Remedy That Travel Itch with 22 of the Coolest Airbnbs Across Hawaii

coolest hawaii airbnbs in maui, the big island, oahu and kauaiVaccinations are making their way around the US, and there’s a calming cloud of hope overhead. Perhaps you’re starting to seriously consider that dream vacation. Hey, we don’t blame you. Hawaii is always on the top of our minds! Something so magical flowing through those isles. Maybe it’s premature, but the coolest Airbnbs in Hawaii research is in full swing. Don’t judge our travel itch!

If you’re planning a (much needed) Hawaiian getaway, you might already know which island that you want to explore. Or perhaps it’s an island-hopping kind of trip? Either way, we encourage you to delve into all the wonders, gorgeous vistas, and bountiful tropical forests that these islands have to offer.

From tree houses to mango farms and (of course) oceanfront properties, we rounded up the coolest Airbnbs to stay in across the majestic isles of Hawaii. We’ll organize our excitement by island:

Coolest Airbnb Rentals on the Big Island

1. Big Island Bamboo Treehouse

starting at $240/night

Quiet, secluded, unique, and cozy bamboo treehouse on the Big Island is just minutes from Volcanoes National Park. Beautiful features, inside and out. Test out treehouse living and bamboo beauty, but with loads of extras. This is the only true bamboo tree house on the islands – few places could compare for both structural beauty and lanai views.

2. Tropical Garden Retreat on an Organic Mango Farm

starting at $131/night

Soak up the sun and unwind in the abundant outdoor living space which blends seamlessly with the interior of this stunning ground-level retreat. The home is constructed with architectural cedar poles and the living space is open air, allowing you to enjoy the natural world around you. Both the bedroom and kitchen are enclosed. The space is decorated in an exotic, Modern-meets-Indonesian style!

3. Romantic Oceanfront Bali House with Hot Tub at Kehena Beach

starting at $209/night

Wake up to amazing sunrises in this ocean front home imported from Bali and re-constructed in Hawaii. Only 150 ft away from the black sand beach, home to spinner dolphins and humpback whales during the winter. This home contains authentic artwork and furnishing’s imported from Bali and is located near the Volcano, waterfalls, shopping and restaurants.

4. Magical Bohemian Retreat Near Kealakekua Bay

starting at $181/night

Nature Lovers! Wake up eye-level with the canopy in a lofted bedroom with floor-to-ceiling windows and bohemian furnishings. Nestled among mango trees and rich with daylight, this tropical hideaway offers an unmatched open-air environment with eclectic adornment.

5. Puna Rainforest Retreat Hot Spring Rainbow Cottage

starting at $122/night

The Rainbow Cottage overlooks the 20 acre estate surrounded by rainforest within the Puna Forest Reserve, 4 miles from Pahoa. Enjoy active steam vents with pure water steam, warm ground and experimental hot tubs over steam vents. With no visible neighbors the property is secluded and peaceful with citrus, bananas, fruit orchard, avocados, palms, and many flowers.

6. Aolani House Resort Style Home with Infinity Pool

starting at $1,789/night

Recently ranked #1 in Conde Nast Traveler: “The Best Airbnbs in Hawaii”, this resort style home will have you relaxing the moment you step through its doors to expansive 180 degree ocean views. Built by the same builders as the Four Seasons on the Big Islandt, this spot is nestled right behind 5 acres of Kona Coffee + MacNut farms for ultimate privacy. The private + heated salt water infinity pool and spa are the ideal place to watch sunset.

7. Aloha Nature Lovers

starting at $80/night

Aloha Nature Lovers! Located between Waipio Valley + Volcano National Park, this spot is convenient and very private. One can spend days chasing the many private waterfalls and exploring this property. Enjoy each breath of pure sweet air. The little cabin has a great ocean view to watch the ships go sailing by + clouds parade down the coast. Nights are wonderful just sitting around the campfire, star gazing + telling stories.

8. Amazing Family (Tiny) Home on Volcanic Lava Field

starting at $185/night

Wake up amazed! Enjoy otherworldly vistas of volcanic scenery from this unique, off-grid tiny home at the foot of the world’s most active volcano. Two individual pods are bridged by a lanai in the middle, creating a breezy area for sitting, dining, and planning family adventures that they will never forget.

9. Kūono at Volcano

starting at $350/night

Set out on an adventure and return to a retreat of peace and relaxation just five minutes from Volcano National Park. Open the red front door to Kūono at Volcano to find 14 foot floor to ceiling windows connecting you to the outdoors. Nestled in a forest of beautiful Ohia trees, you will be immersed in natural beauty both inside and outside.

10. Dreamy Tropical Tree House

starting at $300/night

Clearly one of the coolest Airbnbs in Hawaii: Red cinder leads you through the dense jungle to your secluded bamboo treehouse! Nestled on top of stilts 15′ up in the canopy of the local flora, ascend to your retreat via the trapdoor or begin your adventure in Volcano National Park 10 miles away.

Best Airbnb Rentals in Oahu

11. North Shore Surf House

starting at $500/night

Wake up to the waves in this oceanfront beach house. Sweeping views from North Shore’s famed pipeline all the way to Sunset Beach from your private yard. Ocean view master bedroom is equipped with a walk in closet, personal surfboard rack and attached bathroom with double sinks.

12. Welcome to Maluhia – Ocean Front Serenity Home

starting at $285/night

Welcome to beautiful Kaneohe bay front home. The house is right ON the ocean bay where you can see sea turtles and other marine life on a daily basis. Included is a two person kayak so you can paddle to the nearby sand bar. Serenity now!

13. Ground Floor Villa on Ko Olina Beach

starting at $603/night

This unique and highly coveted ground floor 2 bedroom, 2 bath oceanfront resort condo has ocean, sunset and mountain views. Walk out to the beach, pool and beach bar areas in moments from the Hale Kuapapa (House of Tranquility) Ko Olina Beach Villa!

14. Waimea Bay North Shore Ocean Front

starting at $529/night

This beautiful home at Waimea Point, centrally located in the heart of the North Shore, is walking distance to world class white sand beaches. The spectacular view that overlooks the Pacific ocean and Waimea Bay makes this house a truly unforgettable spot to spend your Hawaiian dream vacation.

Maui Airbnb Rentals

15. Your Own Private Resort with Breathtaking Ocean Views

starting at $1,050/night

This home boasts open living spaces that reflect the spectacular views surrounding it! Sink into the hot tub, curl up by the outdoor fire pit, or relax with a good movie in front of the 75″ TV. Step into the master bedroom’s luxurious slate shower or expansive Cleopatra tub and wash your cares away. Yes!

With Covid-19 restrictions moving towards lifted, maybe you’re thinking about saying ‘I do’ on one of these magical islands?! This mindful wedding in Maui blends Hawaiian culture and sustainability. So much wedding inspo!

16. North Shore Lookout Maui

starting at $411/night

North Shore Lookout Maui is a boutique bed and breakfast situated on nine acres of land in Upcountry, Maui. With ocean views of the North Shore coast line and West Maui mountains, its tranquil setting is ideal for those seeking a unique experience. One of the coolest Airbnb rentals in Hawaii especially because of that pool! Wow.

17. Adorable Garden Gingerbread House

starting at $195/night

Romantic hideaway alert! This property has the lush beauty and privacy of Hana, without the drive! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops…on a private gated property with an organic nursery.

18. Bamboo Temple with Dreamy Views

starting at $376/night

Possibly the coolest Airbnbs in Hawaii just because of the view! Experience that offers comfort and privacy with a sunrise view every morning, ocean views all day, and stars all night. The Bamboo Temple is a romantic and breathtaking refuge of what dreams are made of.

Best Airbnb Rentals in Kauai

19. Stunning Hanalei Bay + Ocean View with Private Pool

starting at $750/night

Discover Hanalei Bluff House located in Princeville overlooking beautiful Hanalei Bay. This newly remodeled stunning open concept house with private secluded pool offers the best of modern tropical living. Hanalei Bay, ocean, river, mountain, waterfall, lush valley and prime sunset views can be enjoyed throughout the home and from multiple lanais!

20. The Nene Nest

starting at $235/night

The Nene Nest, Kauai is a classic, sugar plantation- style cottage located on the always sunny West Side of Kauai. Just 152 steps from the ocean, it offers a true Hawaii feel. Designed with a ‘slow’ pace in mind, the hope is that you enjoy every part of your stay; sipping coffee on the updated lanai in the mornings with a book in hand, or by relaxing on the beach surrounded by sunshine + ocean breezes on the beautiful garden isle.

21. Nico Hale

starting at $261/night

Secluded jungle cottage on the North Shore of Kauai. The house is a short drive from local beaches and hikes on the north shore of Kauai in the neighborhood of Wainiha. The home is surrounded by lush tropical jungle and fruit trees, which is why it’s one of the coolest Airbnbs in Hawaii!

22. The Surfshack with Breathtaking Ocean Views

starting at $279/night

The most incredible location with Panoramic ocean views! Nestled on an overlook with amazing ocean views, stunning sunsets, and the famous Bali Hai, you’ll never want to leave this beautifully boho styled 2 bedroom, 2 bath condo. It’s everything you’ll need and want for the most relaxing stay of your island vacation. Only steps away from food, drinks, the pool and the beach. Whale watch from the lana’i in the winter, or snorkel through beautiful hideaways beach in the summer.

If you are thinking about Hawaii and not sure which island, you can find our Oahu Travel Guide hereLanai Travel Guide hereMaui for the Adventurous Couple hereAndaz Resort on Maui heree and the Big Island here.

Jen + Jason ventured to magical Kauai back in 2019, and journaled all about it!

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All photos belong to their respective Airbnb owners and are sourced via Airbnb.