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.
Hale Kailani at Poipu Beach Estates - Walking Distance to Shops, Beaches & Fine Dining!
Welcome to Hale Kailani at Poipu Beach Estates! Kailani means “heavenly waters” in the beautiful Hawaiian language, and you will find just that at this luxurious tropical property. Cascading waterfalls into the heated pool create a soothing ambiance as you enter the...
Seaview Maui – Family Vacation Home in Upcountry Maui
Maui County Rental permit - STPH 2014/0004TA-097-868-8000-01 / GE-097-868-8000-01TMK-270031100000Welcome to Seaview! This is a unique family style vacation home, offering space for up to ten family members or friends to vacation together, with considerable privacy....
Spacious, 5 bd/3 ba home in Orchidland Estates
Modern Contemporary, custom designed and well-built home with full kitchen and dining area, laundry, fireplace, beautiful decks, sleeps 10 comfortably, but can accommodate up to 17. Nestled on a private, landscaped acre of rain forest with many varieties of fruit-trees...
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...
Kuilima West Estates 198B
Surf's up on the North Shore and our condo is ithe perfect place to Hang Ten! You'll appreciate the attention to detail, modern amenities and the chic, decor when you escape to our Surfer's Paradise. Our location provides easy access to the surrounding amenities, and we...
Stunning Kaimupulehu Grand Estate Hualalai
This “Over-the-Top” estate is a resort within a resort! Guests often choose to Opt Out of paying the resort fees and enjoy this quiet retreat without the hustle and bustle of the resort activity. Beautiful infinity pool with sandy beach!Flexible check-in / check-out...
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...
Charming Holualoa Ranching-Era Estate near Kailua and Keauhou. Away from it all!
Gracious comforts of yesteryears and featured in the coffee table book, The Hawaiian House Now, the home is an historic 1895 structure, modified in the 1940s. Retaining the charm of old Hawaii with architecture and furnishings of the day, while satisfying the needs and...
Ocean Front Estate, *Private Pool*, Exclusive Beach Frontage
Live the dream at this oceanfront gem, with wide beach frontage and an inviting courtyard pool that beckons you to experience the ultimate Hawaiian retreat in style. Kick off your shoes and step barefoot off your expansive covered lanai onto a sprawling oceanfront lawn,...
Royal Hawaiian Estate – Oceanfront Luxury in Waimanalo
“Notice: In compliance with the Revised Ordinances of the City and County of Honolulu, the Property will be made available for your use and occupancy for a period of thirty (30) days.” Experience Hawaii in an exquisite beachfront mansion with panoramic ocean views on...
Newly Renovated Stunning Beachfront 5 Bed, 6.5 Bath Estate with Pool, Spa & AC
One of the most stunning homes and locations in Maui. The beachfront home is 'U' shaped, with a spacious lanai area which includes a pool and spa and which overlooks the beach, ocean, and the island of Lanai. Located on a private palm tree lined lane with gated entry,...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10 Night Minimum over the Christmas/New Years Holiday Season at $7,500 per night.Spacious beachfront estate is situated on lush tropical grounds, nestled in...
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-acre landscaped...
Gorgeous Oceanfront Estate, Steps From Beach w/AC & Puako Bay Views: 10D
Welcome to 3BD Estate Home at Puako Bay (10D), a luxurious oceanfront sanctuary on Hawai‘i Island’s sun-drenched Kohala Coast. Set along the sands of Puako Bay, this 2,520-square-foot residence captures breathtaking panoramic views of the Pacific and offers the perfect...
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....
Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a
Step into the beauty of island life at Ohana le'ale'a, a newly built 3-bedroom, 3.5-bath luxury estate in Kona that blends expansive indoor-outdoor living with sweeping Pacific views. With 3,180 square feet of refined design, a private pool and spa, and a game room...
Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC
Perched high above the Kohala Coast, Mango Sunsets welcomes you to a 3-acre private estate where modern elegance meets timeless Hawaiian craftsmanship. Hand-carved Balinese doors open to reveal 2,924 square feet of open living space framed by panoramic ocean, mountain,...
Hale Mana: Luxury 5 BR Kilauea Estate with Pool & Hot Tub
Welcome to Hale Mana, one of Kauai's most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views.If you are looking for Hawaii's best...
Pacific View: 5-Acre Gated West Maui Estate with Pool, Pickleball & Basketball
Pacific View is nestled in the majestic West Maui Mountains, a vast area of lush valleys and cliffs. This lovely 5-acre estate is uniquely situated to capture all of that beautiful West Maui offers.Pacific View is a gated villa offering a generous 4000+ square feet of...
The Home of the Hula Moon – Puako Beachfront Estate
Stately and serene, THE HOME OF THE HULA MOON is one of the most beautiful contemporary oceanfront properties in PUAKO. Each bedroom has a perfect ocean view. Located near the end of the road, you will enjoy year-round sunsets and privacy. Puako probably has the best...
Ho'ohu Nani: Private Ocean View Estate in Poipu with Pool, Jacuzzi & AC
Ho'ohu Nani has Four Bedrooms (2 Master Suites), Den with Fold-Out Couch, Four Full Bathrooms, and Two Half Baths. Ocean Views from Upstairs Living Area and Covered Lanai. The Kitchen includes top-of-the line appliances with a new Wolf Range, beautiful granite counter...
Beach Front Estate With Guest Cottage Sandy Beach Heated Pool/Spa:Please Inquire
30 Night ContractImmerse your family in the breathtaking beauty of Hawaii’s North Shore! Enjoy two fully equipped living spaces with top-notch amenities, ensuring a comfortable and memorable vacation.Unlock the gates to our Sandy Beach and sink your toes into the soft,...
BEACH FRONT ESTATE SANDY BEACH Heated Saline Pool/SPA 360 Views: Please Inquire
30 Night Minimum Contract Required: Please InquireWant to share the magic and beauty of the North Shore with your family?Swing open the gate to our Sandy Beach, sink your toes into the warm, soft white sand, and greet the turtles that come in the afternoon. You might...
Hale Maluhia - Poipu Beach Estates Home with Heated Pool
Enjoy the luxury and comfort of our newest Elite home centrally located in Poipu Beach Estates. This custom home takes full advantage of many views and is also positioned to enjoy the fabulous trade wind breezes. The spacious and open great room has sliding doors that...
Hale A Kai - Oceanfront Luxury Estate in Poipu with Pool & AC
Amazing Kauai oceanfront rentals from Parrish Kauai feature this beautiful home at sunny Poipu Beach. Highlights include Hawaii plantation style design and décor and all the must have comforts, including spectacular ocean views from almost every room, three bedroom...
Blue Lagoon Estate at Mauna Lani Resort
Enjoy the best Hawaii has to offer in this luxury 10,000 sq ft Kona Coast tropical estate on The Big Island in the Champion Ridge enclave of Mauna Lani. Enjoy the private heated lagoon pool and spa and access to many of the Mauna Lani resort area amenities including a...
Breathtaking Ocean, Kohala Coast, 4 Volcano Views, Fountains, Pool, Spa, Estate
Book April 21 through May 21st and get 25% off!!!"HOUSE of SINGING WHALES" is a 3 bed/3 bath 1 acre garden estate with BREATHTAKING EXPANSIVE OCEAN, 4 VOLCANO, and KOHALA COASTLINE views, just 1000 ft from the ocean waves. Relax in this beautiful Hawaiian luxury home,...
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...
Maka Nui Estate: Private Family Resort Style Home
Aloha and welcome to Maka Nui Estate — a private ocean-view retreat perchedabove Kealakekua Bay and in Real Hawaii : Experience the authentic Hawaiian lifestyle, away from the tourist crowds. Embrace the natural beauty and local culture of this unique island paradise. s...
Kona Coast Original Beach Boys 9.5 acre Estate, Pool and Amazing Ocean Views
Kona recalls the Beach Boys playing their pop hits by the pool. The band left but the good vibrations linger. Situated on 9.5 gated acres, gated for with an amazing Hawaiian plantation-style home with separate sleeping quarters and a guest house. Pool hot tub, gas...
Hale Mokulua: Lanikai Multi-Home Estate - Sleeps 14
Welcome to Hale Mokulua; an exclusive, quiet and private home adjacent to the spectacular blue waters of Lanikai Beach. With 3 separate living spaces, this remodeled Lanikai home accommodates up to 14 guests. The main house of consists of 3 bedrooms, 3.5 baths with an...
Beachfront Villa and Guesthouse
Escape to a private Puako beachfront estate & guesthouse on Hawaii’s Big Island. Ocean views, steps from snorkeling, luxury amenities & sunset bliss await.Hale Ama is an Oceanfront home located in the magical Puako on the Big Island of Hawaii. Puako is one of the...
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,...
Beautiful & Spacious upstairs Apt in Poipu Beach Estates! One Bedroom with A/C!
This beautiful upstairs 1 bedroom Ohana is located in Poipu Beach Estates just minutes from all sunny Poipu has to offer. A perfect retreat for a couple looking to find a comfortable place to stay in a charming setting. The bedroom has a Queen bed and brand new Air...
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 breezes.Upon arrival to...
Keauhou Lani: Luxury 4BR Keauhou Estates Ocean View Home
Welcome to Keauhou Lani, an exquisite private residence located in the desirable gated community of Keauhou Estates.Step into the grand entry of Keauhou Lani's 4 bedroom, 3.5 bathrooms, 4,750 sq. ft. home plus, 1,700 sq. ft. covered lanai complete with views of Keauhou...
Hululani Luxury Estate, A/C, Pool and Spectacular Ocean Views
This serene estate is named Hululani, or "Heavenly," for its pristine beauty. This truly fabulous home has awesome, panoramic views of the mountains, Bali Hai and Hanalei Bay from virtually every room as well as from the private, saline swimming pool. Located on a quiet...
Pakala Beach Estate: Island-Style Retreat on Kauai's West Shore
Rates shown are for 8 guests; additional guests up to maximum of 11 are $20/night each. This magnificent, island-style estate truly exceeds all expectations. Located on secluded Pakala's Beach on Kauai's west side, this totally serene property borders an orchard and is...
Beachfront Family Estate. Great for multiple families.
Beachfront Family Retreat in Central KiheiProperty Overview:Nestled in central Kihei on the northern end of picturesque Halama Street, this family-owned, legal short-term rental offers guests an unforgettable beachfront experience. The property features two unique...
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...
Hale Aloha - Large Gated Oceanfront Estate on Aliomanu Bay
Hale Aloha… On The Sand TVNC-4185Anaik Martin, is the property manager, lives nearby and is available 24 hours a day, 7 days a week, (808) 652-3410. Professionally cleaned and disinfected by a licensed company. Contactless check-in. Hale Aloha is located in a Tsunami...
Oceanfront gated estate w/heated saltwater pool.
Summary:Your prefect slice of paradise awaits! Enter the gates of this gorgeous oceanfront estate and let the relaxation begin. Enjoy sweeping Pacific views, wave sounds, and sightings of sea turtles and seasonal whales.Ideal for family, this spacious retreat offers...
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 place...
Davidson Point Beach House: 4BR Oceanfront Kekaha Estate
TVRNC-1099E Komo Mai, Welcome to Davidson Point Beach House!Experience the peace and tranquility of this oceanfront estate size lot offering privacy and a front row seat to the surfers at Davidson's Surf Break. Enjoy views of the island of Ni'ihau in the distance and...
Kauai's Sunny Poipu Beach Estates! A Beautiful Plantation Style home sleeps 8.
Summary:Kauai's Sunny Poipu Beach Estates! A Beautiful 3 bed, 2 bath single-level plantation-style residence near World Class Beaches, Golfing and Shopping.The Space:The residence is designed as a gathering place with an open, airy living area ideal for entertainment of...
Paradisio Ho'o Kumu – Luxury Kukui'ula Oceanfront Estate
A truly stunning oceanfront resort property offering six air-conditioned bedroom suites as well as pool, spa and access to Kukuiula beach park right across the street. Resort living at its best, this casually elegant, island-style private home offers ocean and coastline...
Oceanfront Gated Estate Retreat - Banyan Tree B&B Suite w/ Horses-Beach 10m Walk
Aloha and welcome to our Hawaiian Celebration, our Ho'olaule'a. Hale Laule'a at Opihi Point is a +l$10+M, one-of-a-kind, World Class, 5-acre private, Estate Retreat sitting on the cliff edge of the Pacific Ocean with an unmatched view of the Hamakua Coast. Hale Laule'a...
Turtle Bay Penthouse 164 - Kuilima Estates West
Relax in North Shore Luxury | Kuilima Collection | 146 West1 Bedroom | 1 Bathroom | Sleeps 2 | Golf Course Views + Mountain SerenityWelcome to Kuilima Collection | 146 West, your private North Shore escape nestled within the world-renowned Turtle Bay Resort. This...
New Remodel, Pool, Beach Access, A/C - Kuilima Estates West
Relax and unwind with your family in modern luxury. We’re excited to share with you our newly renovated oceanside condo. Nestled perfectly between the North Shore of Oahu’s world class surfing destinations and world famous golf courses - you’ll never be without endless...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...