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.
Unparalleled Luxury Across Hawaii's Premier Islands
Our portfolio of Hawaii luxury vacation rentals spans the state's most breathtaking destinations. Whether you're drawn to the calm, turquoise bays of Oahu, the dramatic cliffs of Kauai, the golden beaches of Maui, or the lava-sculpted coastlines of the Big Island - our luxury estates deliver style, privacy, and location.
Each vacation home is hand-selected to provide an exceptional island experience, from beachfront villas with private pools to mountain-view estates with outdoor showers and chef kitchens. Whether you're planning a honeymoon, corporate retreat, or a multi-family getaway, we offer high-end homes to match your vision.
Designed for Comfort and Sophistication
Our exclusive Hawaii vacation homes offer more than just square footage. Expect upscale features like smart-home automation, spa-inspired bathrooms, media rooms, and expansive lanais with al fresco dining areas. Many properties are located in gated communities and come with access to resort amenities, private chefs, or concierge services upon request.
Popular Features in High-End Hawaii Rentals
- Oceanfront locations and panoramic coastal views
- Infinity-edge pools, hot tubs, and outdoor lounges
- Large gourmet kitchens with wine storage and island seating
- Multi-level floor plans for large groups and family gatherings
- Beach gear, kayaks, paddleboards, and snorkeling equipment included
- Optional housekeeping, grocery pre-stocking, or spa services
Perfect for Every Occasion
Our luxury vacation homes are frequently booked for destination weddings, executive retreats, anniversaries, and seasonal escapes. With properties offering between 3 and 8+ bedrooms, you'll find the space and elegance needed for any group size or travel style.
Book with Confidence
To-Hawaii.com features a curated selection of luxury vacation homes available across the Hawaiian Islands. From beachfront estates to private resort villas, explore high-end properties that combine style, comfort, and unforgettable island experiences.
Kahala Hills Estate by Gather: Luxury Oceanview Villa w/ Pool & Gym
Kahala Hills Estate rises above Honolulu on the ridge of Waialae Iki, offering a private three-story retreat surrounded by palms, sculpted gardens, and wide ocean horizons. The 4,007-square-foot luxury residence sits on an 18,000-plus-square-foot lot, blending bold...
NEW! KBM Resorts West 35 | FREE CAR | Kuilima Estates | 1-Bedroom Condo at Turtle Bay! KUL-W35
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Diamond Head Luxury Beachfront Estate
This award-winning oceanfront residence, Diamond Head Grand Escape, offers a rare opportunity to experience contemporary Hawaiian living in one of Honolulu’s most coveted enclaves. Set directly on the sand within the exclusive Cove area of Diamond Head, this home is one...
Private Ocean Front Estate on Turtle Cove, Napili - Most Spectacular Location
THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES,WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING,TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna ....Locals tell us Papaua Paradise is the best location on Maui. We are located at...
Welcome to Wainani Sunset Estate – your island home away from home. This retreat features four suites with walk-in closets, en-suite baths, and split AC. Cook and gather in the open kitchen and dining area, then step outside to the lanai with BBQ, lounge, and fire-pit...
Hale Hanohano by Gather: Luxury Poipu Estate w/ Pool, Spa, Lanais & Ocean Views
A statement of island elegance in Koloa’s sun-drenched Poipu district, Hale Hanohano at Kukuiula is a 6-bedroom, 5.5-bath luxury estate designed for seamless indoor–outdoor living and panoramic ocean, mountain, and golf course views. With over 5,200 square feet of...
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of sand. Blending timeless coastal architecture with luxurious modern amenities, this 5,902-square-foot residence offers the...
Luxury 6BR Ocean View Estate Home in Kukuiula
Framed by panoramic ocean views and painted sunsets over Popiu, this single-story, 6 bedroom luxury vacation home captures the essence of sophisticated island living. The home's southwest-facing orientation welcomes golden light throughout the day, transitioning...
6Acres- 6 Bedrms- Soccer Field- Trails- Baths- SwingsWelcome to this special, 6-acre, very private, Keaau country estate. - 6-bedrm, 3-bath - 2 Level Floor Plan - Sleeps 14 - 🥅Soccer Field - Walking Trails - Playground Swings & Large Fields - 🔥Fire Pit at the "Fire...
Hawaiian Pakele-Ocean View Estate
Aloha and welcome to our home!! Newly built and luxuriously appointed, this beautiful 3 bedroom and 2.5 bathroom house is the ideal spot on the west side of Oahu. Located in the private gated community, with breath taking views of ocean and mountains and only a 3-min...
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Welcome to our luxury 3BR/3BA estate in Poipu Beach Estates, just ½ mile from the beach. Perfect for families or groups, the property offers a beautiful common area with 2 large outdoor Lanais. Enjoy AC in each of the bedrooms, premium kitchen with quartz, and modern...
Manoa Royal Retreat by Gather | Luxury 9-Acre Estate w/ Pool, Views & Trails
Manoa Royal Retreat is a rare 9-acre Honolulu estate where contemporary design meets lush Hawaiian mountain serenity. This three-story sanctuary sits high above the city with unobstructed views of the ocean, coastline, mountains, and sunsets. Designed by award-winning...
Most Expensive Luxurious Oceanfront Estate on Makena Beach-6BR/7.5BA 8,030 Sq Ft
Step into island luxury at this breathtaking oceanfront estate on Makena Beach, one of Maui’s most exclusive and pristine stretches of coastline. With 8,030 square feet of elegantly designed living space, 6 spacious bedrooms, and 7.5 bathrooms, this private retreat...
Paradise Beach Estate: 6BR Oceanfront Villa w/ Pool, Spa & Views
Wake up to the sound of surf and the shimmer of the Pacific at Paradise Beach Estate, a six-bedroom, five-and-a-half-bath beachfront sanctuary in Honolulu’s coveted Diamond Head enclave. With 4,705 square feet of airy interiors, resort-style outdoor living, and walk-out...
Oceanfront Poipu Pool Home - Fabulous 7 BR Estate
This beautiful 7 bedroom for 14 oceanfront pool home is only 75 yards to famous Brenneckes Beach! Enjoy uninterrupted sunrise and sunset views from your oceanfront pool and jacuzzi. Enjoy the playfulness of breaching whales and spinner dolphins by day and the quiet calm...
Puna Rainforest Retreat Hot Spring-Ocean views on 20 acre Estate
Enjoy the solitude of Hawaii's rainforest on a lovely 20 acre estate. This ocean view home is super clean and spacious, on gated private property and very comfortable for up to 10 guests. Appreciate the rainforest sounds, rainbows, starry skies and sunshine, far from...
Hualālai Resort Estate | Infinity Pool | Golf & Ocean Views | By Cuvée
The top-ranked villa on the Hualālai Resort golf course, this 6,300 sq ft estate was designed around one idea: dissolve the wall between inside and the Pacific. Cornerless walls, five bedrooms each with private lanais and outdoor shower gardens, an infinity pool, custom...
Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
This large, Hawaiian Style home boasts luxurious indoor and outdoor spaces and stunning ocean views overlooking the 4th hole of the Ke‘olu Course. Five bedroom suites accommodate up to 10 guests plus media room, infinity pool and hot tub and a private courtyard. Located...
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...
Ke Alaula Estate: Hualalai Luxury with Lanai, Heated Pool & Golf Views
Seasonal 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 discretion....
Escape to this spacious 4-bed, 3-bath oceanfront retreat on Oʻahu’s peaceful east side, where golden sunrises and crystal-clear waters await just steps from your door. Sink your toes into the soft white sand right out back, take a morning stroll with coffee in hand, or...
Spacious 6-bedroom beachfront estate with hot tub, AC, near shopping center
Experience what Hauula has to offer with a stay at our estate. This is one of the most unique homes on the entire North Shore. Perfect for large groups who want to be right on the ocean, away from traffic, close to restaurants and grocery stores. It has all the...
Private Diamond Head Estate-walking distance from restaurants, shops and Waikiki
Step into your private tropical sanctuary, nestled at the foothills of Diamond Head. Surrounded by lush landscaping, this newly built estate offers the perfect blend of luxury, privacy, and resort-style living. With over 20,000 square feet of land and over 4,800 square...
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to offer. With luxury and elegance from the moment you pull into the driveway, Hale Waipo’o is sure to be your luxury home away...
Kihei Estates G105 Gorgeous Remodeled Condo
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 1 bedroom 1 bath island oasis unit in the heart of Kihei. Wander right out to the well maintained grounds and...
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North Shore
Welcome to Samurai House by Gather, an extraordinary oceanfront estate on Oahu’s North Shore. This five-bedroom, eight-bathroom retreat blends Japanese-inspired architecture with modern island luxury. With over 5,800 sq. ft. of interior and outdoor living space, Samurai...
Glam Mid Century Modern 4-bedroom oceanfront estate in wonderful Honolulu
30 day minimum rental. YOU are James Bond (or a James Bond villain!) in this oceanfront architectural marvel with its own beach and cove!!! Site of dozens of editorial fashion, film and television shoots. Check out our socials at midcenturyhonolulu. This property was...
Nanea Kai Villa - Luxury Beachfront Estate in Hawaii Kai
At Nanea Kai Villa, ocean breezes, Diamond Head views, and beachfront living come together in a spacious four-bedroom retreat. This two-story estate offers 4,700 sq. ft. of refined island living, complete with a heated saltwater pool, spa, and private beachfront access...
3 Rooms in Estate House with private access to volcanic steam sauna caves!
This Pāhoa estate offers 3 inviting bedrooms, including 2 full beds and 1 king bed. With 3 private bathrooms(one in each room) featuring a relaxing bathtub, guests can unwind in style. The gorgeous property offers the only private volcanic powered steam sauna in the...
Historic Wailuku Inn: 10 Ensuite Bedrooms | Gourmet Chef Breakfast Included
Summary:Welcome to The Historic Wailuku Inn, a beautifully restored 1924 Maui estate with 10 private en-suite bedrooms, lush tropical gardens, and meandering plumeria-lined pathways. Featured by the Wall Street Journal (Apr 18, 2025) as an authentic alternative to...
Waiulu Estate 152B – Ocean View & Fully Renovated | Onsite Staff & Daily Housekeeping
Situated in the coveted Waiulu neighborhood lies this stunning 4 bedroom, 4.5 bathroom fully renovated estate villa home. Luxury finishes, museum quality art and a flexible floor plan combine with a prime ocean view location to deliver the highest level of resort living...
Puka Pa 8 – 4BR Hualalai Estate with Ocean Views, Pool & Golf Carts
This thoughtfully designed 4-bedroom, 4.5 bath home is the ultimate in modern design and construction and just 6 minutes to resort amenities. All four designer-appointed bedrooms are under one roof and ample outdoor space invites activities such as cooking, TV viewing,...
Puka Pa 4 – Hualalai Luxury Estate
This new expansive estate in the Puka Pa neighborhood is located just 6 minutes to the heart of Hualalai. Five bedroom suites wrap up to 10 guests in bright, modern luxury, featuring natural wood and stone throughout. Expansive indoor and outdoor kitchens, vaulted...
Laueki 8 – 4BR Hualalai Luxury Estate
Experience the epitome of luxury and residential living at Hualalai Resort with this very special property. Ideally located to optimize privacy and breathtaking panoramic ocean views, this gated 4-bedroom, 4.5 bath home has been meticulously designed and furnished to...
Konishiki Beachhouse: Luxury 6BR Oceanfront Home with Private Pool & Beach Access
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.Welcome to Konishiki Beachhouse Estate by...
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
Welcome to The Kahala Mansion by Gather, an extraordinary luxury estate along prestigious Kahala Avenue on Oʻahu’s south shore. Just steps from the tranquil beachfront, this grand 9,154-square-foot residence offers refined island living, architectural sophistication,...
Waialua Beachfront Estate – Tranquil North Shore Getaway with Ohana Charm
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.This stunning property is now accepting...
Family Estate in premier neighborhood close to waikiki
kahala home 4,883sf 6 bedrooms 7 bathrooms on 2 levels private gated entry ith video servalliance leading to 10 plus car parking with 3 car garage with pool and poolside kitchen. Gourmet kitchen, upstairs has 4 large bedrooms. Beautiful spacious and convenient getaway...
Hale 'Ae Kai – Balinese-Inspired Oceanfront Estate
Hale 'Ae Kai, is a world class Balinese-inspired estate on 15 acres above the infamous Secret Beach. With views from Bali Hai to the Kilauea Lighthouse, this luxury compound comprises 4 buildings connected by breezeways, surrounded by gardens and ponds. With an...
Ocean Front Pipeline Estate! Front row seat to the Pipeline Masters surf event!
Pipeline living at its best. A definite bucket list dream vacation destination. Facing directly at the famous Banzai Pipeline and Pipeline Backdoor, this home offers a unique spot to watch the most spectacular surfing waves in the world. This home offers all the...
Honeyed Jade: 8 BD Ultra Luxury Oceanfront Diamond Head Estate with Pool & Hot Tub
Honeyed Jade is an enchanting Diamond Head vacation rental estate located on the exquisite island of Oahu. Oahu is an ideal island to visit if you envision yourself amid beautiful Pacific blue waters and within easy access to shopping and first-class restaurants....
Niu Beach Estate – Private Luxury Meets Island Sophistication
Welcome to Niu Beach Estate, a breathtaking 5-bedroom, 5.5-bath modern plantation retreat set along the peaceful southern shores of Oʻahu. Spanning an expansive 7,711 sq ft of indoor–outdoor living, this newly remodeled estate blends contemporary coastal luxury with...
Luxury estate on Wailuku With an adorable view
An extraordinary opportunity to spend a magical vacation at this incredible home. Enjoy panoramic ocean views. Imagine welcoming your family and friends to your island retreat and building a lifetime of memories and watching stunning sunrise day after day. We invite you...
Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore
Welcome to Kailua Beach Villa, a spacious and contemporary oceanfront retreat on Oʻahu’s Eastern Shore. With 5 bedrooms, 5 baths, and 4,000 square feet of airy living space, this private villa blends modern design with barefoot luxury. Step outside to direct beach...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
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.Ranch Beach Estate is a hidden Hawaiian gem,...
Mauna Kea Villa 3003 - Exquisite Gated Private Estate
Wake each morning to the soothing sound of waves and end your days with fiery sunsets over the Pacific—this exceptional ocean view villa offers the perfect blend of privacy, luxury, and location. Nestled in an exclusive enclave just a short 7-minute stroll from the soft...
A private porte-cochere leads you to the luxury and grandeur that is Kahala Place. Steps away from Kahala beach, Waialae Country Club, and The Kahala Hotel -- this is a very special estate. All bedrooms with their own en-suite bedrooms. Master with his and her walk-in...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Perched above the crystalline waters of Lanikai Beach, Lanikai Hillside Estate by Gather is a newly designed 5-bedroom, 5.5-bath luxury retreat with 6,295 sq ft of interior living plus expansive lanai spaces. Floor-to-ceiling glass, an infinity-edge pool, and panoramic...
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
Where timeless Hawaiian charm meets modern sophistication, Kahala Beachside Estate by Gather offers the ultimate oceanfront escape on Oʻahu’s prestigious south shore. Set directly along the sands of Kahala Beach, this magnificent estate spans 7,860 square feet of indoor...
Beach-front Estate - North Shore, private setting, close to Haleiwa & surf spots
Beautiful, private beach-front estate on near-private beach...except for daily turtle visits. Close-to-town convenience but behind the front gate it feels miles away. Spacious open downstairs floor plan with kitchen, dining area and living room. Guest room, office and...