10 Best Luxury Rentals in Hawaii

The truth is that Hawaii is on just about everyone’s bucket list. Who doesn’t want the aloha spirit and stunning beaches? Not forgetting the exciting activities and beautiful luxury vacation rentals. Reasons Hawaii is continually rated as a top vacation destination. Plus, it’s also the perfect place to relax, unwind, and disconnect from your daily routine. However, if you need a nudge to visit this island destination we’ll give you more than that. Hawaii is made up of eight main islands, all of which are unique in their own way.

“The Gathering Place,” is the most famous of all eight islands, with a little bit of everything for everyone. From Honolulu to the quiet shores of the east side. Hawaii island is known for its volcanoes and lava! It is the youngest of all the islands and is currently still growing. If you are looking for some more private and hippie vibes, Kauai is perfect for you. Known for its colorful and lush vegetation, and amazing hiking. It is the oldest of all the main islands and is heaven on Earth. Expect private white beaches, blue water, and fantastic views of the mountains wherever you are.

Hawaii is the most diverse state and is a melting pot of all cultures, finding a variety of influences from, Hawaiian culture, as well as Chinese, Japanese, Korean, Thai, Portuguese, Samoan, Tahitian, Tongan, Micronesian, and Spanish—and the list goes on.

Hulalai Estates - Kailua, Hawaii

This luxury and beautiful villa is located in within Hualalai Resort, the finest property bordering the resort's golf course, the 6,300-square-foot home offers expansive outdoor living areas, spacious and elegant interiors, and panoramic views of the lush fairways, Pacific Ocean, and Hawaiian sunset. on the Big Island of Hawaii, an easy walk from the beachfront Four Seasons. Hualalai Estates provides exquisite privacy while placing you in the heart of one of the finest oceanfront resorts in the world, with amenities suited for guests of all ages.

Five bedrooms include four large king suites (one of which is located in a separate cottage), making Hualalai Estates an ideal vacation rental for family reunions, destination wedding guests, and groups of friends up ten in size. The bedrooms include four fabulous king suites and guestroom with two twin-size beds. The three main-house king suites and the cottage suite opens to the villa's terrace, and all five rooms enjoy en-suite bathrooms and open-air showers like rain forest cascades. There are gorgeous stone bathtubs in the master bath and the primary guest bath, as well. This house is up for 10 guests having 5 bedrooms and 5.5 bathrooms starting at 9,300 USD per night, for more information you can access Cuvee.com.

Thousands Waves - Maui, Hawaii

This stunning Maui vacation rental delivers postcard-perfect views of palm trees, the Pacific and neighboring islands from an oceanfront location on the west coast near Ka’anapali. With 11,000 square feet and eight bedrooms, there’s enough space for parties of up to sixteen friends or family members.

At the heart of the villa, you will find a double-height glass wall that can be opened making and indoor-outdoor living space. Let the warm tropical breezes flow over a living room, dining area, and fully equipped kitchen, all filled with refined island-inspired furnishings and warm wood paneling. On the warmest days, you can opt to close off the space and flip on the air conditioning.

Thousand Waves has four bedrooms with king beds, including a honeymoon-worthy master suite with its own jetted tub, lanai, and ocean views. There are also two bedrooms with queen beds and two bedrooms with two queen beds each. All eight bedrooms have en-suite bathrooms. More information at Luxuryretreats.com, starting at 13,100 USD per night.

Kahua Kohola Estate - Kona, Hawaii

Private and luxurious, the perfect definition for this villa. With spacious ocean-view living areas and five-star resort amenities, you will also find plenty of places to gather together. Face off in friendly competitions on the tennis court or golf course. Schedule time together at the open-air spa.

This 5-bed, 7-bath escape wasn’t just built on the island—it was created from it. With natural beeswax and island stone-clad walls, Hawaiian spirit comes to life.

The line between a dream and real life it will be very close when you see the infinity pool and hot tub—both just steps from open lounge area seating, counting with an interior courtyard with koi pond. Lush gardens, a covered patio, and the master bathroom’s deep soaking tub complete the paradise. You can find this property on Covee.com with a price upon request.

Royal Kailua Estate - Kailua, Hawaii

Royal Kailua Estate is a spectacular beachfront villa on Oahu, featuring panoramic ocean views and direct access to Kailua Beach. The palatial, 11,000-square-foot home is ideal for large families or groups of friends, with expansive outdoor living areas, beautifully furnished interiors, and extraordinary amenities for dining, relaxation, and fun. Five bedroom suites in the main house plus a three-bedroom guest house accommodate sixteen guests in total comfort.

The main house includes five bedroom suites, two of which you can easily enjoy the gorgeous ocean view. The master suite boasts a privileged corner position with expansive vistas, and features a walk-in closet, private sitting area, and deluxe bathroom with steam room and jetted tub. The guesthouse includes two king suites and a queen suite, as well as a private living area with a dining table and kitchenette. All of the villa's bedrooms enjoy ensuite bathrooms. Royal Kailua Estate is the crown jewel of Kailua beachfront property. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green lawn, scattered coconut trees, and luxurious guest house. For more information, you can go to Evrhi.com, price upon request.

Kauhale Pilialoha - Waimea, Hawaii

Kauhale Pilialoha, a majestic oceanfront villa located at Mauna Kea Resort, along the northwest coast of Hawaii's Big Island. Comprising four distinct houses on a large, 2.5-acre private property, offering an unforgettable luxury destination for a family reunion, inspiring retreat, or unforgettable vacation with friends. Including amenities like infinity swimming pool and hot tub, game room, home theater, spa facilities, and an expansive alfresco entertainment area with vintage Tiki bar and table for twenty-six. Each of the private villas includes its own amenities and living areas, forming an ideal haven for multiple families or destination wedding guests.

The Kilohana Koholo villa houses the master suite, while the three guest villas—Mango, Koa, and Bamboo—include three bedrooms each. The master suite features a large, custom-built king bed, kitchenette, office, and fabulous ensuite bathroom with three bathtubs (including a hot tub). All of the guest suites enjoy ensuite bathrooms and outdoor lanais or lounge areas. More information at luxuryretreats.com starting at 15,000 USD per night.

Royal Ilima - Wailea, Hawaii

Steps to the serene and private Wailea Beach, guests have access to their own sun loungers and Wailea Beach Villas infinity pool, hot tubs and fitness suite. Maui’s famously perfect beaches are all a short walk or drive, including, the famous Oneloa “Big Beach” and Kamaole “Kam” One Beach. Resorts close by including the Four Seasons Resort Maui at Wailea and the Fairmont Kea Lani which feature World-Class dining.

This 3-bedroom luxe residence provides panoramic ocean views and true indoor/outdoor living. Enjoy relaxing after a long day on the island in this tropical oasis. Steps from Wailea Beach, guests can access Wailea Beach Villas World-Class amenities, including infinity pools and gym. More information in Cuvee.com, price upon request.

Moana Lani - Honolulu, Hawaii

Guaranteeing memories to last a lifetime, Oahu is the heart of the Hawaiian islands and a natural gathering point for its people; an ideal embraced by the villa’s communal feel, spacious grounds, and active outlook. Moana Lani, a private, luxurious 5-bedroom home set along Oahu’s majestic south coast. Enjoy breathtaking Pacific views and take advantage of the home’s waterfront access for snorkeling and kayaking adventures.

This luxury vacation rental has five air-conditioned bedrooms. Upstairs, you’ll find the Master suite and first guest bedroom, both looking out to spectacular ocean views. The Master suite features its own private balcony. Each room in the main house contains its own exquisite ensuite bathroom, with premium fittings and fixtures. A fifth, King bedroom resides in the guest house, with access to its own bathroom. More information Luxuryretreats.com starting at 3,000 USD per night.

Hekili Point - Lahaina, Hawaii

A holiday on the west coast of Maui means stunning views, laid-back beaches, incredible snorkeling, and a surprising array of shopping and dining. This luxury Maui vacation rental was Inspired by traditional kama’aina architecture and has more than 9,000 square feet of living space laid out around a pool and garden. Peaceful oceanfront setting in Olowalu, just south of Lahaina, affords sweeping views of the West Maui Mountains, Molokini and Kahoolawe, and sunsets over Lanai.

Hekili Point was designed by award-winning architect Glenn Mason, an expert in heritage preservation, to combine authentic 1930s details with state-of-the-art smart-home technology. There are three bedrooms in the main house, including one with a king bed and kitchenette, and two with queen beds. The fourth bedroom is a honeymoon-worthy freestanding master suite with a king bed, al-fresco shower and its own entrance, linked to the main house by a walkway. All four bedrooms have en-suite bathrooms. For more information go to Villaway.com starting at 3,250 USD per night.

Surf’s up Hale - Waimea, Hawaii

Surf’s Up Hale is a luxury property—a beachside paradise on Big Island that looks as if sculpted by the goddess. From flowing magma and snow-capped mountain peaks to lush green rainforests, this magical oasis of the Pacific shows you the beauty of nature’s determination. The waterfall feature and landscaping at this lovely villa are subtle reflections of this biodiversity.

Surf’s Up Hale is furnished for a breezy contemporary lifestyle. Every room features original works of art that add a sense of levity. The estate is a smart house with Lutron lighting, seven large flat-screen televisions, and indoor/outdoor surround sound. The gourmet kitchen is a chef’s delight. Four resplendent bedroom suites accommodate up to eight guests at Surf’s Up Hale. You will find two Master Suites with access to a covered lanai with an ocean view. All suites include televisions, ceiling fans, and king beds. For more information enter luxuryretreats.com starting at 3,850 USD per night.

Villa Luana - Honolulu, Hawaii

Villa Luana provides an ideal setting for relaxing in blissful comfort. With several living spaces, a gourmet kitchen, and a large dining area, this elegant home perfectly accommodates everything from multi-generational families to corporate retreats. For added flexibility, it offers an attached cottage with its own living room and full kitchen.

Villa Luana’s spacious living areas feature upscale furnishings and luxury finishes such as natural limestone and hardwood flooring. Even the most discerning chef in the group will appreciate its modern, well-appointed kitchen. From sumptuous bedrooms and spa-like bathrooms to private office space to an ocean-view reading nook, this home’s endless amenities will exceed your expectations. The heart of Villa Luana is a pool courtyard that feels like your own luxury resort, from the waterfall feature in the pool itself to the loungers and shaded sitting area. Soak in the sun from a separate lanai, serve local seafood from the barbecue and watch the stars come out from the upper-level deck. Up for 16 guests, with 6 bedrooms, for more information at Evrhi.com, price upon request.