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.
PRIVATE OCEAN FRONT ESTATE ON TURTLE COVE, NAPILI. nMOST SPECTACULAR LOCATIONn
THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES, WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING, TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna .....
Palione Papalani - Tropical Estate with Lagoon Pool on Kailua Beach
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1787. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
3-bedroom estate in peaceful Haleiwa Hawaii
Haleiwa is waiting for you at this serene 3-bedroom home plus mother-in-law-suite. With 3 queen beds and 1 king bed, this brilliant property offers a cozy retreat for guests. Enjoy the bathtub, hair dryer, and WiFi during your stay. We're happy to assist with any...
Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West
Located on the North Shore of Oahu at Turtle Bay, our condo sits on the Championship Fazio Golf Course. There are multiple walking trails and paths that lead to quiet secluded beaches or world-famous beaches such as Sunset Beach, Waimea Bay, and Pipeline. A large pool...
Pauoa Beach Estate: Stunning Villa with Ocean Views, Pool, Home Theatre + Resort Amenities
Enjoy luxury living and ultimate relaxation at the gorgeous Pauoa Beach Estate. The 4 bedroom, 5.5 bath villa is located in the exclusive oceanfront enclave of Pauoa Beach, a short 800 feet from the sparkling blue Pauoa Bay.Over 1000 square feet of outdoor lanais...
Turtle Bay Hale Lani - Kuilima Estates East
This is a beautiful, modern 1 bedroom w/loft and one and a half bathroom end unit. Unit has updated kitchen cabinets & appliances, ceramic tile floors and granite countertops. The living room has a large flat-screen TV, internet and WIFI, TV in master bedroom as well....
Hale La'i: Dreamy Kona Oceanview Estate with Pool, Spa & AC
Aloha & Welcome to Hale La’i - House of Peace and TranquilityFor years, visitors from around the world have traveled in search of a tropical destination offering a relaxing transcendent experience. Our family has found that here, on the Big Island of Hawaii. We have...
Honu Hale: Exquisite Kona Vacation Home with Pool, Hot Tub & Oversized Chess Set
Aloha and welcome to Honu Hale by Gather, your Hawaiian home away from home. This luxury Kona vacation home is located in an upscale neighborhood just 2 miles away from Magic Sand Beach, Kahaluu Beach Park, and downtown Kona. Honu Hale has 5 bedrooms, 3.5 bathrooms and...
Hale `Ohana ~ Family Home - Kuilima Estates East
Welcome to Hale 'Ohana ~ The Family Home, your idyllic retreat nestled in the heart of Kahuku on Oahu's East Side. This cozy, thoughtfully designed 1-bedroom, 1-bathroom vacation rental offers a perfect blend of comfort and convenience, ideal for families or small...
Ocean-View Comfort at Kihei Garden Estates C204
Welcome to this top-floor loft-style condo offering breathtaking ocean (from the lanai) and garden views in the peaceful South Maui neighborhood. This beautifully upgraded two-bedroom, two-bath unit is perfect for anyone seeking a relaxing Maui getaway. Enjoy the charm...
Waimea Bay Luxury Estate Views & Hot tub
Summary:Immerse yourself in the ultimate Hawaiian experience at Waimea Bay Luxury Estate, located on a corner bluff lot in the peaceful neighborhood of Pupukea on Oahu's North Shore. This expansive estate boasts breathtaking ocean views from every angle and is just...
Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates
We welcome short term rentals Welcome to this nicely updated two bedroom condo located on the peaceful East side of Kuilima Estates at Turtle Bay. The condo features brand new tile flooring in the living room and kitchen along with new kitchen cabinetry!This unit has a...
Jungle Estate - 3 Cottages, 1.5 Acres and a POOL Sleeps 9
If you are dreaming of your own private tropical getaway for up to nine guests in the verdant landscapes on the east side of Hawaii Island, you've come to the right place! Jungle Estate offers three cottages spread over a 1.5 acre parcel in Hawaiian Paradise Park, just...
Luxury Fairwayfront Estate w/Private Pool, Spa, AC & Stunning Views: Kamilo #217
Nestled within the prestigious Mauna Lani Resort community in Kamuela, Mauna Lani KaMilo #217 offers a serene retreat designed for comfort, connection, and island luxury. This 2,491-square-foot residence blends thoughtful design with modern accessibility features,...
Sandcastles - Anahola Beachfront Estate with Hot Tub & Enclosed Yard
Sandcastles TVNCU#1305Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This majestic home, Sandcastles, has vaulted ceilings and large sliding glass doors that open to a spacious...
Charming 2-bedroom Condo with AC & WiFi - Kuilima Estates West
Discover the beauty of Turtle Bay from this delightful 2-bedroom condo. This charming property features 1 king bed, 1 queen bed, 1 sofa bed, and 1 futon, perfect for a tranquil getaway. With one and a half bathrooms equipped with a hair dryers and bathtub, guests can...
Poipu Beach Estates Plantation-Style Home with Pool
Location and convenience to Poipu's best amenities are what make our Poipu Beach Estates home an excellent choice for your Poipu vacation rental.This home is great for large families or a group of people traveling together, with four bedrooms and four bathrooms, it can...
Kuilima Estates West #120: North Shore Golf View
End every day with a stunning Hawaiian sunset on the North Shore of O’ahu when you stay at Kuilima Estates West, unit 120. This newly remodeled 2-bedroom, 2-bathroom with loft townhome is located adjacent to the Turtle Bay Golf course, home of the Fazio and Palmer...
Kapiolani Villa - Luxury Princeville Kauai Estate with Pool
Welcome to Kapiolani Villa, a stunning vacation home perfectly situated near Queens Bath, where luxury meets comfort in a breathtaking setting. With panoramic ocean views from almost every room, this elegant retreat is designed for those seeking the ultimate Kauai...
Welcome to Gorgeous Hideout - Kuilima Estates East
Discover the beauty and tranquility of Kuilima Estates East, nestled on the 17th green of the iconic Turtle Bay Fazio golf course. This beautifully appointed 1-bedroom, 1-bathroom unit spans 658 square feet, offering a perfect blend of comfort and convenience for up to...
Turtle Bay Townhouse Steps to the Beach - Kuilima Estates West
Relax in this beautiful townhouse near Turtle Bay in the exclusive Kuilima Estates West, just a quick walk to several iconic beaches on Oahu’s North Shore. The unit boasts an open kitchen and living area perfect for entertaining family & friends while living the laid...
Hualalai Hainoa Estate | Private Residence | Pool | Panoramic Ocean Views
Spectacular sunset and panoramic view highlight this large estate home with private heated pool and spa at Hualalai Resort. Located along the first fairway of the Tom Weiskopf-designed member's golf course, the home features 4 bedrooms and 4.5 bath on one level, with...
Surfer Hale - Kuilima Estates East # 1
TA/155037900801-01Short Term License STR#2034Kuilima Estates East57-120 Lalo Kuilima #1Beautiful downstairs end unit condo. Step into old Hawaii. Hawaiian decor with natural wood and rattan furniture and tropical colors. 2021 brought new floors, quartz countertops in...
Pulelehua Kuilima Estates West #142: Bright & Lively w/ Community Pool & A/C
A restful retreat on the North Shore of O’ahu, Pulelehua Kuilima Estates West #142 welcomes couples or small families to a ground-floor condo surrounded by lush gardens and fairway views. Located within the iconic Turtle Bay Resort community, this one-bedroom vacation...
Kuilima Estates East #164: Mountain View Condo w/Shared Pool, AC & Near Beach
Live the ultimate paradise experience on Oahu's renowned North Shore at Kuilima Estates East, unit 164. Experience this cozy one-bedroom, two-bathroom townhome that overlooks the stunning Turtle Bay Golf Course. Boasting an unobstructed view of the 18th hole on Fazio's...
Beautiful Turtle Bay Condo - Kuilima Estates East
Beautiful Kuilima Estates at Turtle Bay – We’re an outstanding value priced condo located on 840 acres of landscaped gated grounds, the only tropical resort on Oahu's tranquil and iconic North Shore!Get away from crowded vacation spots with our one-bedroom condo...
Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates.
This charming property has been kept the same since the original build to keep the "sugar plantation" style of the old Hawaii days. No major upgrades have been made to keep an old Hawaii days feel. The RATES REFLECT the style accordingly. This home is perfect for...
Turtle Bay Heliconia - Kuilima Estates East
Beautiful, updated one bedroom, two bath ground floor condo with tile floors throughout. Newly updated extended living room. Updated well appointed kitchen with modern appliances blending in nicely with the open, tastefully decorated living room with large HD TV ....
Maile Retreat ~ Peaceful Home - Kuilima Estates West
This spacious two-bedroom, two bathroom ground floor unit home is your home away from home. Large open living room/dining room is ready to come home to after a long day exploring the beaches or restaurants of the North Shore. Watch the sunrise from your screened in...
Hale Keaka: Luxury Modern Estate w/ Pool, Outdoor Showers, Hot Tub & Ocean Views
This newly built 6-bedroom luxury retreat invites guests to experience Kaua‘i’s south shore in modern, ocean-view elegance. Set within the prestigious Kukui‘ula community in Koloa, Hale Keaka at Kukui‘ula blends architectural sophistication with relaxed island...
Expansive Mauna Lani Resort Estate with Pool, Garden, Maid Service & Beach Access!
This 5 Bedroom, 4.5 bathroom sprawling family compound located in the prestigious Champion Ridge gated community just a short mile drive to the private Beach Club and oceanside restaurant. This spectacular home is surrounded by lush gardens and features a gigantic...
Hale Makai ~ Gold Coast Comfort - Kuilima Estates West
Welcome to Hale Makai ~ Gold Coast Comfort, your idyllic retreat nestled in the heart of Kahuku, Hawaii. This charming 2-bedroom, 2-full bathroom, and 1-half bathroom vacation rental offers a perfect blend of comfort and style, accommodating up to 4 guests. Step inside...
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,...
North Shore Turtle Bay Condo - Kuilima Estates East
750 sq ft ground one bedroom condominium with a full kitchen and glass top stove. A full bathroom, screened in lanai looking out over Turtle Golf Course, open living area with a flat screen TV and couch. This peaceful and private space is located on the grounds of the...
Private Townhouse on the North Shore - Kuilima Estates West #131
The perfect mixture of resort life in a private home. This spacious 3 bedroom, 2 bath townhome is located adjacent to the Turtle Bay Resort and its two golf courses, the Fazio and Palmer Courses. This unit is located in the Kuilima Estates, which provides access to the...
Multi-Dwelling, Private Estate with Ocean Views and Two Hot Tubs TVNC#4284
Welcome to Kauai's magical North Shore!!! This 3 acre property with house and guest house offers pristine privacy and ocean views with a private path to a secluded beach. Kauai Vacation Hideaway also nurtures dozens of fruit trees that guests can pick from. Located just...
North Shore Getaway @ Turtle Bay - Kuilima Estates East
AWESOME NORTH SHORE GETAWAY @ TURTLE BAY! Short walk to ocean and safe family-friendly beach.Welcome to our air conditioned and spacious condo at Kuilima Estates East, located right at the entrance of Turtle Bay, Ritz Carlton North Shore. Our 1 bedroom condo with loft...
Kailua Beach Estate: Historic Property with Large Yard & Ocean View
Recent Updates: Newly constructed upstairs deck, Brand new window ac unit in master bedroom, new patio furniture, new sectional couch in living room. Our beach estate is located on over an acre of land, just one house back (a quick 30 second walk down a sandy beach...
Hale Nene: 5 BR Keauhou Estates Home with Pool & Ocean View
Summary:Aloha! Welcome to Hale Nene.The Space:This elegant, one-of-a-kind Hawaiian estate within the exclusive gated community of Keauhou Estates features its own private pool and relax in a warm spa tub with gentle water flow. Maximum occupancy strictly enforced in...
North Shore Country Estate - 17 Acres, Great Views
*30 day rental. Please Inquire. DescriptionThe North Shore Country Estate is one of a kind 5-bedroom, 4-bath in a 3500 square foot home on 17 acres, in the sleepy North Shore Oahu town of Kahuku. You and your party of up to 12 people will enjoy this beautifully designed...
Hot Deal! Ilima West Kuilima Estates #18 by Gather Near to Golf Course
Welcome to Ilima West Kuilima Estates #18 at Turtle Bay by Gather, a bright and inviting one-bedroom townhome with a loft that sleeps up to five guests. Nestled on Oahu’s fabled North Shore, this 658-square-foot retreat fronts the 1st hole of the Fazio Golf Course,...
Aloha Ku'ilima - Kuilima Estates West
Experience the ultimate North Shore escape at Aloha Kuilima, a chic retreat just minutes from The Ritz-Carlton at Turtle Bay. This 1 bedroom, 2.5 bathroom haven features a private screened in lanai and two heated pools on property with charcoal BBQ grills. Enjoy modern...
Kihei Garden Estates - Condo on the Beach of Maui
This Maui condo is located in the heart of Kihei Hawaii called Kihei Garden Estates, located within 300 feet of the ocean and 20 minutes from the Kahului Airport. Modern amenities, the condo is perfect for a family of 4 adults and 2 children being two stories. Includes...
One Bedroom/Two Bathroom Ground Floor Condo - Kuilima Estates East
One Bedroom/Two Bathroom Ground Floor Condo Sleeps 4From the moment you drive into this gated complex you will feel the peace and tranquility of Turtle Bay. As you walk through the door of this Hawaiiana tropical style decorated one bedroom/two bathroom, ground floor...
Poipu Beach Estates: Walk to Beach/Shops, Sleeps 8-16, AC, Pool, Fitness Club!
Aloha! Welcome to Hawai'i!This amazing Balinese style home with 4 master bedrooms each with its attached bathroom is the perfect way to explore beautiful Kauai. Nestled on a one acre lot surrounded by tropical gardens at Poipu Beach Estates, this home is in the heart of...
Kailua-Kona Estate – Luxury Mansion
Welcome to the largest home* on the Big Island! Highlights include the 100' infinity edge pool, new outdoor pickleball court, 16+ person movie room, and a ~2000 sqft great room.“The place is out of this world beautiful.” – Anca, 5-Star Review“The view...
Incredible Kekaha Beachfront Estate for 10!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Main Home: This custom home is on a ocean front estate. It has three bedrooms and three bathrooms. The home has large sliding doors that disappear into the walls so you won't know where...
Sea Breeze Retreat at Turtle Bay - Kuilima Estates West
Aloha and welcome to our Sea Breeze retreat, a 2-bedroom, 2.5-bath condo at Turtle Bay! Step outside the living room onto a beautifully manicured lawn overlooking the Fazio Golf Course. This gated condo offers the perfect blend of relaxation and convenience, just a...
Ku'ulei @Turtle Bay - Pool, AC, Beach - Kuilima Estates West
Looking for a resort-style getaway that truly has it all? You’ve found it! This beautifully appointed retreat offers breathtaking sunset views, stylish new furnishings, and a fully equipped kitchen—plus a host of thoughtful amenities to make your stay unforgettable....
Kihei Garden Estates G-102 | Steps to the Beach!
Indulge in the ultimate Maui experience at our charming one-bedroom, one-bath ground-floor condominium in Kihei, Hawaii. Just steps away from the beach, Kihei Garden Estates G-102 offers a serene oasis amidst breathtaking ocean views and stunning sunsets.Relax on the...