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The Coolest Airbnbs in Hawaii
Hawaii is a true paradise! So I’ve rounded up the coolest Airbnbs in Hawaii on the islands of Maui, Kauai, Oahu, and the Big Island.
The Ultimate Hawaii Travel Guide
Pro Tip: Hawaii is a year-round destination. The closest thing Hawaii has to an off-season is February. You’ll have some of the lowest prices and crowd numbers this month because it’s after the holidays and before spring breaks.
Hawaii is also one of the Best Destinations To Visit In February because it’s the peak season for humpback whale-watching, so you’ll have lots of opportunities to see these impressive gals.
Here are the coolest Airbnbs in Hawaii for your dream trip!
Romantic Cottage
Hanalei, Kauai
2 guests1 bedroom2 beds1 bath
This cottage is perched on a bluff overlooking the Wainiha River on an acre of lush gardens. You’ll have stunning views of the entire river valley. The private pool, hot tub, and patios take this property over-the-top, and the home is just two miles from some of the most beautiful beaches in the world.
Surf House
Haleiwa, Oahu
3 guests1 bedroom1 bed1.5 baths
If you want to walk out your door onto the beach and fall asleep listening to the waves, then this oceanfront house is for you. From your private yard, you’ll have stunning views from North Shore’s famed Pipeline all the way to Sunset Beach’s West Peak.
Luxury Villa
Kailua, Oahu
12 guests6 bedrooms7 beds8 baths
Presidents and celebrities have stayed in this mansion! The property has a Japanese-style garden and a lagoon pool with waterfalls, lava rocks, and beautiful rainforest foliage. You’ll also have a jacuzzi, BBQ, gourmet kitchen, two living rooms, and multiple indoor and outdoor dining spaces.
The Dream Temple
Haiku, Maui
6 guests bedrooms beds1 bath
Immerse yourself in the natural beauty of Maui at this eco-designed bamboo cottage. There are three covered decks, a grill, a hot tub, and a resort-style pool. Plus, the home’s lush, tropical landscaping makes this a true jungle paradise.
Duke’s Cottage B&B
Makawao, Maui
2 guests1 bedroom1 bed1 private bath
This boutique bed and breakfast has a vintage Hawaiian theme with a modern twist. Your private room has a bathroom, kitchenette, and a patio. You’ll be able to enjoy the property’s pool, jacuzzi, fire pit, hammock, and outdoor seating areas, and the breakfast here is the perfect way to start your day.
Discover all of the Dreamiest Vacation Homes in Maui
Tropical Paradise
Captain Cook, Big Island
5 guests bedrooms beds baths
This modern-meets-Hawaiian-style home is perfectly located for exploring the island. There are incredible views of the ocean, vaulted ceilings, and a covered lanai. You’ll also love the six-person hot tub.
Rainforest Retreat
Rainforest Retreat
Volcano, Big Island
6 guests2 bedrooms3 beds baths
This home is in the rainforest on the slopes of the Kilauea volcano, right outside Hawaii Volcanoes National Park. You’ll be at an elevation of 3,750 feet, so you’ll want layers for the evenings and mornings. The house comes with large bedrooms, a luxurious covered porch, and a hot tub.
Tiny House on a Lava Field
Kalapana, Big Island
5 guests bedrooms beds1 bath
If you’re looking for a truly unique and off-the-grid property, then this vacation home is for you. You’ll be at the foot of one of the world’s most active volcanos, and you can see Pele’s Orange glow from this property!
Recommended Tours in Hawaii
Shop My Hawaii Essentials
What do you think are the coolest Airbnbs in Hawaii? Share with us in the comments!
Plan The Rest Of Your Trip
Frequently Asked Questions
How do I travel between Hawaiian Islands?
The best way to island-hop in Hawaii is to fly. Hawaiian Airlines usually has the cheapest rates and the most flights. You could all take an inter-island cruise, but please ensure you only use sustainable cruise companies.
What is the best time of year to go to Hawaii?
Hawaii is made up of micro-climates, so the weather varies significantly from island to island and from one side of an island to the other. The year-round warm weather (rarely going below the mid-70s or above the mid-80s) means Hawaii is a great destination any time of the year. So Hawaii doesn’t have an off-season.
April – September is the most popular time to visit Hawaii because these are the warmest and driest months. The ocean is calmer, giving you access to more water activities with better sailing conditions. Be prepared to pay the highest prices during these months. The islands will also be crowded, so book accommodation, tours, and rental cars in advance.
The weather in Hawaii is marginally cooler from October – March, and these are the wettest months of the year. Pro Tip: the islands’ west coasts are significantly drier than their east coasts.
October – March is whale-watching season, and the crowds and prices will be lower (though not significantly). These months have some of the largest swells of the year, so surfers will swarm the beaches.
What are the best places to visit in Hawaii?
Oahu: Waikiki Beach, the North Shore, Diamond Head, Kualoa Ranch, Ho’omaluhia Botanical Garden, Pearl Harbor.
Kauai: Wailua Falls, Maha’ulepu Heritage Trail, the Nā Pali Coast, Wailua River, Waimea Canyon.
Maui: Hana, Wai’anapanapa State Park, Haleakala National Park.
Hawai’i (Big Island): Hapuna Beach, Hawaii Volcanoes National Park, Akaka Falls, Rainbow Falls, Waipi’o Valley.
What should I bring to Hawaii?
Hawaii’s climate and culture mean the dress code is very casual. Many visitors to the islands never change out of their swimsuits and sandals. You’ll want a sarong or cover-up for your swimsuit when shopping, dining, or riding in a taxi. And men should always wear a shirt inside.
Bring fast-drying clothes and shoes. If you’re doing any hiking, bring moisture-wicking and UV-protected clothes. For boat tours, bring a hat with a neck strap to keep it from blowing away, and have a strap for your sunglasses.
You’ll also want a lightweight rain jacket. If you’re going to visit Hawaii’s national parks or one of the higher-altitude volcanoes, you’ll want long pants and a jacket.
In addition to your usual travel essentials, you’ll want these items:
Bags for your wet and sandy shoes and clothes. If you’re visiting one of the public beaches, there usually aren’t showers for rinsing off. So always have a bag handy for wet and sandy clothes.
Electrical outlets in Hawaii are Types A and B. So if you’re from the U.S., you won’t need an outlet adaptor. But British, European, and other travelers will need an adaptor.
Sun protection. The sunshine is gorgeous but brutal in Hawaii, and you’ll usually find that there’s minimal shade on the beaches. So bring sunglasses, sunscreen for your skin and lips, a hat, and UV-protected shirts.
What are the best national and state parks to visit in Hawaii?
1. Diamond Head State Monument, Oahu
2. Haleakala National Park, Maui
3. Hawaii Volcanoes National Park, Hawai’i (Big Island)
4. Heʻeia State Park, Oahu
5. ʻĪao Valley State Park, Maui
6. Nā Pali Coast State Wilderness Park, Kauai
7. Waianapanapa State Park, Maui
8. Waimea Canyon State Park, Kauai
What are the best scenic drives in Hawaii?
1. Chain of Craters Road, Hawai’i (Big Island)
2. Garden of the Gods, Lanai
3. Hamakua Coast, Hawai’i (Big Island)
4. Kamehameha Highway, Oahu
5. Road to Hana, Maui
6. Route 560, North Shore of Kauai
7. Summit road to Mount Haleakala, Maui
8. Waimea Canyon Drive, Kauai
How many days do you need to visit Hawaii?
Give yourself at least 3-4 days to explore each Hawaiian island.
Do I need to rent a car in Hawaii?
If you’re staying in a vacation home on any of the islands, then you’ll want to rent a car.
If you’re staying in a resort and planning on leaving your hotel, then a car is essential on all of the Hawaiian islands. You can hire a driver, and taxis and rideshares are common, but these are expensive. So if you’re going to leave your resort more than a couple of times during your trip, you’ll probably save money by renting a car.
Plus, renting a car gives you flexibility and the freedom to set your own itinerary.
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This article about the coolest Airbnbs in Hawaii is not a sponsored post, and the thoughts and opinions expressed in this post are entirely my own. Some of the links in this post about the coolest Airbnbs in Hawaii are affiliate links, and, at no cost to you, I may earn a small commission from this post about the coolest Airbnbs in Hawaii.
