Luxury Vacation Rentals in Hawaii

Explore the most exclusive Hawaii luxury vacation rentals with our handpicked portfolio of Oahu beachfront estates, Maui private villas, Kauai oceanview homes, and Big Island luxury retreats. These high-end vacation homes feature private pools, chef kitchens, panoramic views, and resort-style amenities – ideal for honeymoons, family reunions, and indulgent island escapes.

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Luxury Estate with Panoramic Honolulu views. Steam room, Sauna, Spa, Heated Pool

The ultimate contemporary estate to de-stress, unwind and recharge your well-being. Luxury hotel and spa experience without the crowd and traffic. It can accommodate multiple families and corporate retreats, providing private and shared spaces, allowing guests to come...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Honolulu, Hawaii

Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub

"Out of all our experiences with hosts on AirBnb, Kaili's was by far our most memorable. Not only is this house an amazing home for large families or groups to enjoy, but it's so centrally located to most top beaches, grocery and shopping on the Kona side of the...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 16
📍 Kailua-Kona, Hawaii

Plantation House by Destination Kauai - Poipu Beach Estates, Central A/C, 3BD

E Komo Mai, Welcome to “Plantation House In Poipu Beach Estates”Luxury Hawaiian living at its best! Enjoy cooking in a fully equipped gourmet kitchen with an open dining and living floor plan. This new and modern vacation home is uniquely decorated with style,...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Koloa, Hawaii

Beach Glam @ Turtle Bay - Kuilima Estates West

We are all looking for a quiet, restful, safe place to de-stress and forget the troubles of the world. As a Hawaii born and raised local, there are few places that can rival this task than the North Shore on Oahu. With 24 hr security, free parking, and the Turtle Bay...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kahuku, Hawaii

Probably The Most Peaceful & Beautiful of North Shore Estate

Greetings! Welcome to the - HaleAlohaEstate - on Oahu's North Shore. Come experience a truly authentic Hawaiian experience in our beautiful Estate home with 6+ bedrooms, and 4.5 bathrooms on the quiet – best part of Oahu’s famous North Shore. Enjoy the 5-acres...

🛏 6 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 20
📍 Waialua, Hawaii

Luxury Coffee Estate - Infinity Pool - Endless Views

*Our minimum stay is 2 nights. Our pricing reflects this access to a truly wonderful estate and the amenities outlined below. Please note that from 2023 our rate nightly rate will be based on an occupancy of 4 persons.The Vista Suite is located on the South side of the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 5
📍 Holualoa, Hawaii

Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai

The Hualalai Resort will host the annual Chairman’s Club 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...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua Kona, Hawaii

Ocean Pearl at Turtle Bay Resort - Kuilima Estates West

Ocean Pearl is a luxurious retreat nestled in the heart of scenic Turtle Bay Resort, offering a perfect blend of comfort, convenience, and breathtaking views. With three full bedrooms and two full Jack & Jill bathrooms, this spacious abode provides ample accommodation...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kahuku, Hawaii

Rainbow Hale Estate Ka'anapali - Luxury Oceanview Estate with Pool & Hot Tub

Set on 5.13 acres within the gated Kaanapali Coffee Farms, this single-level estate offers sweeping ocean views, three king suites and a convertible den to accommodate up to 8 guests. The gourmet kitchen features a built-in espresso machine; the saltwater infinity pool,...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Lahaina, Hawaii

One Ocean Mauna Lani Golf Estate 3

Welcome to 6BD Mauna Lani Lux Golf Estate (3) at One Ocean, a brand-new luxurious six-bedroom, six-and-a-half bathroom home built in 2024, nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Kamuela, Hawaii

Luxury Aloha Escape Turtle Bay - Kuilima Estates West

Stay comfortably in Kahuku at this 2-bedroom condo. Experience the enchanting atmosphere of this cozy retreat, complete with a king bed and a twin bed. Enjoy the peaceful surroundings and modern amenities like WiFi, AC, and a washing machine. Relax in the living room...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kahuku, Hawaii

Legendary Estate 50 Steps to Maui's Best Beach! New! 5 Bedroom, Pool with Slide!

Have you been dreaming about the ultimate Hawaii family vacation? Do you dream of a property that sits across the street from the top beach on Maui? Welcome to this incredible estateAs one of the only properties on Maui this close to an impeccable sandy beach, you'll...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 18
📍 Lahaina, Hawaii

Sky Villa Estate: Luxury Gated Kona Retreat with Ocean Views

Welcome to your Hawaiian haven, Sky Villa Estate! Kick off your flip-flops and let alohaspirit guide you up the driveway to this secluded gated 5-acre estate, through lushlandscape that feels like a warm hug from the island itself. Deep lush lawns encouragefamily games...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Waiulu Estate Villa - Waiulu Golf & Oceanview Estate Hualalai

Welcome to the exquisite Waiulu Estate Villa at Four Seasons Hualalai Resort. This estate offers a private and serene setting with close wide-open ocean views. The estate has been recently updated with new contemporary décor by the renowned Henderson Design Group....

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Relax in this OceanView Estate w/ Lava stone-lined Infinity Pool & Private Spa

The Hualalai Resort will host the annual Chairman’s Club 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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kailua Kona, Hawaii

122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai

The Hualalai Resort will host the annual Chairman’s Club 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...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua Kona, Hawaii

Four Seasons Hualalai 5BR Ocean Estate

Escape to your own private paradise at this stunning newly renovated expansive 5 bedroom, 5 bathroom 6500 square foot ocean adjacent estate, a beautiful custom home on 3/4 of an acre, nestled within the exclusive Four Seasons Resort Hualalai. Experience the height of...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 14
📍 Kailua-Kona, Hawaii

Honu Hale on Turtle bay golf course - Kuilima Estates West

2 bed 2 bath condo with a loft. Sleeps 4 people. Explore Oahu and enjoy North Shore's beautiful ocean. Just a 8 minute walk to the relaxing beaches of Turtle Bay Resort. A short 5-15 min drive to many legendary beaches with soft sand, turquoise water, & amazing waves!...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

Makanui Estate - AC, Sleeps 17

MAKANUI ESTATE AT KOLOA KAI VACATION RENTALSA Private Paradise for Your Kauai EscapeWelcome to Makanui Estate, a luxurious retreat in the heart of Poipu offering breathtaking ocean views, serene mountain backdrops, and spacious accommodations for your family or group....

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 17
📍 Koloa, Hawaii

Hale Pahonu – Secluded Polynesian Beachfront Estate in Waimanalo

Make unforgettable memories in this secluded, polynesian-styled beachfront estate situated on the eastern side of Oahu next door to the famous Magnum PI Robin's nest. Flanked by the majestic Ko’olau mountains on one side and a reef-protected lagoon and beach on the...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Waimanalo, Hawaii

Hale Keaka: Luxury Modern Estate w/ Pool, Outdoor Showers, Hot Tub & Ocean Views

Immerse yourself in the pinnacle of luxury at Hale Keaka at Kukuiula by Gather, a striking 6BR/6.5BA estate in Koloa, Hawaii, perfect for up to 14 guests seeking a sumptuous south shore Kauaʻi vacation.Step into Hale Keaka at Kukuiula, a brand-new luxury estate...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Koloa, Hawaii

Maka Nui Estate private family resort style home.

Maka Nui Estate: Luxurious Oceanfront Paradise in Captain Cook, Hawaii.Aloha and Welcome to Maka Nui where big views meet unforgettable moments!Perched on a dramatic cliffside at 1,000 feet elevation, Maka Nui Estate, meaning Big View, offers sweeping vistas of...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Captain Cook, Hawaii

Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC

We invite you to sit back, relax and experience the dazzling sunsets, tropical breezes and never ending ocean views from "Mango Sunsets", our private 3-acre Kohala Ranch estate where modern elegance meets traditional quality craftsmanship. This previous popular vacation...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kamuela, Hawaii

Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles

Our home was updated during the last half of 2021 and in early 2022 with new cabinets, countertops, appliances, sinks, faucets and dimmable recessed lighting in kitchen, baths, wet-bar and laundry; all new showers and a free-standing tub in the baths; all new walnut...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Lahaina, Hawaii

Kilauea Lakeside Estate - Secluded Luxury Retreat on Private 4-Acre Peninsula

This totally private resort has been described as the best private Kauai retreat in the Hawaiian islands. Located in a wildlife refuge on its own private lake on the island of Kauai, Kilauea Lakeside Estate is a beautifully secluded Hawaiian retreat, simply perfect for...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kilauea, Hawaii

Breathtaking Ocean, Kohala Coast, 4 Volcano Views, Fountains, Pool, Spa, Estate

FALL SPECIAL!!! 20% for the month of October or November, 2025. Book at least 30 days between October 4th through November 7th or 30 days between November 4th through December 8th to get 20% off the published rate on VRBO. That's an addition 10% off on top of the 10%...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 9
📍 Kamuela, Hawaii

Guest House on gorgeous tropical private 3 acre estate perfect central location.

Located on the Big Island of Hawaii, this detached studio guest house is fully furnished, very private, with vaulted ceilings on a beautifully landscaped 3 acre privately enclosed property. Property has a gated entrance with private gate code, grounds security system,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 5
📍 Keaau, Hawaii

Luxury home on a 2-acre gated estate in Central Oahu

Escape to a secured and quiet environment after a day of fun and madness. Just 33 minutes to Waikiki * 30 minutes to the North Shore, this newly renovated executive home has split AC & heat in every room * fitness gym * large covered patio for BBQ * modern kitchen *...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Wahiawa, Hawaii

Hale Laule'a - North Shore Oahu Estate. Walk to Sunset Beach!

**In compliance with Hawaii vacation rental laws, this property is held for your exclusive use for a period of 30 days or greater regardless of your actual length of stay. Please inquire for details or questions regarding pricing and availability. Total pricing for the...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 9
📍 Haleiwa, Hawaii

SEArider ONE at Turtle Bay (2 bedroom / 2 bath) - Kuilima Estates East

~ You just found your Base Camp to explore the North Shore of Oahu ~Our condo has just been completely remodeled and redecorated with two brand new bathrooms as of September 2021. We are situated alongside the Palmer Golf Course and are a short 5-10 minute walk to the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kahuku, Hawaii

Perch - Kihei Garden Estates

Discover beachside bliss in Kihei! this enchanting home captivates with its blend of cozy ambiance and unbeatable location. Steps away, discover a plethora of restaurants, shopping, dining, and coffee spots, all within walking distance. This tranquil refuge offers a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

Noiulu One – Brand New Hualalai Estate

Located in the exclusive Noi‘ulu Estates neighborhood, this brand new 6 bedroom, 6.5 bathroom custom gated estate home offers an expansive luxury residential experience highlighted by majestic ocean views. Abundant natural light accentuates modern, natural finishes...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Kailua Kona, Hawaii

Jungle Bee: 23 Acre Estate on Kauai's North Shore with Private Beach Access

GE/TA 125-285-3760-01TA#W90869281-01Permits: TVNC 4272 SP2012-10Welcome to Jungle Bee!Note: Pricing includes both homes on the property and exclusive use of the estate.Jungle Bee Farms is a stunning 23 acre estate overlooking the northern most point in the Hawaiian...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kilauea, Hawaii

Kai Moena Estate - Kailua Luxury Beachfront Estate with Pool, Spa, AC, Sauna, Fitness Center & More!

Prices start at $100,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. This luxury...

🛏 7 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii

Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Situated in the famed oceanside neighborhood...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Honolulu, Hawaii

Garuda Estate – Launiupoko Luxury Home

We invite you to indulge in this magnificent 3,300-square-foot villa nestled at the bottom of the Mountains of West Maui, Launiupoko. It's the first town off the bypass. A short 15-minute drive takes you into Ka'anapali. Whalers Village offers a golf course,...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Launiupoko, Hawaii

SEArider TWO at Turtle Bay (1 bedroom / 1 bath) - Kuilima Estates East

Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kahuku, Hawaii

Estate on Tropical Acre - Harmony in Paradise

Modern home, over 3,500 sq ft; a resort-quality property that can sleep up to 10 guests, on an amazingly lush, fully-landscaped acre. Large living room, exceptional kitchen and dining areas, four lovely bedrooms, a study has been equipped with children in mind, and...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Keaau, Hawaii

Grand Oceanfront Gated Estate on the Hamakua Coast.

Experience the magic of this breathtaking oceanfront gated estate. Watch dolphins, whales, and cruise ships sail by. Feel the cooling Tradewinds where they first reach the Hawaiian Islands on your skin. Located in the heart of the Hamakua Coast, this is more than a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Hakalau, Hawaii

Beachfront Estate On The North Shore with AIR CONDITIONING 90/TVU-0043

Hukilau Beach and the blue waters of the Pacific Ocean on one side and the Ko'olau mountains on the other, Hale Lani lives up to its name as the “House of Heaven.” The perfect choice if you’re traveling with a large family or a group of friends, this home is one...

🛏 6 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 14
📍 Laie, Hawaii

Hilo's most secluded luxurious ocean front estate

Hale Hokulea - Private Oceanfront Estate on 16 Acres Welcome to one of Hawaii’s most secluded luxurious ocean front estates!Our family vacation home is situated on a 16-acre heart of palm plantation along the Scenic Route. As you enter the gated estate, you will feel...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Papaikou, Hawaii

Kona Beach Estate - Oceanfront, Pool, Aircon, Sunsets, Ideal for celebrations

Welcome to Kona Beach Estate, a luxurious oceanfront retreat nestled along the stunning Kona coast. Located on Ali’i Drive, this private, gated estate offers a serene and stylish getaway just minutes from downtown Kona. Perfect for multigenerational family vacations,...

🛏 5 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Holualoa, Hawaii

Luxurious Golf Course Ko Olina Kai Estates Getaway w/Parking & Near the Beach

This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.This property is located at 92-1043 Koio Drive.This enchanting second floor home away from home is situated...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kapolei, Hawaii

Cottage on Beachfront Estate property, central Hanalei Bay

This amazing and completely refurbished home is situated on a stunningly beautiful one-acre, gated OCEANFRONT estate property, right in the middle of magical Hanalei Bay. It is, in fact, one of the ONLY vacation rental cottages on beachfront property to be found...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Hanalei, Hawaii

Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate

Experience island lifestyle in one of Kona's most desirable gated communities: Keauhou Estates.Amazing home with 3 bedroom with 3 and 1/2 baths. Beautiful great room, dinning room and gourmet kitchen overlook the pool to the ocean beyond. Imagine a beverage and sunset...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kailua Kona, Hawaii

Spacious 3 Bed 2.5 Bath House in Kahakai Estates

Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a

***Please note there is a 7-night minimum during the holidays. Christmas reservations must check out by 10 AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14-night minimum to book both Christmas and New Year's.***...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua Kona, Hawaii

Pole House On Wooded Estate With Fabulous Coastline And Mountain Views

As of April 1, 2020, our guesthouse is now only available as a long term rental (6 month/180 days or more).Our guesthouse is nestled along the slopes of Mount Hualalai on our 40 acre ranch and coffee estate. Located above the historic and scenic Mamalahoa Highway and 2...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Holualoa, Hawaii

Niki Lani Condo on the Golf course @ Turtle bay - Kuilima Estates West

*Newly renovated* 3 bed 2 bath beach condo that Sleeps 10+. Make this Island Oaisis yours! Discover O'ahu and enjoy the beautiful North Shore! Just a 5 minute walk to the relaxing beaches of Turtle bay and a 5-15 min drive to many legendary beaches with soft sand,...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 12
📍 Kahuku, Hawaii

Hale Kahili Nui – Poipu Beach Estates Luxury Villa

For those desiring larger accommodations, Hale Kahili Nui able to be combined with Hale Kahili Ohana for a Hale Kahili 8 Bedroom Estate experience.Amazingly spacious and extraordinarily appealing, this newly constructed 2-story villa is conveniently located in Poipu...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Koloa, Hawaii

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