Kaupulehu Luxury Vacation Rentals on the Big Island

Kaupulehu, located along the prestigious Kona-Kohala Coast, is one of the Big Island’s most exclusive destinations. This upscale community is known for its luxurious oceanfront estates, dramatic lava rock landscapes, and world-class amenities. It is also home to the acclaimed Four Seasons Resort Hualalai, a five-star property offering fine dining, spa experiences, golf, and impeccable beachfront service-making it a magnet for luxury travelers.

We features a prime collection of vacation rentals in Kaupulehu, including elegant villas and expansive private homes that offer the ultimate in privacy and comfort. Whether you're here to relax poolside, enjoy a round of golf, or simply take in the serene coastal views, Kaupulehu delivers a refined Hawaiian experience.

For additional upscale rental options nearby, explore our Hualalai vacation rentals, just minutes away and equally rich in luxury and charm.

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Hualalai Four Seasons Garden Level Villa with Ocean Views

Located within the prestigious Hualalai Four Seasons Resort Community, this recently renovated garden level Hillside Villa offers an idyllic Hawaiian escape. Wake to the soothing sounds of the ocean, witness breathtaking sunsets, and partake in whale watching during the winter months, all from the comfort of your villa.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kailua-Kona

from $2,153 

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Luxury Hillside 1102 Villa at Four Seasons Hualalai

Hillside 1102 is a luxurious ground-floor villa nestled within the exclusive Four Seasons Hualalai Resort, offering breathtaking ocean views and direct access to a pristine white sand beach. The villa's contemporary design features fully retractable pocket glass, screen, and shutter doors that bring the warm ocean breezes indoors, creating a seamless blend of indoor comfort and outdoor beauty.

• 2 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Kailua-Kona

from $1,836 

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Luxury Kahikole Villa on Hualalai Golf Course

*Newly Remodeled* Kahikole 4-bedroom luxury villa situated on the 8th fairway of the Nicklaus-designed Hualalai Golf Course. Panoramic views over the 8th and 4th greens, ocean vistas, and breathtaking sunsets create an unparalleled setting for your vacation.

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Kailua Kona

from $3,726 

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Luxury Garden Level Golf Villa at Hualalai Resort

Experience the luxury of Garden Level Golf Villa 1101 at Hualalai Resort, offering breathtaking views of the golf course and ocean from a highly desirable corner location. The spacious lanai provides an ideal spot to unwind, watch the sunrise or sunset, and enjoy tropical breezes.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $1,958 

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Luxury Hualalai Golf Villa with Ocean Views

Experience the ultimate luxury at this magnificent garden-level villa located on the #18 hole of the prestigious Hualalai Jack Nicklaus Signature Course. The property boasts spectacular white water views and mesmerizing sunsets from its prime location within Hualalai Resort.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua-Kona

from $2,806 

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Luxury Ke Alaula Villa 217B at Hualalai

Experience unparalleled luxury and serenity at Ke Alaula Villa 217B within the prestigious Hualalai Resort. This exquisite 3-bedroom, 3-bathroom villa offers 2,657 sq ft of elegant living space, complemented by a spacious 940 sq ft lanai that provides breathtaking views of the ocean, lush golf course, and surrounding mountains.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua-Kona

from $2,090 

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Luxury Hualalai Estate with Ocean Views and Pool

5-bath estate at Hualalai Resort into a contemporary, opulent retreat that embodies island elegance. Spanning over 3,500 square feet of interior living space, this home offers a seamless blend of luxury, technology, and comfort.
The open-concept great room features expansive sliding glass pocket doors that open to a spacious lanai, pool deck, and lush grassy lawn, creating an ideal setting for indoor-outdoor living.

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Kailua Kona

from $3,735 

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Spectacular Hawaiian Estate with Ocean Views and Luxe Amenities

Pursue your dream vacation in this picturesque Hawaiian estate located on the stunning Kohala Coast. The property boasts multiple bedroom suites with outdoor garden showers, offering a perfect blend of luxury and natural beauty. The residence features an impressive indoor and outdoor chef's kitchen, ideal for gourmet cooking and entertaining while enjoying breathtaking ocean views from the expansive lanai.

• 4 bedroom
• 5 bathroom
• Sleeps 10

Hawaii> Kailua-Kona

from $5,987 

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Luxury Ocean View Villa at Hualalai Four Seasons

Experience the ultimate Hawaiian escape in this beautiful two-bedroom garden-level villa located within the prestigious Hualalai Four Seasons Resort Community. From the spacious lanai with lounge seating, enjoy uninterrupted ocean views and the soothing sounds of the shoreline, all from this hillside setting.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Kailua-Kona

from $1,744 

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Luxury Hualalai Golf Course Villa with Ocean Views

This stunning and carefully maintained home is located on the 9th hole of Hualalai's renowned Jack Nicklaus golf course, offering breathtaking views of the Pacific Ocean. Situated in an ideal location, the property is just a short walk or golf cart ride (with two golf carts provided) to the luxurious amenities of the Four Seasons Hualalai Resort, including golf, tennis, spa, pools, dining, and water activities.

• 3 bedroom
• 1 bathroom
• Sleeps 6

Hawaii> Kailua-Kona

from $3,874 

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Luxury Hualalai Island Resort Home with Golf Views

Experience the epitome of luxury in this contemporary, newly built estate located within Hualalai Resort on the Big Island of Hawaii. 5-bath pod-style home seamlessly blends indoor and outdoor living, capturing the island’s temperate climate and refreshing breezes.

• 5 bedroom
• 5 bathroom
• Sleeps 10

Hawaii> Kailua Kona

from $6,555 

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Luxury Waiulu Villa at Four Seasons Hualalai

Experience a luxurious escape at Waiulu Villa, nestled within the prestigious Four Seasons at Hualalai Resort. This spacious ground-floor three-bedroom home offers a perfect blend of comfort, privacy, and access to world-class amenities.
Upon entering through a private courtyard, you are greeted by a generous entryway that sets the tone for this elegant residence.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $1,438 

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Luxury Waiulu Street Villa at Hualalai Resort

Discover a beautifully redesigned 3-bedroom villa on Waiulu Street at Hualalai Resort, offering a perfect blend of elegance and comfort. This newly renovated retreat features contemporary interior design, high-end furnishings, and custom artwork, creating an inviting atmosphere for up to 6 guests.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $1,822 

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Luxury 3BR Ka'ulu Villa at Hualalai Resort

Welcome to 3BD Ka'ulu Villa (129B) at Hualalai Resort, a private and luxurious three-bedroom, three-bath townhome situated in Kailua Kona, HI. Overlooking the Nicklaus #4 fairway, this villa offers breathtaking views of the ocean and Maui beyond, providing an idyllic setting for a relaxing Hawaiian getaway.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $1,476 

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Luxury Hillside Villas with Ocean Views in Hawaii

Welcome to Hillside Villas, your tranquil sanctuary nestled in the heart of paradise. These beautifully appointed villas offer the perfect blend of luxury and comfort, with spacious open-concept living areas designed for relaxation and entertaining.

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Kailua Kona

from $6,657 

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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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Pohinahina Hale – 5BR Retreat at Hualalai Resort

Pohinahina Hale offers a spacious, private retreat just 6 minutes from the heart of Hualalai Resort, accommodating up to 10 guests in style and comfort. This 5,740 sq ft luxury estate features two primary suites, two additional bedrooms in the main home, and a separate ohana (guest house), providing ample space for family and friends.

• 5 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Kailua Kona

from $8,723 

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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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