Sonoma, California to Zihuatanejo, Mexico. 

Since this house is one of a kind, its design is certainly distinctive. The home is actually split into two halves with a shaded outdoor deck in the middle. I’ve never come across a home quite like it before.

While staying at this earthy-colored house, you can wake up to views of the jagged lava rock, enjoy your morning caffeine out on the deck, and play a few card games in the cozy living area.

And the location on a volcanic lava field is certainly special as well. From this tiny house, you can actually see the famous orange glow of the lava rocks at night.

You’ll also be close to many beautiful natural features, including the gravity-defying Holei Sea Arch and the sparkling Pohoiki Black Sand Beach.

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7. Hale Kamapua‘a: Hawaiian-Style Oceanfront Villa on Kauai

Hale Kamapua'a is one of the prettiest Airbnbs in Hawaii.

Hale Kamapua’a | Photo Credit: Airbnb

If you’re hoping to experience a traditional Hawaiian-style home, Hale Kamapua‘a on Kauai is definitely a great option. With its comfortable wicker furniture, ubiquitous nature patterns, and warm wood features, Hale Kamapua‘a is a great example of most houses in the islands.

While staying at this lovely home, you can embrace the slow island-style pace of life. Wake up late, enjoy a cup of coffee out on the balcony, and maybe even whip up a batch of banana pancakes. And once you’re rested, caffeinated, and full, you can explore the beautiful nearby area.

Hale Kamapua‘a is located in the little town of Hanalei, Kauai. But despite its small size, Hanalei has so many things to do. You can start hiking the Kalalau Trail, peek at the view of the taro fields from the Hanalei Valley Lookout, and soak up the sun at Hanalei Bay.

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8. Aolani House on the Big Island of Hawaii

This is one of the prettiest Airbnbs in Hawaii.

Aolani House | Photo Credit: Airbnb

Thanks to its feature in Airbnb Magazine, the Aolani House is certainly one of the best Airbnbs in Hawaii. With a tiki-torch lined walkway, unparalleled ocean views, and a lengthy infinity pool, the Aolani House is the perfect island getaway. 

As you explore the inside of the Aolani House, you’ll constantly find things that’ll set this vacation home apart – from the luxury WOLF appliances in the kitchen to the Sonos sound system in the living room. But the backyard, with its ocean view pool and bubbling hot tub, is the real highlight of the home.

The Aolani House is located in Kailua-Kona, the most visited city on the Big Island of Hawaii. While there, you can enjoy the breathtaking Kua Bay, say hello to the seahorses at the Ocean Rider Seahorse Farm, brush up on your Hawaiian history knowledge at the Kamakahonu National Historic Landmark, and snorkel with manta rays at night.

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Do you have any vacation rentals to add to this list of the coolest Airbnbs in Hawaii? Let me know in the comments below!


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