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 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...
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...
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...
Luxury 3br Poipu Estates Home w Private Pool
This home is a true Poipu gem. Located in the Poipu Beach Estates neighborhood, this home features a spacious open floor plan with a covered lanai. The kitchen flows seamlessly into the living area creating the perfect place to gather and “talk story.” All of the...
Kahakai Estates Hale: Posh Gold Coast Home w/ Pool, Spa, AC & Sunset Views
Kahakai Estates Hale by Gather – Newly Renovated Luxury Vacation Rental in Kailua-Kona, Big IslandLocation: Kahakai Estates, Kailua-Kona | Sleeps: 6 | Bedrooms: 3 | Bathrooms: 2.5 | Central A/C | Private Pool & Hot TubEscape to paradise in this fully remodeled,...
Stunning Estate Property In Gated Community Steps From The Ocean
Welcome to our 5 star rated vacation home. We call our home Forever Sunsets because with just a short walk to the water in our gated community you can watch the sunset every night. You are also a short 600 yard walk to Magic Sands Beach, the most popular sandy beach in...
Oasis at Turtle Bay Condo on the North Shore - Kuilima Estates West
This homey one bedroom (cal king bed) with upstairs loft (with one queen and one twin bed)/two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to five! It's close to the public beach at the Turtle Bay hotel, sitting on the 1st hole of PGA Fazio...
Oceanfront Estate, Steps to Ocean - Pool, Spa, Home Theater, B-Ball Court!
The 'Blue Wave' house is a one-of-a-kind oceanfront resort home located in the Kolea community that was completely upgraded in 2020. This beautiful 4 bedroom home was custom built to make every dream of an oceanfront paradise come true - with a private pool deck and hot...
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...
Tropical Turtle Bay Condo - Kuilima Estates East
This newly listed unit features a loft bedroom, with a large kitchen and living room. Unit is located right on the Arnold Palmer golf course and a 5 minute walk or 2 minute drive from Turtle Bay Resort. Enjoy luxury gated community amenities featuring gated access,...
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...
One of a kind private Luxury beachfront Estate with oceanfront pool & jacuzz
TVNC #4224This is truly a one of a kind Hawaiian dream home. Stroll down the sand beach and find Hawaiian Paradise set on over an acre of beautiful tropical beachfront landscaping. This approx 5000 sq ft gated home has all the comforts one could need from a gourmet...
Lalamilo Beach House – Oceanfront Estate at Beach 69 with Guest Cottage
The much loved and well appointed Lalamilo Beach House is ideally located on the north end of Waialea Bay (Beach 69) which is known for its beautiful white sand beach and turquoise blue water.Three bedrooms in the main house each have their own private bathroom and you...
Kihei Garden Estates C-105 - Stunning Renovation, AC, Steps from the Beach!
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.------------------------------------Welcome to Kihei Garden Estates C-105, where...
Immaculate maintained Turtle Bay Condo - Kuilima Estates West
ALOHA! Perfect North Shore getaway! This surf inspired condo is bright and clean, and stocked with all you should need for a great stay! Located in the Turtle Bay Area, it's very close to beaches (about a 5 minute walk), golf coarse, and some amazing restaurants. This...
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...
Guest house on gated acre estate, Sleeps up to 7; Great for Events, too
Beautiful, elegantly furnished and fully-equipped 2 bedroom, two bath guest house, with antiques and open beam ceiling, on a 1 acre gated estate, with koi pond, waterfall, fountain, chlorine-free pool and hot tub, and 180 degree ocean-view lanai. Fully furnished and...
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...
North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West
Aloha and welcome to our spacious and beautifully renovated North Shore Turtle Bay Resort 2 Bedroom condo that includes an additional 3rd loft room + 2 bathrooms. Directly outside the living room is a large manicured grassy lawn and the Fazio Golf Course. This gated...
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,...
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...
Delightful Artful Bungalow on Historic Estate Property. Choice Holualoa!
A charming 1930-era cottage, with a screened-in sitting area on the lanai, well-stocked kitchen, bath, will sleep two in a comfy queen-sized bed. Perfect for single or double occupancy. Covered parking close by. An outdoor patio fronting the cottage lanai, is a private...
Turtle Bay Condo - Kuilima Estates East
This is a legal vacation rental located on the Legendary North Shore of Oahu!Permit #: 2211-CCH-0353TA #: TA-106-244-7616-01GE #: GE-106-244-7616-01Property TMK: 570010270159Famous North Shore Beaches, Two beautiful Swimming pools, Free Parking, No Resort Fees, AC,...
Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West
Enjoy the North Shore by staying close to everything when you stay at this centrally-located place. The townhouse is right next to the famous Turtle Bay Resort. Legal Short Rental: STR 2755.Our two-level, one-bedroom plus loft, end unit condo is located on the second...
Oahu North Shore Vacation Home @ Kuilima Estates West
Welcome to your elegant Hawaiian home, a spacious retreat offering resort-style living on Oahu’s North Shore. This stunning 3-bedroom, 2-bathroom property comfortably accommodates up to 6 guests, making it perfect for families or groups of friends. Step inside to find...
Beautiful Private Cottage w/ AC in Sunny Poipu Beach Estates 5 Minutes to Beach!
This new, air-conditioned suite is in an exclusive neighborhood of Poipu, offering you the most rare and impressive accommodation the sunny South Shore has to offer. The rolling golf course greens that surround this property provide an open and airy feel. Enjoy the...
Lovely, spacious private estate, 300 ft to Sunset Beach TA#083767910401
30 DAY RENTAL*****A beautiful, peaceful, private north shore estate, 300 ft from sunset beach. The main house has 4 bedrooms and 4 bathrooms and sleeps 8 in beds. You may rent the cottage for an additional 2 people-check availability-it's called the plantation cottage;...
Hale Makai at Diamond Head – Oceanfront Estate
Ideally positioned along Honolulu’s prestigious Gold Coast with Diamond Head Crater as its backdrop, Hale Makai at Diamond Head is a licensed nightly oceanfront rental (NUC 90/TVU-0390) offering luxury, privacy, and the rhythm of true island life—just three miles...
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront Home
This property is professionally-managed by Private Homes Hawaii, LLC and is a licensed short-term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1774 for the main house and 1990/NUC-1775 for the guest cottage. It is compliant with Hawaii State Legislation...
Hale O Ka Nalu Po'i: Oceanfront Estate on Poipu Coastline
Breathtaking, magnificent, superlative, sublime: there’s simply no way to overstate the extraordinary appeal of this uniquely situated, strikingly beautiful oceanfront estate. Hale O Ka Nalu Po'i (poetically named for the waves that crash dramatically against...
Turtle Bay - Relax In Paradise - Kuilima Estates West
Aloha ! Welcome to my condo located at 57-101 Kuilima Dr. Kahuku Hawaii 96712. My condo is clean, well maintained, and comes with many amenities . Some amenities are Tennis rackets, bodyboards, snorkel and mask sets , beach towels, beach chairs, and more. Full access to...
Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)
***WE ARE ON OAHU, AND CONTINUE TO WELCOME VISITORS***Fully remodeled 2 bedroom ( 2nd bedroom is large loft) beautiful condo with 2 full bathrooms. We are in Kuilima Estates West, which is next to , but not a part of, the Turtle Bay resort. We have 3 pools for your use....
Townhome at Kuilima Estates at Turtle Bay
Welcome to this spacious second story townhome at Kuilima Estates at Turtle Bay. This condo is located on the eastern side of Kuilima Estates, making this condo one of the closest units to the Turtle Bay beach. .With a completely updated interior, guests enter into the...
Panoramic Ocean Views! Luxury Estate - Pool, Hot Tub, Jacuzzi & Air Conditioning
On the main floor of the home, there is a large lanai with a pool, jacuzzi, outdoor eating area and a fire pit with lounge area. Inside, on the main floor, you will find a **newly renovated** kitchen, large eating area, living room area, and the mother-in-law suite. The...
6.5 acres Oceanfront Estate with180-degree views of the deep blue Pacific Ocean!
Kailani Villa is the epitome of privacy, comfort and style and far away from the fray of normal life. The six-and-one-half acre estate is beautifully landscaped and offers unobstructed 180-degree views of the deep blue Pacific Ocean. Retreat to the immense oceanfront...
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Kuilima Collection | 101 EastPanoramic Golf Course Views | Renovated 1-Bedroom Corner UnitEscape to the lush North Shore of Oʻahu and experience the best of Turtle Bay living at Kuilima Collection | 101 East. Nestled along the 17th hole of the famed Arnold Palmer Golf...
A beautiful Turtle Bay condo on the golf course - Kuilima Estates East
Welcome to paradise, enjoy this North Shore Turtle Bay condo. Brand new state of the art air conditioner in master bedroom, living room, and loft. Private master bedroom with A/C and king sized bed and bathroom. Upstairs find two queen size beds in a loft and fan. This...
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
Wish You Were Here – Turtle Bay Condo | Stylish, Spacious + Steps to your next Adventure..Escape to Oahu’s legendary North Shore and stay in this beautifully updated 2-bedroom, 2-bath ground-floor condo at Turtle Bay Resort, with a bonus loft and room for the whole...