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.
BEACH FRONT ESTATE SANDY BEACH Heated Saline Pool/SPA 360 Views: Please Inquire
30 Day Minimum Stay Required: Please InquireShare the romance and beauty of the North Shore with your entire family! Swing open the gate to our Sandy Beach, sink your toes into the white sand and say “Aloha” to the turtles who come to our beach each afternoon, or...
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...
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...
Kauai's Sunny Poipu Beach Estates! A Beautiful Plantation Style home sleeps 8.
The residence is designed as a gathering place with an open, airy living area ideal for entertainment of all kinds. The kitchen features stainless appliances, a generous island and lots of counter and storage space resulting in an excellent setting for creating...
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...
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...
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...
Lodge at Kaloko - Kona Cloud Forest Estate with Pool & Hot Tub
🌴 The Lodge at Kaloko – Luxury Estate in KonaPrivate 5BR villa | Pool | Hot tub | Ocean views | Near Kua BayWelcome to The Lodge at Kaloko, a luxury gated estate in the lush Kona Cloud Forest — just 15 minutes from Manini‘owali Beach (Kua Bay), downtown Kona,...
4 BR Hawaiian Plantation-Style Home with Pickleball Court
Old Hawaii at its best! Enjoy the updated traditional home nestled within a fully enclosed and private one-acre tropical estate! Chase the keiki (kids) or grandkids on the spacious lawns, or just enjoy the many tropical trees and plants—coconut, banana, mango, ulu...
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...
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...
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...
Kahikole Street Estate – Four Seasons Hualalai Home with Pool & Spa
Aloha and welcome to your private oasis at the exquisite 4 bedroom home in Hualalai with amenities at The Four Seasons resort. Spectacular views include an unobstructed ocean panorama and the Kohala Volcano to the north, you also enjoy a front row seat of the 8th hole...
Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai
Important Resort Notices * Hualalai Spa Enhancements (Sept 15 – Mid-Nov 2025): During this period, the resort’s outdoor aqua-thermal areas will be under renovation. Massage, body, and facial treatments will be temporarily relocated to the Makaloa Villa. The infrared...
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...
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,...
Anini Vista Drive Estate - Kauai North Shore Gem
A grand estate centered on a magnificent lagoon-style saltwater pool with two waterfalls, a grotto, hot tub and bridge, Anini Vista Drive Estate is a paradise in its own right. Inviting ocean views and expansive gardens surround the main house and guesthouse, which are...
One Ocean Mauna Lani Golf Estate 3
Experience contemporary island living at its finest at 6BD Mauna Lani Lux Golf Estate (3) at One Ocean, an architectural gem completed in 2024 within the private One Ocean enclave of Mauna Lani Resort. Overlooking lush fairways and partial ocean views, this six-bedroom,...
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...
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...
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...
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...
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....
Kilauea Ocean Bluff Estate – Luxury 2-Bedroom Home with Secluded Beach Access
Escape to this enchanting 12-acre estate with panoramic ocean, mountain, and river views. The main residence, guest bungalows, and bathhouse form a connected compound amid lush gardens. The great room with Teak sliding doors opens to the garden and ocean view. Custom...
Relax in this OceanView Estate w/ Lava stone-lined Infinity Pool & Private Spa
Important Resort Notices• September 15 – Mid-November, 2025: The Hualalai Spa will undergo enhancements to its outdoor aqua-thermal areas. Massage and body treatments will temporarily relocate to the Makaloa Villa. Access to the infrared sauna, hot tub, and pool...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
Important Resort Notices* Hualālai Spa Enhancements (Sept 15 – Mid-Nov 2025): Outdoor aqua-thermal areas will be temporarily closed. Massage and facial treatments will move to the Makaloa Villa, with full access to saunas, hot tubs, and pools maintained.*...
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...
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!...
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....
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28
OHANA RETREAT AT KOLOA KAI VACATION RENTALSYour Ultimate Group Getaway in PoipuWelcome to Ohana Retreat, a one-of-a-kind vacation rental in Poipu that can accommodate up to 28 guests, making it the perfect haven for large family reunions, retreats, or multi-family...
Maka Nui Estate: Private Family Resort Style Home
Aloha and welcome to Maka Nui Estate — a private ocean-view retreat perchedabove Kealakekua Bay on Hawai‘i’s Big Island. Set on five acres of tropical gardens,this newly renovated 5-bedroom estate blends luxury and authenticity — offering guests the serenity of...
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,...
Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles
Our home was updated in 2021 and 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 hardwood flooring throughout with...
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...
Breathtaking Ocean, Kohala Coast, 4 Volcano Views, Fountains, Pool, Spa, Estate
"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, while gazing at spectacular unobstructed sunsets...
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,...
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...
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...
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...
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...
Pohinahina Place – Serene Hualalai Estate with Ocean Views & Private Pool
Pohinahina Place is your private resort retreat. With an incredible view of the Pacific Ocean and overlooking the 5th green of the Hualalai Golf Course, this property is located right in the middle of Hualalai Four Seasons Resort. This beautiful oasis is nestled on a...
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...
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,...
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...
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...
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...
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...
Kona Beach Estate: Oceanfront Home with Pool & Private Beach
This luxury oceanfront vacation rental in Kailua Kona promises an unforgettable experience, blending unparalleled comfort with the natural beauty and vibrant culture of the islands. It's a place where every moment is infused with the spirit of aloha, creating memories...
Kailani Estate: 5BR Luxury Home at Mauna Lani Resort
Brand new contemporary single-story luxury estate located in the exclusive One Ocean community at the Mauna Lani Resort. This expansive 5 bedroom, 5 bath home comfortably sleeps 10 guests and is ideal for a family vacation or as housing for a business group needing...
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...