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.
Turtle Bay Condo: Hawaiian Style & Cozy - Kuilima Estates East
Our condo was carefully designed and decorated to provide a cozy, Hawaiian home feel. It is located on the North Shore , Oahu, which is famous for Turtle Bay and it's Kuilima Point. Home to the best of Oahu's beaches, surfing, golfing, horseback riding and more. If you...
Hale I'a ~ The House of the Fish - Kuilima Estates West
Spacious Condo on the Fazio Golf Course – Your Perfect North Shore EscapeHale Ia ~ The House of the FishThis charming downstairs condo, perfectly located on the first tee of the prestigious Fazio Golf Course, offers the ultimate getaway for families, couples, or...
Turtle Bay Primrose - Kuilima Estates East
Cozy 1 bedroom 2 bathroom ground floor unit. WIFI. A/C in bedroom, 2 TV's, DVD, screened-in lanai, tropically decorated. Blu-Ray player. Fully equipped kitchen and laundry center. Free parking just outside your door. Wheelchair accessible. Carpet in bedroom and title...
Turtle Bay Condo in Kahuku - Kuilima Estates East
Cozy, spacious 1 bedroom+ loft and 2 bathroom upstairs condo. Air conditioning in the bedroom only but great breeze from lanai and beautiful view of golf course. Free WiFi. Tucked away in quiet location close to pool. Two bathrooms, one on the main floor with tub and...
Turtle Bay Alea: 2 BR, 2 BA Condo in Kahuku - Kuilima Estates West
Lovely condo, tastefully decorated. Window A/C in each bedroom with ceiling fans throughout. Updated modern kitchen with granite countertops and bathrooms renovated in 2018. Wi-Fi with flat screen TV's in both living room and master bedroom. Queen bed in master bedroom...
Turtle Bay Sea Breeze - Kuilima Estates East
Affordable, comfortable second story 1 bedroom + loft and 2 bathroom condo. Nice ceramic tile in the entry, bath, and fully equipped kitchen. Carpet in the living room, bedroom, and loft (September 2019), with spiral staircase. A/C in the bedroom only. Free WiFi....
Honu Hideaway ~ Gold Coast Comfort - Kuilima Estates West
• California King bed• Queen sleeper sofa• Two full bathrooms• Air conditioning in the bedroomTake a rest in this lovely condo after a long day exploring the island. This beautifully decorated one bedroom, two-bathroom unit has not only the perfect location but...
KBM Resorts | FREE CAR | Kuilima Estates | 2-Bedroom Condo at Turtle Bay! KUL-E113
Peaceful 1-bedroom plus loft condo on Oahu's North Shore with golf course views, private lanai, full kitchen, and resort amenities-just minutes from beaches, dining, and scenic island adventures.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Delux, spacious, clean condo with AC @ Kuilima Estates West
Newly remodeled, perfect condition condo with one large bedroom, one recently remodeled bathroom and a living room with a sleeper sofa that looks out to the beautiful, famous Turtle Bay golf course. Also a large, gorgeous kitchen with granite countertops, equip with...
Waterfalling Estate – Iconic Oceanfront Luxury on the Big Island
Waterfalling Estate is an oceanfront compound unlike any other on the Big Island. Nestled clifftop along the breathtaking Hamakua Coast, this hideaway boasts a private 85-foot waterfall, an Olympic pool featuring a two-story waterslide, spa, fully loaded custom gym,...
Turtle Bay Hula House - Kuilima Estates West
Ground Floor. Older unit. A/C in the bedroom. Great rate. On the first fairway of the Fazio Golf Course, steps away from Turtle bay Clubhouse, restaurant and bar and a short walk to the beach and hotel. WiFi. Recently replaced comfortable Queen bed. Kitchen and laundry...
Pu'ukala Sunset Estate w/ Amazing Ocean Views! by RedAwning
Escape to the breathtaking beauty of the Big Island and make your vacationdreams come true in this splendid 3-bedroom, 2-bathroom vacation rental home.Nestled in the heart of Kailua-Kona, this tropical paradise offers an open andspacious interior, complete with all the...
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,...
Niu Beach Estate – Private Luxury Meets Island Sophistication
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.Aloha and welcome to your own private slice of...
Kihei Estates G105 Gorgeous Remodeled Condo Home
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...
Kai Moena Estate - Kailua Luxury Beachfront Compound with Pool, Spa, AC, Sauna, Tennis Court & More!
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.Property is currently for sale. The property...
Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!
Paradise found! This beautiful, new home is situated off a paved road behind a solar powered entry gate, on 3 gorgeous acres. You will feel relaxed the moment you arrive, from our comfortable and welcoming fully furnished lanai to the spacious and well appointed...
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
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.Luxury, Privacy, and Grand-Scale Elegance at...
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...
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...
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...
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
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.Boasting an extraordinary beachfront location,...
Luxurious Hakalau Estate Home Minutes from Hilo
Our Newly Renovated Estate Home in the quiet neighborhood of Hakalau invites our guest to relax and enjoy paradise in luxury. Spacious and open floor plan offers plenty of room to accommodate large groups and gatherings. Air conditioned living spaces and bedrooms. Free...
Mauna Kea Villa 3003 - Exquisite Gated Private Estate
This exquisite, single-level, gated, oceanview private estate offers a sunken great room with sliding glass pocket doors for indoor/outdoor island living, a magnificent kitchen with top-of-the-line appliances, custom cabinetry, and woodwork, as well as a dining table...
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...
Large Estate for 40 guests on Oahu's Windward Coast
Summary:Welcome to the only property on the North Shore capable of hosting 40+ guests in one stunning location! This half-acre private estate features five separate units, each with 3 bedrooms and 1 bathroom, making it perfect for large gatherings. Whether you're...
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...
Hale Lani – 5BR Estate at Hualalai Resort
WHY IT'S SPECIALEvery nuance of Hawaiian paradise is incorporated into this five bedroom, five-and-a-half bathroom estate. The custom-built residence unveils dramatic 180-degree ocean, fairway, Maui and sunset views. The resort residence captures the best of indoor and...
Samurai House - Japanese-Inspired Luxury Estate on Oahu's North Shore
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 Samurai House by GatherSamurai...
Hi6-ST1- The Dolphin Bay Estate
Escape to the enchanting Dolphin Bay Estate, a luxurious vacation rental nestled on the pristine shores of the Big Island, Hawaii. This exquisite property offers the perfect blend of serenity, elegance, and convenience, making it an idyllic retreat for those seeking a...
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...
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...
Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East
Welcome to this charming 1-bedroom condo nestled within a serene community, offering a perfect blend of comfort and recreation. With a spacious bedroom with a king size bed and a convenient pull-out couch, this condo comfortably accommodates up to 4 guests. The condo is...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
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 Lanikai Hillside Estate, a premier...
Ke Alaula Estate: Hualalai Luxury with Lanai, Heated Pool & Golf Views
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...
15% Off Summer Special! Luxury Oceanfront Estate: Ocean House 4BD
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.Oahu's Newest Luxury EstateOcean House is the...
15% Off Summer Special! Luxury Oceanfront Estate: Banyan House 4BD
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.Banyan House is Oahu’s most luxurious...
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...
Ultra-Luxury 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...
Stunning Luxury Family Estate in Kona
In 1998, the Lenett family decided to purchase a plot of land on the beautiful Big Island of Hawai’i, after years of visiting as tourists. The Lenett's, natives of San Francisco, fell in love with the island’s natural beauty, tropical weather, and kind people. For...
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,...
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...