From the highest end, at a breathtaking $8000+ a night, to the relative low budget of $155 for a surfing-inspired room, there is a modern rental accommodation option to suit every budget, allowing everything that this magnificent dream destination has to offer. Here's a selection of some of our favorite options.
Royal Beach Estate, Oahu
The 7 bedroom, 7.5 bath Royal Beach Estate is one of the newest, most striking and contemporary executive beachfront estates on world-renowned Kailua beach. Constructed in 2008, the estate features two homes (main house and guest house) separated by a resort-style pool with elegant umbrellas and lounge furnishings. Rental will set you back $8,665 per night for up to a maximum of 18 guests!
The Obamas’s first rental choice—where they stayed in 2009 and 2010—is impressive. The Plantation Estate, unofficially known as the "Winter White House", opens up to a lagoon-style pool in the front courtyard with cascading waterfalls and a lavish heated spa.
At $3,400 per night, The Palm Beach House is a spacious 6 bedroom, 6 bath luxury estate placed right on Kailua Beach. Enjoy the gorgeous central lava rock pool and tropical courtyard or step from the yard onto the sands of world famous Kailua Beach.
This spectacular three bedroom, three and a half bath, 3,500 square foot, two level home is nestled on the South side of Hoolei, on a very private quiet cul-de-sac bordered by the Wailea Blue Golf Course and a lush green belt slope. As you gaze across the green belt, the view of the deep blue Pacific Ocean view is breathtaking. Between the palms, waves gently break on one of the best beaches in the world.
Rainbow Estate is a luxurious vacation rental located in Maui, hosting gorgeous Pacific Ocean views. This four bedroom estate has an ability to sleep up to 10 guests in comfort, surrounded by a host of fun vacation amenities. The king master suite is divine with a deluxe en suite bathroom and complete privacy. The two private queen suites are lovely and share a luxurious bathroom. The fourth bedroom is loft-style with two double beds; perfect for children, and adjacent to the indoor movie theater.
If you are traveling on a much more modest budget, look no further than this part fairy cottage, part hippie hideaway. This little house is tucked away in a lush Hawaiian garden. Perfect for unwinding.
Enjoy a week or two in paradise in this modern private screen house floating in the embrace of three spectacular monkeypod trees. Located 45 minutes south of Hilo in the Puna district, Hale ‘Ohai is an elegant sanctuary, a place to rest and reflect, a place to gather for special occasions, a place from which to explore and discover the Big Island of Hawaii.
Drive down the driveway, past an enormous banyan tree, to this large home. This classic Hawaiian home, with its original lava rock wall entrance, is the main house on one of east Oahu's larger ocean front properties. It has been remodeled, while maintaining its original Hawaiian charm.
No trip to Hawaii is complete without exploring the surfer culture and lifestyle, or even having a go yourself at this "sport of kings", which originated itself on the islands. If you want to stay in a place that embodies all the charm and energy of the North Shore lifestyle, this 1 bedroom 1 bath, with enclosed, spacious lanai is the perfect place to get away from it all. If you happen to like some turf with your surf, the apartment looks out to the renowned Arnold Palmer 19-hole golf course and a charming cluster of mature banyan trees.
In case you are inspired to settle for good into the dreamy Hawaiian lifestyle, why not just top-out and buy at the highest end of the market? While the Big Island is usually no. 1 on the "Best Islands to Live On" annual ranking, this $28 million, 6,600-square-foot home on the west side of the Big Island is listed as the third most expensive home for sale on the island. If you can "settle" for five beds, six baths and views from your pool that will make you weep with joy, this house is worth it.