Kaupulehu Luxury Vacation Rentals on the Big Island
Kaupulehu is an ultra-luxury destination on the Big Island's Kona-Kohala Coast, home to upscale oceanfront villas, private estates, and the renowned Four Seasons Resort Hualalai. Surrounded by lava rock landscapes and pristine beaches, this area offers five-star amenities, championship golf, fine dining, and privacy for elite travelers. Our Kaupulehu vacation rentals provide the perfect base for an unforgettable Hawaiian escape in one of the island's most exclusive enclaves.
Discover the Luxurious Kaupulehu Experience
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.
Top Features of Kaupulehu Vacation Rentals
- Private, oceanfront villas and estates
- Proximity to the Five-Star Four Seasons Resort Hualalai
- Exclusive access to championship golf courses and luxury amenities
- Stunning views of the Kona-Kohala Coast, perfect for relaxation or adventure
- Full-service spas, fine dining, and other five-star experiences nearby
Why Stay in Kaupulehu
- Experience world-class luxury and privacy
- Unbeatable beachfront access and breathtaking ocean views
- Stay in the heart of one of the most exclusive areas on the Big Island
- Indulge in top-tier amenities and services designed for ultimate relaxation
Nearby Attractions & Activities
- Golf at the renowned Hualalai Resort and other championship courses
- Explore the stunning beaches and lava rock landscapes of the Kona-Kohala Coast
- Relax at the Five-Star Four Seasons Resort Hualalai
- Enjoy world-class dining, luxury spas, and shopping experiences in the area
Nearby Upscale Rentals
For additional upscale rental options nearby, explore our Hualalai vacation rentals, just minutes away and equally rich in luxury and charm.
3BD Ka'ulu Villa (129B) at Hualalai Resort
Important Resort Notices• Each December, Hualalai Resort holds its annual Chairman’s Club event. This event will result in temporary modifications to guest access at select resort amenities. Access is managed entirely by Hualalai Resort and may change at their...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
Important Resort Notices* Each December, Hualalai Resort holds its annual Chairman’s Club event. This event will result in temporary modifications to guest access at select resort amenities. Access is managed entirely by Hualalai Resort and may change at their...
Kahikole Villa: Hualalai Resort Remodeled Villa with Pool & Spa
*Newly Remodeled*Kahikole 4 bedroom Luxury Villa on the 8th fairway of the Nicklaus designed Hualalai Golf Course. Incredible views over the 8th and 4th greens, ocean views and sunsets.Kahikole Villa offers 3 bedrooms in the main living area with two outdoor shower...
Hualalai Resort: Ground Level Villa by the Ocean
Hillside 1102 is nestled near the shore in the exclusive 5 Star Four Seasons Hualalai Resort. From the lanai, listen to the rhythmic waves on the shore, just a short walk from the Villa. Fully receding pocket glass, screen and shutter doors capture warm ocean breezes...
Stunning Ocean Views - Hualalai Resort- 18th Fairway - Prime Location - Golf Cart Included
Magnificent Garden Level Villa located on the #18 hole of the Hualalai Jack Nicklaus Signature Course. Enjoy white water views and spectacular sunsets from this highly desirable location at Hualalai Resort. Listen to the ocean and whale watch during the winter months...
Private 3BR Hualalai Villa with Pool & Spa
This beautiful and meticulously maintained home situated on the 9th hole of Hualalai's Jack Nicklaus golf course with Pacific Ocean views is available for private rentals. Perfectly located, the home is just a short walk or golf cart ride (two golf carts provided) to...
Ocean Views! Excellent Proximity to Hualalai Resort Amenities! Includes Golf Cart
Located in the Award Winning Resort Community of Hualalai Four Seasons.Beautiful ocean views from this delightful two bedroom Garden Level Villa. Spacious Lanai with lounge seating extends seamlessly to a large lawn area. Enjoy the sounds of the ocean and glances of the...
Panoramic Ocean and Golf Course Views ! Luxury Multi Level Townhouse at Hualalai Resort- includes 2 Golf Carts
Ke Alaula Villa 217B at Hualalai ResortExperience unparalleled luxury and tranquility at Ke Alaula Villa 217B, located within the prestigious Hualalai Resort. This exceptional property is situated within one of Hawaii’s most renowned and award-winning resorts,...
Gorgeous Luxury Estate Home - Hualalai Resort - Spectacular Ocean and Golf Course Views - Private Pool and Spa - 3 Golf Carts Included
Gorgeous, Contemporary, Newer Home Exemplifies Luxury and ease of Living in our Island Paradise. This 5-bedroom, 5 1/2 bath pod-style estate home is exceptionally appointed and designed to take full advantage of the temperate climate and island breezes.Upon arrival to...
OCEAN VIEWS* LUXURY AND LOCATION AT HUALALAI RESORT ** TWO GOLF CARTS**
Located in the Award Winning Resort Community of Hualalai Four Seasons.Enjoy the sounds of the ocean serenade, the magic of sunsets, and whale watching during the winter months, from this recently updated garden level Hillside Villa. Appreciate the close proximity to...
Premier Luxury 3 bedroom Villa at Hualalai Resort with Golf Course Views!
Turn moments into memories at this private villa located inside the gated community of the iconic Four Seasons at Hualalai Resort. Experience world-class golf, spa, restaurants, and more. Waiulu Villa, 133C is a three-bedroom, 3-and-a-half-bathroom luxury ground floor...
Lau'eki Estate at Hualalai Resort - Sweeping Ocean and Golf Course Views ** 2 Golf Carts**
A Sanctuary of Luxury – Lau‘eki Estates at Hualalai ResortDiscover 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...
Waiulu Villa at Hualalai Resort: Modern 3BR Villa w/ Lanai, Golf Carts & Pool Ac
Important Resort Notices• Each December, Hualalai Resort holds its annual Chairman’s Club event. This event will result in temporary modifications to guest access at select resort amenities. Access is managed entirely by Hualalai Resort and may change at their...
Pohinahina Hale – 5BR Retreat at Hualalai Resort
Located just 6 minutes to the heart of the resort, Pohinahina Hale offers a spacious and secluded retreat for up to 10 guests. Two primary suites and two bedrooms are located in the main home, plus another bedroom located in a separate ohana (guest house). This home...
Cozy Villa that near to Hualalai Resort Beach!
This centrally located three bedroom, three and a half bathroom luxury villa overlooks the 15th hole of the majestic Jack Nicklaus-designed Hualalai Golf Course. The ground floor single level floor plan has a spacious lanai that extends to private lawn area - great...