The 9 Best Hawaii Vacation Rentals of 2019

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Our Top Picks

Best Beachfront: Book Lalamilo Beach Bungalow at Airbnb "Located right on the sand, offering direct access to activities like swimming, snorkeling, and surfing."

Best Jungle Stay: Book Eco Hale Hawaii at Airbnb "Perfect for travelers interested in adventuring through or relaxing in nature."

Best in Waikiki: Book Beachfront Condo in Waikiki Beach at Airbnb "The spacious, modern apartment has two patios for sweeping views of both Honolulu and the ocean."

Best Luxury: Book Kohola Point Villa at Airbnb "Though the home is quite sprawling, it still feels cozy and intimate."

Best near Volcano: Book Lava Flow House at Airbnb "With a stay in this Pāhoa home, you’ll be living right on an old lava flow."

Best for Families: Book Princeville Family Retreat at Airbnb "The bright, airy home with beachy decor is perfectly suited to cater to groups."

Best for Romance: Book Star Lookout at Airbnb "It’s a perfect spot for a romantic getaway with an outdoor shower, a private hot tub, and fresh flowers and fruit."

Best Bungalow: Book Magical Bohemian Retreat at Airbnb "This bohemian-chic guest suite is all about being outside."

Best Treehouse: Book Kukui Treehouse at Airbnb "Live out your childhood fantasies by booking a stay at this treehouse."

Our Top Picks

01 of 09

Best Beachfront: Lalamilo Beach Bungalow

Lalamilo Beach Bungalow

Airbnb

Bedrooms (3)

  • 6 guests

  • 1 King bed

  • 1 Double bed

  • 2 Single beds

Amenities

  • Wi-Fi

  • Barbecue

  • Private Patio

  • Washer/dryer

With more than 100 beaches in the Hawaiian Islands, their white (and sometimes black) sands are big drivers of tourism to the state. Indulge in one of them at the Lalamilo Beach Bungalow on Waialea Beach on the Big Island. The historic home, which is nearly a century old but perfectly updated, is right on the sand, offering direct access to activities like swimming, snorkeling, and surfing. Along with three bedrooms, the property has large kitchen, dining, and living areas, as well as two detached bathrooms. There's even a private patio and lawn for taking in beautiful ocean views. You’ll definitely need a car to get around here — the location is relatively secluded, which is part of its appeal.

02 of 09

Best Jungle Stay: Eco Hale Hawaii

Eco Hale Hawaii in the Rainforest

Airbnb

Bedroom (1)

  • 2 guests

  • 1 Queen bed

Amenities

  • Wi-Fi

  • Hot tub

  • Free breakfast

  • Beach equipment

If you're drawn to the jungles of Hawaii, consider booking a stay in an eco-friendly home like this one, which is set on one acre amid plenty of Hawaii’s native greenery. Adding to the eco-conscious mindset, the property runs on solar power and features sustainable bamboo flooring, custom tile pieces, and re-purposed materials. This charming off-the-beaten cottage is halfway between Hawaii Volcano National Park and the town of Hilo on the Big Island, and it’s perfect for travelers interested in adventuring through or relaxing in nature. Take off on an adventure through the national park during the day, then unwind in the home’s outdoor Japanese hot soaking tub at night. 

03 of 09

Best in Waikiki: Beachfront Condo in Waikiki Beach

Beachfront Condo with Resort Access

Airbnb

Bedrooms (3)

  • 8 guests

  • 1 King bed

  • 2 Double beds

  • 2 Single beds

Amenities

  • Wi-Fi

  • Air conditioning

  • Washer/dryer

  • Pool

For a more personalized take on a hotel stay, book this three-bedroom condo set right on Waikiki Beach in Oahu. The spacious, modern apartment has two patios for sweeping views of both Honolulu and the ocean. There's also free parking and an elevator at the property. What sets this rental apart from others is its access to the facilities at the neighboring Outrigger Reef Hotel, including the pools and hot tubs, the spa, and the restaurants. While you’ll likely want to spend most of your time at the beach, you’re also within walking distance of all of Waikiki’s shopping, dining, and entertainment.

04 of 09

Best Luxury: Kohola Point Villa

Kohola Point

Airbnb

Bedrooms (4)

  • 8 guests

  • 3 King beds

  • 1 Queen bed

Amenities

  • Pool

  • Hot tub

  • Surround sound system

  • Barbecue

This four-bedroom clifftop property in the gated neighborhood of Anini Vista near Hanalei Bay in Kaua’i is one of the top luxury rentals on the island — and for good reason. Though the home is quite sprawling, using an indoor-outdoor style that optimizes ocean views across the infinity-edge pool and hot tub, it still feels cozy and intimate, thanks to the wood elements that bring a natural touch to the decor. As an Airbnb Luxe property, guests can request services and staff like a private chef, airport transfers, and in-home spa treatments. The house is within a short drive of beaches, golf courses, and the towns of Princeville and Hanalei, where you’ll find restaurants and shops.

Continue to 5 of 9 below.
05 of 09

Best near Volcano: Lava Flow House

Lava Flow House

Airbnb

Bedrooms (4)

  • 11 guests

  • 3 King beds

  • 1 Queen bed

  • 1 Double bed

Amenities

  • Pool

  • Beach gear

  • Barbecue

  • Wi-Fi

One of Hawaii’s other claims to fame is the active volcanoes. With a stay at the Lava Flow House in Pāhoa on the Big Island, you’ll be living right on an old lava flow. While the vast field of black volcanic rock provides a fascinating sight from the strikingly modern, high-end home, you’re actually located near active lava from Kilauea, and you can hike out to a safe viewing point. You can also hike to a black-sand beach directly from the house. For entertainment, the village of Pāhoa’s restaurants and shops are just a short drive away.

06 of 09

Best for Families: Princeville Family Retreat

Princeville Family Retreat

Airbnb

Bedrooms (4)

  • 12 guests

  • 3 King beds

  • 2 Single beds

Amenities

  • Wi-Fi

  • Washer/dryer

  • Foosball table

  • Beach equipment

If you’re heading to Hawaii with the family in tow, you’d do well to book this four-bedroom home in Princeville on Kaua’i, just half a block from the ocean and the town’s famous Queen’s Bath tidepool. The bright, airy home with beachy decor is perfectly suited to cater to groups, with four bedrooms, a game room with foosball, kid-friendly toys both inside and in the backyard, and beach equipment like snorkeling gear, boogie boards, and beach chairs. The Airbnb Plus home is within a 15-minute drive of famous Hanalei Bay, numerous beaches, restaurants, and golf courses.

07 of 09

Best for Romance: Star Lookout

Star Lookout

Airbnb

Bedrooms (1)

  • 2 guests

  • 1 King bed

Amenities

  • Private hot tub

  • Shared pool

  • Outdoor shower

  • Wi-Fi

Experience “old Hawaii” with a stay in this cozy jungle bungalow in Huelo, a small village on the Road to Hana. It’s a perfect spot for a romantic getaway, with an outdoor shower, a private hot tub, and fresh flowers and fruit provided for your stay. There’s also a pool that’s shared with another guest house, though there’s a chance you’ll have it to yourselves. The cottage, an Airbnb Plus property, is located just a 20-minute drive from Paia and Makawao, two communities with shops and restaurants, and a 45-minute drive from Kihei, which is known for its beaches.

Check out other options with our selection of the best Maui vacation rentals.

08 of 09

Best Bungalow: Magical Bohemian Retreat

Bohemian Retreat on a Mango Farm

Airbnb

Bedrooms (2)

  • 4 guests

  • 1 King bed

  • 1 Queen bed

Amenities

  • Wi-Fi

  • Smart TV

  • Washer/dryer

  • Hammock

For those who love nature just as much as they love creature comforts, consider this vacation rental. Located on a working mango farm in Captain Cook on the Big Island, this bohemian-chic guest suite is all about being outside — while all the spaces have roofs overhead, they’re each quite open to the outdoors, from the patio-like living room and full kitchen to the two screened-in bedrooms to the open-air bathhouse. The location is also ideal, as it's just a mile from Kealakekua Bay and the local restaurants of Captain Cook.

Continue to 9 of 9 below.
09 of 09

Best Treehouse: Kukui Treehouse

Kukui Treehouse

Bedroom (1)

  • 2 guests

  • 1 King bed

Amenities

  • Full kitchen

  • Outdoor shower

  • Hot tub

  • Shared laundry facilities

Live out your childhood fantasies by booking a stay at this 500-square foot, indoor-outdoor style treehouse. It’s a totally luxurious stay, complete with a full kitchen, a bedroom with incredible ocean views, a lanai, and a hot tub. The treehouse is set on a three-acre farm at 1,800 feet of elevation (meaning the weather is a bit cooler than what you’d find at sea level), located just a 15-minute drive from downtown Kona on the Big Island.

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