Choosing the coolest vacation rentals in Hawaii can be challenging, as the collection of accommodation options here are simply dreamy. Honestly, hundreds of Airbnbs could have made the cut. From treehouses blended with the jungle to swanky apartments in developed areas, we have narrowed it down to these gorgeous options. Your experience in Hawaii can be tailored to your travel needs and wants, and it will be everything you imagined it to be.
Peaceful Rainforest Treehouse Retreat - Volcano
Treehouses are the most magical structures to stay in when visiting Hawaii—and this one is no exception. A colorful path lined with tropical foliage winds to the multilevel haven. Also close to Hawaii Volcanoes National Park, there’s much terrain to be hiked and explored. This is an optimal place for experiencing the natural environment, as you’re surrounded by guava and eucalyptus trees, while critters such as geckos and chameleons scoot around the grounds.
Hawaii Life Oceanfront Cottage - Kilauea, Kauai
This one-bedroom retreat on the Garden Isle sits right above Secrets Beach on a private knoll providing panoramic mountain and ocean views. It boasts 34 private oceanfront acres on Kauai’s most exclusive road, popular among A-list celebrities. It has a fabulous lanai where you can relax while gazing out at ocean and sunset views, and from your bedroom with its floor-to-ceiling glass doors, you’ll be able to wake up with that stunning view too. It also has a gourmet kitchen, while the dining and sitting areas boast even more enchanting views of the private garden and the sea.
Oceanfront in Paia with Pool and Hot Tub - Maui
Located just steps from the sandy beaches of Paia on the north shore of Maui, including the long stretch of pristine white sands at Baldwin Beach, this oceanfront home accommodates up to six guests in four bedrooms. Nearly every room in the house provides an ocean view and you’ll also have a hot tub and 50-foot lap pool where you can swim or soak with a view of the Pacific. It enjoys a secluded feel, lined with vegetation and fenced in while providing all the essentials and more, like a well-equipped kitchen, an extra-spacious living room, BBQ grill and a washer/dryer.
Modern Elegance Near Pohoiki and Kehena Beaches - Pahoa
This sleek private screen home accommodates up to four guests in two bedrooms, both of which are master suites, and has been featured in Dwell magazine. It includes a 500-foot deck furnished for dining and relaxing under the monkeypod trees and sits just three-quarters of a mile north of the black sands of Kehena Beach where dolphins are known to come by and frolic with swimmers. It includes private outdoor showers, a well-stocked kitchen and free Wi-Fi. There’s no TV, but who needs that when you have all this?
Adorable Garden Gingerbread House - Makawao
Described as a “gingerbread house”, the cozy continues within the cabin-like interior. Believe it or not, Jimi Hendrix actually stayed in this house back in the day when on tour in Maui, but the inside has recently been remodeled since it has been around since the 1930s. The hosts can accommodate everything from relationship coaching to massage sessions, and also have some great tips on where to scuba dive. You can also pick your own fruit from designated trees. This little cottage is a serene escape from it all.
Pinnacle Escape from Reality in Upcountry - Maui
Offering an enviable Maui hilltop location, Pinnacle is truly a dream. You’ll enjoy a 180-degree unobstructed view that includes the ocean to the north, part of Molokai, the full west Maui mountains, Maui’s central valley, and a slice of the Pacific to the south. In addition to the beautiful pool, you’ll have 3,100-square-feet of interior space with ocean views throughout. It’s all air-conditioned with central A/C and includes a gourmet kitchen, flat-screen TV with TIVO and a DVD player, plus smaller TVs in the kitchen and master bath.
The Lotus Garden - Hilo
Formerly a root vegetable processing factory, this lush apartment has taken quite the upscale vibe. Light color pallets and dreamy accents create a heavenly atmosphere, and the naturally lit outdoor shower is just the cherry on top. Since it’s located in the developed part of Hilo, with wonderful cafes and coffee shops blocks away, this is a fitting experience for those not fond of the inconveniences staying in the jungle can bring. However, more remote experiences are a short drive away. Keep in mind this rental does not have a kitchen, but that means less time doing dishes and more time on the beach.
Cliff House with Stunning Pool, Spa, Ocean & Waterfall View - Maui
A private luxury residence in A’apali Ocean Outlookare, the Cliff House is a one-bedroom space for two that sits right atop the edge of a 300-foot-high cliff, providing a commanding view of the coast’s entire north shore all the way to distant Hana. Directly below are the Hanehoi Falls, spilling 150 feet into an oceanfront gorge. It’s hard to beat that view and you’ll also have your own private emerald-tiled pool tucked into a lush tropical setting and a hot tub that overlooks the coast, the Pacific, and the jungle. There’s practically an endless list of other notable features, including a poolside dining and barbecue area, an outdoor shower, a huge marble fireplace, and an entertainment center with Dish satellite TV with hundreds of music and movie channels, plus a DVD/CD player.
Ocean View Studio in Waikiki - Honolulu
Honolulu’s Waikiki Beach is certainly an iconic stop in Honolulu and appeals to travelers looking for more of a city experience. None the less, Waikiki Beach is striking, with turquoise waters that can be seen from this tiny but sleek apartment. Small and snug, the outdoor space will likely be the hangout spot for the duration of the stay.
Romantic Garden Cottage, View and Pool - Hanalei, Kauai
One of the best Airbnbs in Kauai, this cozy space is the perfect spot for romance, providing plenty of privacy tucked on an acre of “garden paradise” along the Wainiha River. From its vantage point on the bluff, you’ll enjoy magnificent views with beautiful beaches only a short drive away. After a day on the sand, you can look forward to swimming in your own private pool and a relaxing soak in the hot tub under the stars. A TV, Wi-Fi, full kitchen and washer/dryer are all included too.
Front Row Seats to the Lava Flow - Pāhoa
When dwelling in Kalapana, Hawaii, one doesn’t need any more than a tiny home, as the surroundings are the star of the show. While off the grid, guests are still treated to beautiful decor and hot water. Surrounding the home are papaya, bananas, pineapples, avocados, mango, dragon fruit and other delicious offerings. Being so close to the lava flow is quite thrilling as well!
