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Kailua Kona Luxury Vacation Rentals

Start Your Vacation Rental Search > Hawai’i Vacation Rentals and Villas > Big Island Luxury Vacation Rentals > Kailua Kona Luxury Vacation Rentals

Browse Gather’s collection of Kailua Kona luxury vacation rentals, offering unparalleled ocean views and easy access to white sand beaches, surfing, snorkeling, and incredible food and culture. Gather’s vacation rentals on the Kona coast feature a wide variety of price points and sizes, all with the exceptional quality and services you can trust. Enter in dates and desired amenities, bedroom count, and more to find the perfect luxury rental in Kailua Kona.

Popular Big Island Destinations

Hilo/Hamakua Coast | Hualalai | Kailua Kona | Keauhou | Mauna Kea | Mauna Lani | Puako | Waikoloa
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The average night price is $2,019

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    Enjoy seamless flow from the living, kitchen and dining areas. The living room offers a comfortable space with ample seating and a large TV, perfect for unwinding with loved ones. Enjoy your morning coffee on the lanai with golf views! Al fresco dining on the lanai with table for six. Lounge in the living area with comfy sofas and TV. Indulge your culinary expertise in the kitchen area with top-tier appliances, plenty of storage and counter spaces. The kitchen bar has seating for three, perfect for quick meals and entertainment.

New Listing!

3BD Ka'ulu Villa (129B) at Four Seasons Resort at Hualalai

3 Beds
3 Baths
6 Sleeps

Starting at $903/night

    Revel in the Lihikai Master Suite: Your private haven with sweeping ocean vistas from the lanai. Experience grandeur in the Lihikai Master Suite, boasting a plush king bed, state-of-the-art TV, and a luxurious spa-inspired ensuite. Indulge in relaxation in the Lihikai Master ensuite soaking tub, as expansive windows frame breathtaking ocean views Experience tranquility in the spacious spa-like ensuite, featuring a walk-in shower and thoughtful privacy blinds on expansive windows framing ocean vistas Unwind in the serene ambiance of the Lihikai lounge area. Step into the expansive Lihikai Master Suite, where luxury meets tranquility. Experience the grandeur of the Moana Hale Great Room, where every moment becomes a cherished memory.

Kona Beach Bungalows**

12 Beds
9 Baths
24 Sleeps

Starting at $6,000/night

    Exquisite newly remodeled and redesigned estate home with private pool & spa at twilight. The majestic Hawaiian sunset from this exquisite estate's private spa. Ample pool deck lounge seating and multiple lanais (decks). Views of the sunset, golf course and the deep blue Pacific Ocean beyond. Lounge in paradise in the private spa with a waterfall feature into the stone set infinity pool. Detail of the view with iconic trees and ocean. Exterior entrance with private parking area & key-code exterior entrance doors.
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4BD Pakui Street (147) Estate Home at Four Seasons Resort at Hualalai

4 Beds
4 Baths
8 Sleeps

Starting at $2,186/night

    Gorgeous new construction luxury estate home professionally designed by Gina Willman Interiors with infinity pool, private spa and ocean views. Contemporary design elements delight the senses, like this overflow waterfall from private spa to infinity pool. Open floor plan great room steps out to lanai, barbecue area, pool and spa through floor to ceiling pocket doors. The living area’s wraparound plush seating, inset entertainment wall with 75” smart flat screen TV and Sonos audio system provide entertainment perfection. Aerial view showcasing premiere location, private yard and expansive lanai. Vaulted ceilings with mahogany trim and cove lighting and an elegant formal dining table for eight. Reverse view of great room highlighting sliding glass pocket doors in front entryway.

4BD Kulanakauhale (3558) Estate Home at Four Seasons Resort at Hualalai

4 Beds
4.5 Baths
8 Sleeps

Starting at $2,500/night

    Paradise awaits at the 102 Hainoa Estate Back of this stunning estate with an astonishing view of Hualalai Looking back to the lanai & private yard from the pool An oasis of tranquility Sit back, relax, & soak in the views of the vividly blue Pacific past the infinity pool Elegant front entrance with vibrant landscaping The foyer invites you into stunning architecture & serene interior design
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4BD Hainoa Estate (102) at Four Seasons Resort at Hualalai

4 Beds
4.5 Baths
8 Sleeps

Starting at $1,890/night

    Your private escape at the luxury Puka Pa Estate 1201 with infinity pool and expansive outdoor living. Indulge in ultimate relaxation as you enjoy breathtaking views. Large pool with spa, a lush private lawn and an inviting outdoor living spaces for the perfect vacation. Luxury awaits: serene light, cozy lounger, sky and lava in harmony. Golf course and Pacific views views from the pool. Soaring ceilings in the great room that opens to the expansive lanai. Seamless open-concept floor plan blends the comfortable living spaces.
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4BR Luxury Puka Pa Estate (1201) at Four Seasons Resort at Hualalai

4 Beds
4.5 Baths
8 Sleeps

Starting at $2,119/night

    Pakui 131 Estate Home - Where luxury meets serenity Infinity pool toward the ocean & vast blue sky Front entrance guided by lush & tropical surroundings Elegant foyer with a gorgeous entryway bench Plush seating & beautiful views welcome you The living room offers a retreat for relaxation with floor to ceiling pocket doors to the lanai Gaze at tranquil views while lounging on the lanai
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3BD Pakui Street (131) Estate Home at Hualalai Resort

3 Beds
3.5 Baths
6 Sleeps

Starting at $1,923/night

    Luxury meets serenity, the view from your private pool in paradise. One of a kind property for your best vacation yet! Angle in on the private spa, pool, and covered lanais. Stylish and modern al fresco dining with ocean views, BBQ grill. Living area with vaulted ceilings and bold beautiful fabrics and colors. Spacious open concept kitchen with center island and bar seating. Use of two 4-Seater golf carts is included with your rental.
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4BD Hainoa Estate (122) at Four Seasons Resort at Hualalai

4 Beds
4.5 Baths
8 Sleeps

Starting at $1,995/night

    No better place to be to take in the tranquil lifestyle Hawai'i has to offer! No better place to be to take in the tranquil lifestyle Hawai'i has to offer! Ocean infinty pools and coco palms remind you why you came to paradise Gorgeous sunset dining experiences Lounge the day away with a relaxing view! Lounge the day away! Whether you plan to exercise or lounge around this is the place to be!
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Ali'i Point #9

3 Beds
3.5 Baths
6 Sleeps

Starting at $2,000/night

    Unwind, stretch out & soak in the stunning ocean views Spacious backyard with private pool, spa, covered daybed & luscious lawn Embrace extraordinary views from your private oasis in paradise Stylish lanai lounge space, al fresco dining for 8 with ocean views & a nearby grilling station The elegant great room opens to the lanai, offering expansive views & an indoor/outdoor living experience Spacious modern kitchen with gleaming quartzite countertops, capiz shell backsplash & a circular, open flow Indoor dining area for 6 with a view of the exterior courtyard & pond features
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4BD Kahikole Street (218) Estate Home at Four Seasons Resort at Hualalai

4 Beds
4.5 Baths
8 Sleeps

Starting at $1,995/night

    Luxurious estate living with a hot tub and spacious lanai area at Kailua Kona Estate. A welcoming and airy living space with vaulted ceilings and wall-to-wall windows, offering unobstructed ocean views for a serene living experience. Spacious living area with a stone fireplace to gather with your loved ones. Alternative view of the living room with sky lights. Prepare your favorite drink at the living room wetbar for an sunset toast. Enjoy expansive ocean views from the loft and balcony. Enter into the spacious kitchen with plenty of seating for everyone in your group.

Kailua Kona Estate**

6 Beds
6 Baths
16 Sleeps

Starting at $2,645/night

    Primary lanai w/ocean view & tropical foliage. Map to demonstrate the proximity of your villa rental to resort center. Private hot tub on generous lanai w/ front row ocean & golf course views. Wide view of your private lanai - ground floor golf villas are perfect for children to run and play right outside the home. Closer view of lanai loungers with ocean views. Elegant breakfast table with ocean views. View looking from from in front of the villa towards the green of the 18th, the resort pro shop and one of the resort restaurants.

Hot Tub

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3BD Golf Villa (3101) at Four Seasons Resort at Hualalai

3 Beds
3.5 Baths
6 Sleeps

Starting at $1,073/night

    Spectacular location to watch the sun dip past the horizon. The picture perfect space for entertaining with views of the stars and sunset The stylish great room offers expansive colorful views Ample plush seating to soak in the views of Maui Back of this stunning villa showcasing the upper and lower lanais Gourmet kitchen with top tier appliances and bar seating Stunning great room with chic decor and vaulted ceilings
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3BD Hali'ipua Villa (120) at Four Seasons Resort at Hualalai

3 Beds
3 Baths
6 Sleeps

Starting at $900/night

    A back drop out of a magazine at Hale Pua! Watch the waves roll in as your troubles melt away Living room seating and Smart TV Outdoor dining for 8 guests pool side Access from the living room to the yard and pool area Peaceful reading nook below the stairs to the Primary bedroom Breathtaking art work throughout
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Hale Pua

5 Beds
6 Baths
16 Sleeps

Starting at $1,200/night

    Ocean view al fresco dining in paradise Beautiful landscaping, golf course and ocean views from the lanai. Ocean view great room of this elegant and newly redecorated property View from lanai into the great room featuring an elegant formal dining set for six. Brand new granite countertops and top tier appliances in the modern kitchen. Downstairs primary bedroom suite with private deck, flat screen TV, sliding doors to bonus retreat room, and en-suite bath. Beautifully redesigned primary bedroom with Zen-style bed, private deck, flat screen TV, walk-in closet and en-suite bath.

3BD Ka'Ulu Villa (131C) at Four Seasons Resort at Hualalai

3 Beds
3 Baths
6 Sleeps

Starting at $955/night

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