10 Airbnb Rentals in Hawaii That Will Cost You at Least $4,500 per Night



The islands of Hawaii are known for their natural beauty and abundance of outdoor activities for visitors to enjoy. Whether you’re looking for some rest and relaxation or you want an active getaway, Hawaii has something for you.

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You really can’t go wrong when choosing where to stay; but, if you want the privacy of your own space, an Airbnb is a great option. And if you have a sizable travel budget, you can stay at some of the most luxurious rentals available.

Here’s a look at the most luxurious Airbnbs in Hawaii, listed from least to most expensive.


Plantation at Paradise Point, Kailua

  • Nightly rate: $4,500

This five-bedroom, 5.5-bathroom secluded beach house has served as a vacation home for former President Barack Obama and his family. It features a fully equipped fitness room, a heated lagoon pool, a waterfall, a hot tub and a poolside lanai.

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Contemporary Resort Villa on the Links, Kailua-Kona

  • Nightly rate: $4,564

This three-bedroom, 3.5-bathroom contemporary resort villa is located by the golf course at Hualalai Resort. In addition to easy access to the links, this private getaway features a heated swimming pool and hot tub, ocean views and two golf carts to easily get around the property and resort.


Tropical Villa on the Pacific, Kohala Coast

  • Nightly rate: $5,900

Located on the grounds of the Mauna Lani resort, Halekailani sits on an acre of ocean-front property and provides all of the benefits of indoor-outdoor living. The five-bedroom, 8.5-bathroom villa boasts a number of luxurious amenities, including a media room, a fully equipped home gym, a sauna and multiple swimming and spa options. A 24-hour villa manager and concierge services are all included as well.


Dali Hale Estate on Secret Beach, Kilauea

  • Nightly rate: $6,000

The Dali Hale Estate features seven bedrooms and 7.5 bathrooms on a 6,000-square-foot property. Located on the bluffs above Kauai’s North Shore coastline, the villa offers panoramic views of the tropical mountains, the Pacific Ocean and the iconic Kilauea Lighthouse. Amenities include a pool, hot tub, outdoor showers and a tennis court. Plus, it’s a quick five-minute walk to Secret Beach.

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Haiku House Maui, Haiku-Pauwela

  • Nightly rate: $6,600

The nine-bedroom, 10.5-bathroom Haiku House Maui is surrounded by lush greenery and features ocean views. Enjoy the home as is, or add on extra services to up the luxury factor — a private driver, villa manager, private chef and spa services are available at an additional cost.


Kahua Kohola Estate, Kailua-Kona

  • Nightly rate: $6,611

Enjoy the natural beauty of the Big Island at the Kahua Kohola Estate, which can accommodate up to 10 guests across the five-bedroom, 5.5-bathroom property. Amenities and services include a heated pool and hot tub, ocean views, daily housekeeping and a villa manager.


Luxury Stay in Waimea

  • Nightly rate: $7,495

Kahieluana is a five-bedroom, six-bathroom seaside villa that can accommodate up to 14 guests. Those who love to stay active will find plenty to do at this modern retreat, as the property features a heated swimming pool, tennis court, bocce ball court and a volleyball court; plus, it has all of the equipment you need to take advantage of the beach, including a stand-up paddleboard, boogie boards, snorkeling equipment and a kayak.

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Espacio Waikiki Penthouse, Honolulu

  • Nightly rate: $8,557

Located just a quick walk from Waikiki Beach, the Espacio Waikiki Penthouse features two bedrooms and two bathrooms and all of the amenities you’d expect from a luxury stay. This includes twice-daily housekeeping, butler service and daily use of a Mercedes-Benz GLC300.


The Sullivan Estate, Haleiwa

  • Nightly rate: $14,200

Spa lovers should book their stay at The Sullivan Estate, which provides access to a spa retreat hosted by the skincare brand JK7. Guests can enjoy private yoga lessons, sauna sessions, massages, facials and organic cuisine. The oceanfront property on Oahu’s North Shore features six bedrooms and 5.5 bathrooms.


Kauhale Pilialoha, Waimea

  • Nightly rate: $18,500

Located on the Mauna Kea Resort along the northwest coast of Hawaii’s Big Island, Kauhale Pilialoha features 10 bedrooms, 14 bathrooms and no shortage of ocean views. The villa is comprised of four separate houses and plenty of top-of-the-line amenities, including an infinity swimming pool and hot tub, game room, home theater, spa facilities and a large outdoor entertainment area with its own Tiki bar and table with seating for 26.

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Prices are accurate as of Sept. 22, 2022, and are subject to change.