Hawaiian Villa Rentals | The Top 10 Luxury Vacation Rentals in Hawai'i
Come see why we choose these Hawaiian vacation rentals as the top 10 best vacation homes in Hawai'i!
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The Top 10 Luxury Vacation Rentals in Hawai’i

23 Aug 2019, Posted by Ashley in Blog

Why Choose Hawai’i as Your Vacation Destination?

Hawai’i is one of the most desirable destinations in the world, and is home to some of the
Top-Rated luxury vacation rental accommodations. Hawai’i has a lot to offer including the best weather conditions with steady temperatures and trade winds carrying the cool island breeze across the chain. Throughout the year the sun shines bright and the light rain showers keep the islands lush and vibrant. These factors and many more contribute to the perfect days here in Hawai’i that we call paradise.

You can find the best attractions and accommodations for Hawai’i on Oahu, Maui, the Big Island of Hawai’i, and Kaua’i. Discovering what these beautiful islands have to offer can be far less stressful when renting your own vacation home. You can truly experience local living walking to nearby farmers markets and grocery stores or riding bicycles around the neighborhood getting a good sense for the community that embraces you and your family. Not to mention the countless laughs, home cooked family dinners using delicious local produce and so many more fond memories you’ll be able to cherish forever.

Renting a vacation home allows for a unique experience away from the hustle and bustle of the resorts and crowds. Instead, you and your family can relax and enjoy the private pools and access secluded beaches right at your doorstep. You can take in the warmth from the sunshine, cool off in the enticing crystal blue waters, and gaze at the stunning views with your choice of company. What more can you ask for? Here are our Top 10 picks for Luxury Vacation Rentals on Hawai’i’s most beloved islands.

The Top 10 Luxury Vacation Rentals In Hawai’i

Royal Kailua Estate

This grand Estate is located on the Windward coast of O’ahu in the dream town of Kailua. This beautiful home is fashioned by the renowned designers Kerr-Michaels and is nearly 11,000 square feet. Royal Kailua Estate has a spectacular array of features including eight bedrooms and ten bathrooms. Not to mention the beach front property with private beach access and a private pool truly creates an oasis for families and groups to gather. The property is equipped with a gourmet kitchen, top of the line appliances, media room, and a cabana which is equipped with a fully stocked bar that looks over the pool and spa!
Link to Royal Kailua Estate booking details


Big Island Waterfalling Estate Big Island Waterfalling Estate sits on ten private acres located in Ninole, Hawai’i overlooking the Hamakua Coast. This magnificent Estate has five bedrooms and ten bathrooms truly catered to a once in a lifetime luxurious vacation experience. Features include an Olympic size swimming pool, a private nine-tee golf course, a tennis court that can also be converted into a basketball court, the world’s largest residential pneumatic elevator wrapped in Loui Vitton leather, and a rooftop lawn helipad. This property offers a stunning private triple decker waterfall in All rooms!
Link to Big Island Waterfalling Estate booking details


Obama Whitehouse Retreat
Named for its extremely famous guest who frequented this property on his winter vacations year after year during his time as Commander and Chief, the Obama Whitehouse Retreat is a true sanctuary with its spacious floor plan wrapped around the web of turquoise pools. This home is located in Kailua, O’ahu overlooking all of Kailua Bay and the Mokulua Islands. The hot tub spa is encircled with lava rocks, waterfalls, and stone bridges with lush greenery. The property is equipped with a gourmet kitchen featuring a full dining table out on the pool courtyard and five bedrooms with adjoining ensuite bathrooms. This estate is perfect for large families or groups vacationing together who want an exclusive vacation to unwind!
Link to Obama Whitehouse Retreat booking details



Banyan Hale is located on the Gold Coast of O’ahu nestled at the base of Diamond Head. This exclusive Hawaiian Estate includes seven bedrooms and eight bathrooms. This property is completely private offering a luxurious vacation experience with enticing tropical gardens, a lighted banyan tree providing adequate shade during the hot summer days. The lanais open out to the pool and spa, includes an open yard with a fire pit, and is just steps down from the ocean!
Watch the Video Tour Here
Link to Banyan Hale booking details


Wailele Villa
Wailele Villa is perched on the slopes of Diamond Head with a breathtaking 180 degree view of O’ahu’s South shore. This four bedroom, three bathroom home is ideally located near Waikiki home to some of Oahu’s best restaurants and world class shopping. Features include an indoor waterfall with tropical plants, a private lanai that opens up to the spa, and an upper master suite terrace. Just a ten minute walk from the beach and the home is equipped with top of the line appliances. Wailele Villa serves as a vacation haven for those in search of a quiet, peaceful retreat!
Link to Wailele Villa booking details here


Ocean House South
Ocean House South is an exquisite estate dripping in luxury and ocean views. This home is designed by renowned Hawaii Architect Jim Mcpeak who has truly created the epitome of a dreamhouse in paradise equipped with six bedrooms and seven bathrooms. This magnificent estate features an infinity-edge pool, jacuzzi, three-ocean view suites with ensuite bathrooms, and outdoor living areas. You can either wake up to ocean views or swim in the infinity-edge pool taking in the vibrant sunset views.
Link to Ocean House booking details


Kailua Sands Estate
Kailua Sands Estate occupies two private acres of beachfront property located in Kailua, O’ahu. This estate features two separate homes comprised of six bedrooms and six bathrooms offering inspiration adapted for relaxed, refined luxury living. The home is equipped with a fully stocked kitchen that includes a Wolf gas range, mahogany wood cabinets, and extensive granite counters. Within your own private resort-like compound is a 96,000 gallon lava rock swimming pool with cascading waterfall and grotto, water slide, and hot tub!
Link to Kailua Sands Estate booking details


Maui Black Rock Estate
Maui Black Rock Estate is ideally located in Ka’anapali, Maui on the West side of the island. This estate is equipped with eight bedrooms and nine bathrooms that can accommodate up to 16 guests perfect for large families or groups traveling together. This home includes a spacious gourmet kitchen, two private dens, a game room with a ping-pong table, and a billiards room with a pool table. Not to mention a library and wet bar, private indoor gym, a secure three-car garage, and tarmac for your own use. This property includes a designated outdoor grilling area,private cabana, swimming pool, and jacuzzi spa area. Enjoy all the amenities from nearby Ka’anapali Beach Resort, Whalers Village, and a surplus of West Maui activities!
Link to Maui Black Rock Estate booking details


Maui Shambala Tropical Estate
Maui Shambala Tropical Estate is located in Wailea, Maui on the South side of the island. This beautiful home has six bedrooms and nine bathrooms with 11,000 square feet of living space equipped with panoramic ocean views spread over two acres of land. The home is equipped with a double kitchen with duplicate appliances, 180 bottle wine closet, sunken tiered living room, and sixteen TV’s for your personal use. This property features three heated pools, waterfalls, cascading hot spa, four-hole golf course on site, private gym, and a children’s playroom. This estate is not only captivating, but has a sense of peacefulness, tranquility, and calm serenity that you will feel when walking through the private gardens or relaxing by the warm pools!
Maui Shambala Tropical Estate booking details


Hale Lanikai
Hale Lanikai is located on the beloved Lanikai Beach in Kailua, O’ahu. This charming Hawaiian style home has four bedrooms and four bathrooms with an additional Ohana unit that ideal for a family vacation and gathering place for friends. The property is equipped with a fully stocked and upgraded kitchen, an idyllic outdoor space with an ocean deck, and private beach access to one of the best beaches in the world! Stunning views of the ocean, mountains, beach, and Mokulua Islands make this an unforgettable escape!
Link to Hale Lanikai booking details