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.
Beautiful Oceanfront Estate with heated saltwater pool, Hamakua Coast Acreage.
Summary:You found a perfect balance of comfort, style, and location. This home blends natural finishes with calming treehouse vibes, offering a peaceful escape just minutes from Hilo on the Hamakua Coast. Enjoy a kitchen, lux bathroom, smart TV, and cozy seating for...
Hoku Hale – Ainamalu at Waikoloa Beach Resort
***Luxury Golf Course Estate with Private Pool, Daily Hilton Waikoloa Pool Access, Concierge Services & Game Room | Sleeps 10+ in Waikoloa Beach Resort***Welcome to Hoku Hale at Ainamalu, your ultimate luxury retreat nestled in the heart of Waikoloa Beach Resort....
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...
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...
NEW! 3/BR Coffee Estate with Hot Tub and Ocean View in Kona town
Aloha!! We are new to VRBO but have 25+ 5 star reviews on another popular vacation rental platform. This is truly a unique property and I have no doubt that you will enjoy your stay! This Kona coffee estate is located just minutes from downtown Kona. Centrally located,...
Paradise on park like estate with beautiful ocean and mountain view
Envision time on 45 acres of a landscaped park-like estate bordered by two streams - one is seasonal with a forty foot waterfall. Imagine picnicking by the stream or going for leisurely walks. The 800 plus square foot guest house provides privacy and space to relax....
Hale Ohia – Private Gated Luxury Estate with Panoramic Ocean Views
Kauai's Premiere Vacation Rental - "Hale Ohia" This private and gated custom estate is like no other. Four suites with private baths lends this home to have constant ocean views. The exceptional out door living area - "Pai Pai" has 2 large drop down TV's for watching...
Pineapple House: Ocean View Home in Keauhou Estates w/ Private Hot Tub, BBQ & AC
This elegant 3-bedroom, 2-bath home in the gated Keauhou Estates blends spacious island living with serene privacy. Set on the ground level with tropical gardens, city views, and a glimpse of the Pacific, it offers a refined retreat just minutes from downtown...
Luxe Golf Estate w/ Hilton Pool passes - Sleeps 10
Luxury Meets Paradise: Nohea Hale in Waikoloa Beach Resort – Top 5% Airbnb Guest Favorite!Welcome to Nohea Hale, a luxury 4-bedroom, 4-bathroom Five-Star estate located in the prestigious Ainamalu community at Waikoloa Beach Resort. Ranked in the top 5% of Airbnb guest...
102 Hainoa: Ultra Luxe Oceanview Estate at Hualalai with Private Pool & Spa
Important Resort 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...
Kona Hillside Estate - Gated Property with Lap Pool
Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...
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,...
Beach Cozy North Shore Turtle Bay Condo - Kuilima Estates East
Summary:Welcome to our little slice of paradise on the North Shore of Oahu, Hawaii. Our beach cozy condo is nestled in a well maintained gated community at the famous Turtle Bay Resort. Whether you are looking to relax or enjoy adventurous activities, this is the...
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...
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, and the...
Turtle Bay Condo- Kuilima Estates
Ground floor end unit, located on the 18th hole of the world re-nowned Turtle Bay resort! King sized bed in bedroom, 1 queen Murphy bed and 1 queen sofa bed in living room. AC in both bedroom and living room. Screened-in lanai. A nice walk away Turtle bay resort, coved...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
Important Resort 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...
Trivett Oceanfront Estate: 5BR Luxury Retreat in Kailua-Kona
STVR- 19-365146NUCR 20-1787TMK - (3) 7-5-005-096GE/TAT - 051-694-0288-01Transcend paradise with our absolute oceanfront 3 story 5 bedroom home located only blocks to Kailua-Kona town and within a guarded gate community of luxury estates. Your private oceanfront setting...
Hale Waima Lani - Luxury Oceanfront Estate in Puako
Modern luxury and old Hawaii charm meet and beckon from one of the largest oceanfront lots in Puako. With 350+ feet of beachfront access and ocean views from every room, this unique and meticulously maintained home is a vacation dream—the main hale with a luxury...
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...
Spacious 3 Bed 2.5 Bath House in Kahakai Estates
Experience island living at its finest in this beautiful and modern 3-bedroom, 2.5-bath home located in a quiet, gated community just minutes from downtown Kailua-Kona. Enjoy easy access to beaches, shopping, and restaurants—then return to your private oasis complete...
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...
Gorgeous North Shore Kauai Estate with Saltwater Pool
Bright, cheerful and tastefully designed, this 5 bedroom home sleeps 10 comfortably. Each room has its own unique personality, while the estate is coordinated with aquamarine color schemes, hardwood accents and inspiring details. Cooking for many is an easy task with a...
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...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Gorgeous and High end 4 bedroom plus bonus (sleeping) loft home. Located in a prime gated community, sleeps 12. Sleeping cots available if needed. The home has a Tropical landscaped yard, fantastic ocean view from both lanais, central A/C, plunge pool with a water...
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...
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,...
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...
New Luxury 5BR Princeville Estate with Pool
This Luxury Pool & Spa Estate has it all! Panoramic Views of Hanalei Bay, Lumahai Beach, Bali Hai, Mountains, Waterfalls, Rainbows, backing to hundreds of tropical acres and fruit trees! 5 Bedrooms, 5.5 Baths, Separate Living Room with 85" HDTV, Fully Equipped Gourmet...
Turtle Bay Hideaway - Kuilima Estates East
Our Turtle Bay Hideaway is the perfect place for your Hawaiian getaway! Enjoy 5 miles+ of secluded beaches, 2 private swimming pools, 2 private tennis courts, 2 PGA golf courses, horseback riding, surfing, snorkeling, diving, fishing, activity rentals and fine dining...
Kailua-Kona Luxury Vacation Home – Ultra Private Oceanfront Gated Estate
This oceanfront residence is a gated estate situated in a private neighborhood off of Kailua-Kona’s scenic Ali’i Drive, just 5 minutes from town. Recently remodeled, this home reflects a true sense of place with Hawaii-style architecture, expansive indoor-outdoor living...
Kai Hale: 3 BR Oceanfront Lanikai Beach Estate
AlohaRelax and unwind at Kai Hale. This beautiful Lanikai ocean front home is directly in front of the Mokulua Islands.This location is suited for year round living and is ideal for stand-up paddling, kayaking, boogie boarding, snorkeling, and children's activities. A...
Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai
Important Resort 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...
Kuilima Estates West - 3 Bedroom Vacation Home
NEW LISTING! This newly renovated 2-story 3 bedroom condo is located at Turtle Bay in the gated community. This is the ONLY condo with split AC downstairs and central AC upstairs. This beautiful island condo sleeps 8 guests.This condo is just steps away to two...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
This expansive oceanfront estate, Maunalua Sunset, sits on a rare double-wide lot along the calm shoreline of Maunalua Bay in Portlock. Multiple standalone structures wrap around a lush courtyard and resort-style pool, creating a private sanctuary designed for extended...
Hale Koolau Estate - Private Retreat in Haena with Hot Tub & AC
Hale Koolau Estate (Main House + Treehouse), Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018Transient vacation rental is located in the tsunami evacuation zoneOn the north shore of Kauai, Hale Koolau Estate sits behind wooden gates and...
Serene Pakui Pua Estate at Hualalai with Saltwater Pool & Personal Concierge
Imagine stepping into your own Hawaiian sanctuary at Serene Pakui Pua Estate, where tranquility greets you in Hualalai Resort’s exclusive Kauhale neighborhood. Wake in the Grand Master Suite, ocean and Maui views filling your sight, and slip into the tropical outdoor...
Hale Minoaka Main by Destination Kauai - Poipu Beach Estates, A/C
🌺 E Komo Mai — Welcome to Hale Minoaka Main House | Private Poipu Retreat with Hot Tub & A/CDiscover island comfort and relaxation at Hale Minoaka Main House, a beautifully appointed 1-bedroom private home located in the prestigious Poipu Beach Estates neighborhood on...
Waipio's Enchanted and Private Hideaway Pool, Slide, Hot tub & Spectacular Views
Waipio Heaven – Cliffside Luxury Estate with Ocean Views, Pool, & OrchardLocation: Hamakua Coast, Big Island, Hawaii Bedrooms: 4 | Bathrooms: 4.5 | Sleeps:** 10 Minimum Stay: 5 nightsProperty Overview:Discover Waipio Heaven, a private, luxury 4-bedroom estate nestled...
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...
Stunning Ocean View In Luxury Home In Keauhou Estates
Enjoy spectacular 180-degree ocean views from this 3 bedroom, 3700 square foot luxury home in Keauhou Estates on the Big Island of Hawaii. The house has an open floor plan, marble floors throughout most of the main living spaces, and large rooms with tasteful and...
A 5-Star Estate, Large Groups, Luxury Living
This luxury condo is situated a short walk from the beauty of the beach! A 3,700 square foot, 3 bedroom, 3.5 bath gem, it is the ideal place for a quiet retreat. Features a Master Suite with private lanai and two additional bedrooms with en suite baths, sleeping up to a...
The Bluffs 22 – The Beach House Opulent Oceanview Luxe Estate
Nestled on over an acre within the prestigious Bluffs enclave on the Kohala Coast, Mauna Kea Resort Bluffs 22 – The Beach House is an oceanview estate where curated design, effortless luxury, and authentic island living flow together in perfect balance. With 8,141...
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...
Waiulu Tropical Sanctuary: A Luxury Oceanview Estate at Hualalai
Imagine waking in the primary suite of Waiulu Tropical Sanctuary, where collapsible walls vanish to reveal ocean breezes and poolside serenity—a magical start to your Hualalai escape. Masterfully redesigned by Henderson Design Group, this 4-bedroom estate, with a...
Artevilla at Pauoa Beach - Luxury Estate with Private Pool & Club Perks
Welcome to Artevilla at Pauoa Beach, the best of modern living in a classic Hawaiian setting.Nestled adjacent to the renowned Fairmont Orchid 5-star Hotel and Mauna Lani, Auberge Resorts Collection, Artevilla is a lavish two-story villa offering unrivaled luxury....
Moana Makai & Moana Mauka – Kailua-Kona Oceanfront Estate
We are 2 luxury oceanfront vacation rentals on the Kona Coast. Voted "Best Private Estate in - Kailua Kona Hawaii" October 1, 2016 These two beautiful homes share the estate’s lava rock saltwater pool and jacuzzi, lushly landscaped yard overlooking the Pacific ocean,...
SPRING BREAK SPECIAL! Lau'eki Estate ~ Hualalai ~ Sweeping Views ~ Infinity pool
Step through a tropical courtyard into Elegant Lalani Lau’eki Estate, a 4-bedroom retreat with a separate Ohana guesthouse, ideal for couple getaways or family gatherings. A breathtaking hallway frames ocean views from the expansive lanai, where you’ll sip coffee as the...
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 of only...
Volcano Rainforest Estate & Lodge; 5 miles to National Park; Hot Tub; 3 BR/3BA<br>11-3203 Huakai Street, Volcano, HI, 96785, United States
ENTIRE MAIN HOUSE RENTALOwner Hosted, owner's cottage is located on the property down a separate drive, privacy for guests in main house.The Volcano Rainforest Lodge is a luxury craftsman house in an ancient forest. We are located only a few minutes from the Hawaii...