Kaupulehu Vacation Rentals

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. ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $2,125 
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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 ...

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $6,395 
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Panoramic Ocean and Golf Course Views ! Luxury Multi Level Townhouse at Hualalai Resort- includes 2 Golf Carts

Ke Alaula Villa 217B is located in the Award Winning Resort Community of Hualalai Four Seasons.

3 Bedrooms / 3 Baths
Living Area: 2,657 sqft and 940 sqft of Lanai
Ocean,Golf Course and Mountain Views
Spilt Level Townhouse
2 ~...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $2,119 
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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 ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua-Kona
from $1,734 
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Private home at Hualalai Resort, near Four Seasons. Pool, Spa, Exclusive!

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 ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $4,105 
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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 ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $2,783 
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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 ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua-Kona
from $1,836 
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Hualalai Resort Remodeled Villa w/ Pool, Spa & Views

*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 ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $3,798 
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Designer Oceanview Estate w/Pool & Spa, at Hualalai Resort: 122 Hainoa

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $5,167 
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Prime Location, Luxury Villa at Hualalai Resort: 120C Fairways

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kailua Kona
from $1,643 
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Makai Estate by Cuvee | Hualalai Resort 4 BR EXCLUSIVE OFFER Private Chef Incl.

WHY IT'S SPECIAL

Picturesque, bedroom island suites with outdoor garden showers, premiere resort location, impressive indoor and outdoor chef's kitchen, and oceanside views from the sprawling lanai.

Completely relish in the ...

  • 4 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $5,379 
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Magnificent Golf Course and Ocean Views -Hualalai Resort -18th Green- Golf Cart included

Magnificent Garden Level Golf Villa 1101 enjoys golf course and water views from this highly desirable location at Hualalai Resort.

From sunrise to sunset unwind on the spacious lanai- gazing at the verdant green golf course, with the ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $2,440 
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Beautiful Ocean View Villa at Hualalai Resort w/ AC and Lanai

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $2,070 
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Luxury 4BR Puako Estate, Hualalai Resort: Golf Carts, Pool & Ocean View

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $4,039 
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3BR Ka'Ulu Villa 109A at Hualalai Resort Hualalai w/ Ocean Views & Resort Amenit

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,817 
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Luxury Designer Estate at Hualalai Resort - Private Pool & Spa: 147 Pakui

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $3,324 
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Premier Villa at Hualalai Resort

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 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,577 
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Luxury 3-Bedroom Oceanfront Villa in Kailua-Kona - Hualālai Resort

Welcome to Hillside Villas, your serene escape nestled in the heart of paradise. Experience the perfect blend of luxury and tranquility in our beautifully appointed villas, where breathtaking views and world-class amenities await. Whether you're...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $4,676 
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217C Ke Alaula Villa: Luxurious 3BR Townhome in Hualalai Resort w/ Lanais

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,886 
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3BD Ka'ulu Villa (129B) at Hualalai Resort

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,528 
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Waiulu Villa at Hualalai Resort: Modern 3BR Villa w/ Lanai, Golf Carts & Pool Ac

The Annual Chairman's Club Event at Hualalai Resort will take place from Monday December 01 through Saturday December 06, 2025. This event will result in modified access to select resort amenities.

The annual Mitsubishi Electric ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,511 
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