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Luxury Vacation Rentals in Hawaii

Indulge in the ultimate Hawaiian escape with our handpicked collection of luxury vacation rental properties across the islands. Whether you're seeking an elegant oceanfront estate, a secluded mountain retreat, or a resort-style villa with world-class amenities, we have the perfect home for your dream getaway. Explore our most exclusive listings on each island: discover stunning Oahu luxury villas, breathtaking Maui luxury estates, serene Kauai beachfront homes, and extraordinary Big Island vacation retreats. Each property is carefully selected for its comfort, style, and unforgettable views. Whether planning a family celebration, honeymoon, or wellness escape, you’ll find island elegance at its finest. Browse more exclusive villas below and start planning your luxury Hawaii experience today!

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Luxury 3BR Kailua-Kona Vacation Home with Ocean Views
Luxury 3BR Kailua-Kona Vacation Home with Ocean Views
Luxury 3BR Kailua-Kona Vacation Home with Ocean Views

Luxury 3BR Kailua-Kona Vacation Home with Ocean Views

Escape to the breathtaking beauty of the Big Island and indulge in a luxurious stay at this stunning 3-bedroom, 2-bathroom vacation rental home nestled in the heart of Kailua-Kona. This tropical paradise offers an open, spacious interior filled with all the comforts of home, making it an ideal retreat for families and groups of friends seeking both luxury and convenience.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $530 
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Luxury Ko Olina Golf Estate with Beach Access
Luxury Ko Olina Golf Estate with Beach Access
Luxury Ko Olina Golf Estate with Beach Access

Luxury Ko Olina Golf Estate with Beach Access

This stunning two-story estate is situated within the gated Ko Olina Kai Resort Community, offering over 2000 sq. ft. of elegant living space. Perfect for vacationers or business travelers, it combines comfort and style with first-class furnishings and timeless décor.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kapolei
from $615 
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Luxury Kailua Beach Estate with Ocean Views
Luxury Kailua Beach Estate with Ocean Views
Luxury Kailua Beach Estate with Ocean Views

Luxury Kailua Beach Estate with Ocean Views

Welcome to Ranch Beach Estate, a hidden gem just steps from Kailua's pristine white sand beaches. Nestled on a coveted loop, this luxurious home offers easy access to local cafes, boutiques, and farmers' markets. A manicured grass driveway with fragrant plumeria and a salty breeze invites you into a private, fully-fenced tropical oasis.

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua
from $937 
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Niu Beach Estate – Private Luxury Meets Island Sophistication
Niu Beach Estate – Private Luxury Meets Island Sophistication
Niu Beach Estate – Private Luxury Meets Island Sophistication

Niu Beach Estate – Private Luxury Meets Island Sophistication

This luxurious Niu Beach Estate offers a private, modern retreat on Oahu's southern shores. With five bedrooms and five and a half bathrooms, this beautifully remodeled plantation-style home blends contemporary design with tropical elegance.

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $2,965 
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Charming 1BR Maui Condo Near Beach & Shops
Charming 1BR Maui Condo Near Beach & Shops
Charming 1BR Maui Condo Near Beach & Shops

Charming 1BR Maui Condo Near Beach & Shops

Escape to Maui and stay in this beautifully remodeled 1-bedroom, 1-bath condo located in the heart of Kihei. This island oasis offers convenience and comfort, with everything you need just steps from your door.
Enjoy easy access to Maui’s stunning beaches, including one of the largest in the island, perfect for morning walks or sunset evenings.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kihei
from $594 
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Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!
Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!
Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!

Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!

Paradise found! This beautiful, new home is situated off a paved road behind a solar powered entry gate, on 3 gorgeous acres. You will feel relaxed the moment you arrive, from our comfortable and welcoming fully furnished lanai to the spacious and well appointed interior.

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Keaau
from $715 
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The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood

The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood

The Kahala Mansion offers a luxurious, private escape on Kahala Avenue, just steps from the beach. This grand estate features expansive indoor and outdoor living spaces, lush courtyards, and elegant accommodations. Perfect for serene retreats, grand celebrations, or corporate events, the property combines architectural brilliance with resort-style amenities including a private pool, entertainment center, and dedicated concierge services.

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $7,107 
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Waialua Beachfront Estate – Tranquil North Shore Getaway with Ohana Charm
Waialua Beachfront Estate – Tranquil North Shore Getaway with Ohana Charm
Waialua Beachfront Estate – Tranquil North Shore Getaway with Ohana Charm

Waialua Beachfront Estate – Tranquil North Shore Getaway with Ohana Charm

This stunning beachfront property in Waialua on Oahu's North Shore offers a perfect blend of luxury and comfort for long-term stays. The main house features an open-concept kitchen with high-end stainless steel appliances, extensive counter space, and bar seating, ideal for preparing meals and entertaining.

  • 9 bedroom
  • 6 bathroom
  • Sleeps 14
Hawaii> Waialua
from $2,176 
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Luxurious Kauai Vacation Home with Mountain Views
Luxurious Kauai Vacation Home with Mountain Views
Luxurious Kauai Vacation Home with Mountain Views

Luxurious Kauai Vacation Home with Mountain Views

Discover the charm of Laulea Hale, a beautifully designed vacation home nestled in a quiet cul-de-sac in Princeville, Kauai. Perfect for families or groups, this spacious 4-bedroom, 5-bathroom residence comfortably hosts up to 10 guests, offering a blend of style, comfort, and island tranquility.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Princeville
from $811 
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Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast

Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast

This stunning beachfront estate in Kahala offers the perfect blend of modern luxury and old Hawaiian charm, ideal for large groups seeking privacy and comfort. Located directly on Kahala Beach, the property features seven air-conditioned bedrooms, each with California king beds, en suite bathrooms, and smart TVs.

  • 7 bedroom
  • 8 bathroom
  • Sleeps 14
Hawaii> Honolulu
from $6,147 
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Luxury Oceanview Estate at Mauna Kea Residences
Luxury Oceanview Estate at Mauna Kea Residences
Luxury Oceanview Estate at Mauna Kea Residences

Luxury Oceanview Estate at Mauna Kea Residences

This stunning single-level gated estate offers breathtaking ocean views and luxurious island living. The spacious sunken great room features sliding glass pocket doors that seamlessly connect indoor and outdoor spaces, perfect for relaxing or entertaining.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kamuela
from $2,649 
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Turtle Bay Fairway Condo - Kuilima Estates East
Turtle Bay Fairway Condo - Kuilima Estates East
Turtle Bay Fairway Condo - Kuilima Estates East

Turtle Bay Fairway Condo - Kuilima Estates East

Welcome to your North Shore paradise! This fully remodeled Turtle Bay condo offers breathtaking views of the 18th hole through expansive wall-to-wall windows. Guests enjoy access to two private pools, tennis and pickleball courts, and over 5 miles of pristine beaches just minutes away.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kahuku
from $742 
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Luxury North Shore Estate for 40+ Guests
Luxury North Shore Estate for 40+ Guests
Luxury North Shore Estate for 40+ Guests

Luxury North Shore Estate for 40+ Guests

Welcome to the premier property on the North Shore capable of hosting over 40 guests in a stunning, private setting. This half-acre estate features five separate units, each with three bedrooms and one bathroom, offering ample space for large gatherings such as family reunions, destination weddings, business retreats, or special events.

  • 15 bedroom
  • 5 bathroom
  • Sleeps 48
Hawaii> Hauula
from $2,635 
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Luxury Oceanfront Architectural Estate in Honolulu
Luxury Oceanfront Architectural Estate in Honolulu
Luxury Oceanfront Architectural Estate in Honolulu

Luxury Oceanfront Architectural Estate in Honolulu

Experience the ultimate luxury in this exclusive oceanfront estate in Honolulu, a true architectural marvel that has hosted icons like Frank Sinatra, Elvis Presley, and Paul McCartney, who composed "Silly Love Songs" here. This 30-day minimum rental offers unparalleled privacy and spectacular 180-degree ocean views, making it ideal for those seeking a unique and memorable getaway.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,488 
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Hale Lani – 5BR Estate at Hualalai Resort
Hale Lani – 5BR Estate at Hualalai Resort
Hale Lani – 5BR Estate at Hualalai Resort

Hale Lani – 5BR Estate at Hualalai Resort

Discover this exceptional five-bedroom, five-and-a-half-bathroom Hawaiian estate that embodies the true spirit of island paradise. With dramatic 180-degree views of the ocean, fairway, Maui, and breathtaking sunsets, this custom-built residence offers the perfect blend of luxury and natural beauty.

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $10,355 
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Luxury Oceanfront Samurai House in North Shore Oahu
Luxury Oceanfront Samurai House in North Shore Oahu
Luxury Oceanfront Samurai House in North Shore Oahu

Luxury Oceanfront Samurai House in North Shore Oahu

Welcome to Samurai House by Gather, a luxurious Japanese-inspired estate perched on a dramatic oceanfront point on Oahu's North Shore. This exclusive 4-bedroom plus bunk area, 6-bathroom property offers a perfect blend of elegant design, modern amenities, and breathtaking natural beauty, ideal for family vacations, group retreats, or special celebrations.

  • 5 bedroom
  • 8 bathroom
  • Sleeps 11
Hawaii> Haleiwa
from $1,901 
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Kona Koa House by Gather: Oceanview 3BR Estate w/ Pool, Spa & BBQ
Kona Koa House by Gather: Oceanview 3BR Estate w/ Pool, Spa & BBQ
Kona Koa House by Gather: Oceanview 3BR Estate w/ Pool, Spa & BBQ

Kona Koa House by Gather: Oceanview 3BR Estate w/ Pool, Spa & BBQ

Luxury Oceanview 4-Bedroom Vacation Rental with Infinity Pool – Kona Koa House by Gather.

Escape to Kona Koa House by Gather, a premier four-bedroom, three-bathroom luxury vacation rental in the exclusive Keauhou Estates, a 24-hour guard-gated community in Kailua-Kona, Hawaiʻi.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $1,109 
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Honuala Estate, a Majestic Ocean Front Residence
Honuala Estate, a Majestic Ocean Front Residence
Honuala Estate, a Majestic Ocean Front Residence

Honuala Estate, a Majestic Ocean Front Residence

16 acres with approx. 450 lineal feet of prime ocean frontage on the Kohala Coast. Located in a resort zone and near several world class beaches on the Big Island of Hawaii. Every fine detail of this property is sophisticated, timeless, and epitomizes Hawaiian style with six bedrooms, seven full and one half baths as well as an office, expanded 2 two car enclosed garages, covered lanai's and private patios of over 11,000 square feet.

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Waimea
from $4,589 
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Luxury Dolphin Bay Estate on Big Island Hawaii
Luxury Dolphin Bay Estate on Big Island Hawaii
Luxury Dolphin Bay Estate on Big Island Hawaii

Luxury Dolphin Bay Estate on Big Island Hawaii

Dolphin Bay Estate offers an enchanting escape on the pristine shores of Big Island, Hawaii. This luxurious property combines serenity, elegance, and convenience, making it the perfect Hawaiian retreat.
Nestled in the charming town of Captain Cook, the estate is just a two-minute walk from a secluded private beach, providing guests with privacy and tranquility while remaining close to the island's top attractions.

  • 5 bedroom
  • 5 bathroom
  • Sleeps 13
Hawaii> Captain Cook
from $982 
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Luxury Aloha Escape Turtle Bay - Kuilima Estates West
Luxury Aloha Escape Turtle Bay - Kuilima Estates West
Luxury Aloha Escape Turtle Bay - Kuilima Estates West

Luxury Aloha Escape Turtle Bay - Kuilima Estates West

Discover this inviting 2-bedroom condo in Kahuku, ideal for a relaxing Hawaii vacation. The property features a comfortable king bed and twin bed, perfect for families or couples. Modern amenities like high-speed WiFi, air conditioning, and a washing machine ensure a convenient stay.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $1,180 
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Hale 'Ae Kai – Balinese-Inspired Oceanfront Estate
Hale 'Ae Kai – Balinese-Inspired Oceanfront Estate
Hale 'Ae Kai – Balinese-Inspired Oceanfront Estate

Hale 'Ae Kai – Balinese-Inspired Oceanfront Estate

Experience the ultimate luxury retreat at Hale 'Ae Kai, a world-class Balinese-inspired estate set on 15 acres overlooking the famous Secret Beach. This exquisite property features four interconnected buildings surrounded by lush gardens and serene ponds, offering privacy and tranquility.

  • 4 bedroom
  • 7 bathroom
  • Sleeps 8
Hawaii> Kilauea
from $21,467 
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Luxury Hualalai Estate Villa with Ocean Views
Luxury Hualalai Estate Villa with Ocean Views
Luxury Hualalai Estate Villa with Ocean Views

Luxury Hualalai Estate Villa with Ocean Views

5-bathroom fully renovated estate villa offers a luxurious and spacious retreat. With high-end finishes, museum-quality art, and a flexible floor plan, it provides the ultimate resort experience for up to 8 guests. The main residence features a generous primary suite and two guest suites, each equipped with modern comforts and flat-screen TVs.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $7,618 
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Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East
Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East
Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East

Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East

Welcome to this charming 1-bedroom condo nestled within a peaceful community, blending comfort and recreation seamlessly. The spacious bedroom features a luxurious king-size bed, complemented by a pull-out couch, comfortably accommodating up to four guests.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $501 
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Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Lanikai Hillside Estate – Panoramic Luxury Above the Sea

Lanikai Hillside Estate – Panoramic Luxury Above the Sea

This exquisite property offers a luxurious escape on the remote islands of Lanikai, blending modern elegance with natural beauty. Spanning over 8,400 square feet, this estate features seven spacious bedrooms, each designed for comfort and style, with the primary suite offering panoramic ocean views, a walk-in closet, and a chic Agape bathroom.

  • 7 bedroom
  • 7 bathroom
  • Sleeps 10
Hawaii> Kailua
from $4,165 
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Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views

Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views

The Hualalai Resort will host an exclusive private event from December 1–6, 2025. Please note that access to certain resort amenities may be limited or restricted during this time for residential rental guests. We recommend inquiring prior to booking if your stay falls within these dates.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $3,732 
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Hale Moana Estate - Beach front, Lg yard
Hale Moana Estate - Beach front, Lg yard
Hale Moana Estate - Beach front, Lg yard

Hale Moana Estate - Beach front, Lg yard

Welcome to the perfect stay for large groups looking for a beach home! We have room to fit your whole family! This is the perfect paradise getaway for those seeking a calm, private, and relaxing Hawaiian vacation. The sand and water are just steps away.

  • 10 bedroom
  • 6 bathroom
  • Sleeps 34
Hawaii> Laie
from $2,668 
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Noiulu One – Brand New Hualalai Estate
Noiulu One – Brand New Hualalai Estate
Noiulu One – Brand New Hualalai Estate

Noiulu One – Brand New Hualalai Estate

5-bathroom gated estate offers a luxurious coastal retreat with breathtaking ocean vistas. Spanning 6,400 sq ft, the home features a seamless blend of modern design and natural finishes, creating an elegant yet inviting atmosphere for up to 12 guests.

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Kailua Kona
from $10,080 
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Puka Pa 4 – Hualalai Luxury Estate
Puka Pa 4 – Hualalai Luxury Estate
Puka Pa 4 – Hualalai Luxury Estate

Puka Pa 4 – Hualalai Luxury Estate

This stunning estate located in the exclusive Puka Pa neighborhood is just a short 6-minute drive from the vibrant heart of Hualalai. Spread across nearly 5,000 sq ft, this residence offers five spacious bedroom suites that comfortably accommodate up to 10 guests in bright, contemporary luxury.

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua Kona
from $8,762 
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Laueki 8 – 4BR Hualalai Luxury Estate
Laueki 8 – 4BR Hualalai Luxury Estate
Laueki 8 – 4BR Hualalai Luxury Estate

Laueki 8 – 4BR Hualalai Luxury Estate

Experience the pinnacle of luxury living at Hualalai Resort with this stunning private residence. 5-bath home offers breathtaking panoramic ocean views and exceptional amenities for a memorable stay.
The property is thoughtfully designed with island-inspired decor, featuring an expansive outdoor lanai with pocket doors that open to the ocean and an oversized heated infinity-edge pool with a wet deck and hot tub—perfect for relaxing or entertaining guests.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $7,559 
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Luxury 6BR Hale o ka Nene Estate w/ Pool/Spa & Golf Views, Near Beach
Luxury 6BR Hale o ka Nene Estate w/ Pool/Spa & Golf Views, Near Beach
Luxury 6BR Hale o ka Nene Estate w/ Pool/Spa & Golf Views, Near Beach

Luxury 6BR Hale o ka Nene Estate w/ Pool/Spa & Golf Views, Near Beach

Welcome to Hale o ka Nene by Gather, a luxurious six-bedroom, six-and-a-half-bathroom estate on the sunny South Shore of Kaua'i. Perfect for families or group getaways, this private retreat accommodates up to 15 guests and features panoramic golf course views, a private pool and spa, and seamless indoor-outdoor living.

  • 6 bedroom
  • 7 bathroom
  • Sleeps 15
Hawaii> Koloa
from $3,655 
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Beautiful Bayside Estate with Ocean Views and Private Yard
Beautiful Bayside Estate with Ocean Views and Private Yard
Beautiful Bayside Estate with Ocean Views and Private Yard

Beautiful Bayside Estate with Ocean Views and Private Yard

Bayside Estate offers stunning ocean vistas that truly impress. Large windows bring the picturesque scenery inside, perfect for relaxing with a book or enjoying your favorite shows on the smart TV. The spacious kitchen is fully equipped, making meal prep a breeze for the chef in your group.

  • 6 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Kaneohe
from $2,430 
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Ohana House: Authentic Hawaiian Family Retreat
Ohana House: Authentic Hawaiian Family Retreat
Ohana House: Authentic Hawaiian Family Retreat

Ohana House: Authentic Hawaiian Family Retreat

The Ohana House, established by the Lenett family in 1998, offers a unique Hawaiian experience on Big Island. Designed with influences from Balinese, Japanese, and native Hawaiian architecture, this home provides a truly authentic and luxurious retreat.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kailua-Kona
from $669 
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Luxury Kauai Vacation Home in Poipu Beach Estates
Luxury Kauai Vacation Home in Poipu Beach Estates
Luxury Kauai Vacation Home in Poipu Beach Estates

Luxury Kauai Vacation Home in Poipu Beach Estates

Experience the ultimate Kauai escape in this stunning new luxury home nestled in the prestigious Poipu Beach Estates. Ideally located between The Shops at Kukui'ula and Poipu Shopping Village, and just a five-minute drive to the renowned Poipu Beach, this residence combines convenience, comfort, and island elegance.

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Koloa
from $1,261 
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Luxury Estate at Hualalai Resort- Sweeping Ocean and Golf Course Views ** 2 Golf Carts**
Luxury Estate at Hualalai Resort- Sweeping Ocean and Golf Course Views ** 2 Golf Carts**
Luxury Estate at Hualalai Resort- Sweeping Ocean and Golf Course Views ** 2 Golf Carts**

Luxury Estate at Hualalai Resort- Sweeping Ocean and Golf Course Views ** 2 Golf Carts**

A Sanctuary of Luxury – Lau‘eki Estates at Hualalai Resort

Discover refined Hawaiian living at its finest in this exceptional estate, nestled within the exclusive Lau‘eki Estates at the world-renowned Hualalai Resort.

A perfect harmony of tranquility, sophistication, and adventure awaits—set against a backdrop of lush tropical landscapes and panoramic views of the Pacific Ocean.

  • 5 bedroom
  • 7 bathroom
  • Sleeps 10
Hawaii> Kailua Kona
from $7,744 
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NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC

NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC

Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to offer. With luxury and elegance from the moment you pull into the driveway, Hale Waipo’o is sure to be your luxury home away from home.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Koloa
from $1,385 
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