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.
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...
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...
Mauna Kea Villa 3037 - Architectural Island Estate
This dazzling, single-level, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living and Sonos system, a chefs' kitchen with Wolf and Sub-Zero appliances/wine refrigerator, a dining area with adjoining wet bar, a...
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...
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...
Beachfront Family Estate. Great for multiple families.
Nestled in central Kihei on the northern end of picturesque Halama Street, this family-owned, legal short-term rental features two accommodation options on a beachfront property: a two-story building with four individual units and a detached 2-bedroom cottage. Guests...
Papala Place at Kahakai Estates by Gather: Luxe Poolside Oasis
This private four-bedroom retreat within the gated Kahakai Estates blends elegance, space, and island charm. With partial ocean views, lush gardens, and a resort-style pool area, Papala Place offers a serene escape just minutes from Kailua Kona’s beaches, shopping,...
Nakoa Estates | Beach Access, Recent Remodel
Nakoa Estates offers spacious, modern homes just a short walk from the beach. Photos are represent a collection of homes within the estates. Five bedrooms with portable A/C, 3 full baths, large kitchen, and two living areas with one sleeper sofa. Perfect for families...
Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach
Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...
The Bluffs 22 – The Beach House Opulent Oceanview Luxe Estate
Nestled on over an acre in the prestigious Bluffs enclave along the Kohala Coast, The Beach House is an unparalleled sanctuary of luxury and tranquility where indoor-outdoor living takes center stage. This $15 million, 8,141-square-foot estate redefines Hawaiian...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Gorgeous and high end 4 bedroom plus bonus (sleeping) loft, located in prime gated community, sleeps 12. Very large landscaped yard, fantastic ocean view, central A/C, plunge pool, top appliances (sub zero) granite kitchen beautiful bedrooms, fabulous artwork and only a...
Aloha Sands: Luxury Hawaiian Villa - Puako Beachfront
5 STAR REVIEWS! STUNNING VILLA! TASTE OF OLD HAWAII ON THE BEST BEACH IN PUAKO! This lofty and spacious Hawaiian villa lies on the Gold Coast of Hawaii, the sunniest spot in the state. Aloha Sands is also on the best sandy beach in Puako between the Mauna Kea and Mauni...
Beautiful Oceanfront Estate with heated saltwater pool, Hamakua Coast Acreage.
From the moment you arrive, your every care will melt away at this spectacular gated oceanfront estate. The open floor concept, covered outdoor spaces with BBQ, and poolside gathering areas, are ideal for family vacationing. Hear the sounds of the surf along the rugged...
Hale Pakika at Kukui'ula: Exclusive 5BR Estate with Private Pool, Golf & Ocean Vistas
Welcome to Hale Pakika at Kukui’ula by Gather, a five-bedroom, five-and-a-half-bathroom hideaway designed for up to twelve guests. Located off the first tee of the Kukui‘ula Golf Course in Koloa, this 3,500-square-foot single-level estate blends barefoot luxury with...
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...
Dancing Volcano Estate - sleeps 8 Near Hawaii Volcanoes National Park
Dancing Volcano Estate in Volcano, Hawaii is a fantastic place to stay and visit Hawaii Volcanoes National Park just a few minutes drive from our property. Our main house has 3 bedrooms and 2 bathrooms, full kitchen, large dining area, large living area with SMART TV,...
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...
Dolphin House Oceanfront Estate
STVR 19-363225 - NUC 19-1616Picture yourself vacationing in this magnificent and upscale 6,000 square foot oceanfront home. The stunning house is comprised of 4 bedrooms and 4½ baths with a variety of features including an atrium entry with cathedral ceilings,...
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...
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...
One Ocean Mauna Lani Golf Estate 4 with Infinity Pool & Spa
Welcome to 6BD Mauna Lani Lux Golf Estate (4) at One Ocean, a brand-new luxurious six-bedroom, six-and-a-half bathroom home built in 2024 nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...
Brand New 4BR Poipu Beach Estates Home
Be among the first to enjoy this brand-new luxury vacation home in the prestigious Poipu Beach Estates neighborhood. Ideally situated between The Shops at Kukui'ula and Poipu Shopping Village, and just a quick five-minute drive to Poipu Beach, this home offers the...
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...
Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean 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 Laie Beachfront Estate by Gather, a...
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...
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...
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...
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...
Spacious Historic Estate ~ 5 Min Walk to Hilo & Bay Front
Beautifully appointed historic (once King Kamehameha's private lands) 1930s estate in close proximity to beaches, Botanical Gardens, Akaka Falls, and everything HiloTown has to offer! Walk to the Wailuku River & the Hilo Bayfront in only a few minutes from our home....
MauiJOY Villa -Heaven on Earth ~PRIVATE Estate OCEAN Views, Swimming pool.
A PRIVATE ESTATE where you will experience Comfort, Ease, Quality, Carefree, Private, Relaxing, Heaven on Earth. Our permit number is BBKM 2014/0004.We believe in the Malama Hawaii program where visitors are respected as Ohana "family" and they in turn respect the aina...
Luxury townhouse on Turtle Bay - Kuilima Estates West
Aloha my friend! We invite you to come and experience your tropical paradise...your new home away from home at Turtle Bay Kuilima Estates! Located on the North Shore of Oahu at Turtle Bay, this townhome sits on the Championship Fazio Golf Course with a lake view and a...
Ginger Beach House – Anahola Beachfront Estate
Legally licensed short term vacation rental, TVNC#4308 GET Number: GE-136-304-3840-01; TAT Number: TA-136-304-3840-01EXQUISITE FIND!! For those who appreciate the finer things in life, Kauai’s most beloved beach home, known as Ginger Beach House, is your slice of...
Hale Minoaka by Destination Kauai - Poipu Beach Estates Exquisite Cottage
E Komo Mai – Welcome to Hale Minoaka!Your serene South Shore retreat in sunny Poipu.Nestled in the prestigious Poipu Beach Estates neighborhood, Hale Minoaka is a thoughtfully designed A/C cooled 1-bedroom, 1-bath private cottage offering the perfect blend of comfort,...
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...
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...
Kihei Garden Estates C-201, Ocean Views, Near the Beach, Renovated, w/ Split AC!
The new roof project will take place on building C from 7/14 to 7/23 and over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------Step into paradise at this beautifully...
Private Garden Cottage on 5 acre country estate /Walk to the Botanic Gardens!
Aloha! Our country estate is in Onomea, 6 miles north of Hilo, on 5 tropical acres with garden and ocean views. Onomea Guest Suite is a private cottage with garden views of flowering royal Poinciana trees, sweeping monkey pod trees, mango, lychee, mountain apple trees,...
Luxury Mountainview Estate w/Shared Pools/Spa, BBQ Area & AC - Kamilo #407
This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.Lovely Mauna Lani KaMilo Home 407 is ideally located in a low-density gated community within the Mauna Lani Resort, on the west coast of the Big Island of Hawaii. This...
Kihei Garden Estates B-103 - Modern Design, Bright & Clean, Concrete Floors, AC!
The new roof project will take place over the pool area from 7/18/25 to 7/27/25. During this time there will be noise and debris surrounding the building.------------------------------------From the front door, a magical stretch of Maui beach awaits your exploration -...
Turtle Bay Corner Condo Overlooking the Fairway - Kuilima Estates East
Enjoy the best of what the ‘fabled North Shore’ has to offer in this authentically designed Hawaiian-beach-themed unit, that sleeps up to four (4) adults, with Resort-style amenities at your doorstep, including snorkeling beach access, swimming pool, tennis courts,...
Amazing Turtle Bay Condo - Kuilima Estates East
Look no further for your perfect escape to Hawaii! Nestled in the resort community of Turtle Bay, this newly updated 1 bedroom condo w/ a loft is outfitted with LUTRON Ketra lighting technology & LUTRON motorized shades and can easily sleep 4-5 guests the Kuilima...
Blue Oasis - Champion Ridge Estate at Mauna Lani Resort
Experience the best of Hawaii in this luxury 5,600 sq ft estate in the Mauna Lani resort area. Take a dip in the heated pool and hot tub (heated to your desired temperature), drink a beer in the billiards room, have an evening putting competition on the private putting...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Our very private home, a spacious, 3,500 sq. ft. oceanfront estate, sits on 2/3rds of an acre. It has a large indoor living area, plus an expansive outdoor living area, featuring a 1,000 sq. ft. covered ocean view terrace with a large seating area, a dining table...
Spacious 2 bedroom 2 bathroom on North Shore - Kuilima Estates West
You will enjoy relaxing in this spacious 2 bedroom, 2 bathroom townhome located on the first fairway of the Fazio Golf Course at the Turtle Bay Resort! Beautiful golf course views with ocean view right past the golf course. You may even see some horses grazing in the...
HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH
ALOHA & WE WELCOME YOU TO OUR COMFORTABLE HOME AWAY FROM HOME! LOCATED IN THE SUNNY SOUTH SIDE OF THE GARDEN ISLAND OF KAUAI IN POIPU BEACH, THESE 2 HOMES HAVE BEEN RECENTLY CONSTRUCTED WITH TOP OF THE LINE FEATURES, PERFECT FOR A PARADISE FAMILY GATHERING OF MULTIPLE...
Palekaiko Estate - Kailua Kona Luxury Home with Ocean View
Palekaiko, meaning paradise, is our 3200+ sq. ft. home away from home situated on over an acre in a gated community. Palekaiko has three bedrooms, three and a half bathrooms, an office and almost 1000 sq. ft. of outdoor living space. On the property, you will enjoy over...
Amazing 180° West Maui Ocean View Estate Pool w/Hot Tub- Central AC
Perched on four lush acres in Launiupoko, this gated estate blends the comfort of a secluded retreat with the feel of a boutique resort. Outside, ocean views stretch toward Moloka’i and Lana’i on the horizon. The main house sleeps 7 across three ensuite bedrooms...
Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and Orchard
The moment you enter the Royal Palm lined driveway of this gorgeous estate, you'll know you have arrived at your new sanctuary! Papa Belle Estate is a 3.5 acre oasis on the South Kona coast offering breathtaking views, wonderful amenities, and lush surroundings.Soak in...
Hale Kahili: 8BR Ocean View Estate w/Pools+Spa!
This spacious, sparkling compound offers ideal large-group accommodations in an idyllic setting. Two elegant new villas nestle on an expansive 1-acre lot, with views that might have been plucked from a rack of curated postcards: glittering swatches of ocean, craggy...
Kuilima Estates West 3 Bedroom
TMK (1)570010290042 Welcome to Kuilima Estates West. Location! Location! Location!Only steps to the grounds of the famous and newly renovated Turtle Bay Hotel on the North Shore. We are a Legal Vacation Rental.The condos are Surrounded by Two Beautifully manicured golf...