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.
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...
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...
Beautiful Kuilima East Estates Townhome - Golf Course/Ocean Views
Breezy View: Your Ideal Hawaiian GetawayWelcome to Breezy View, the perfect retreat for your Hawaiian vacation. This spacious end unit features 1 bedroom, 2 bathrooms, and an additional loft space, comfortably accommodating up to four guests. Situated towards the back...
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...
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....
Turtle Bay 1br/1 bath condo - Kuilima Estates West
NUC #: 90/TVU-0268 - TMK 5-7-001:029-0195 or 57001029 - TAX IDs: TA-213-950-4640-01 & GE-213-950-4640-01Turtle Bay 1br/1 bath condo. Just relisted after a 2 year hiatus. Tile floors throughout, full size futon, 42” HD TV, Roku, wifi. Adequate sized living room, kitchen,...
Hale Kauka ~ House of the Artist - Kuilima Estates East
Welcome to Hale Kauka, an exquisite Artist's Retreat nestled on the prestigious Fazio Golf Course at The Ritz-Carlton, Turtle Bay. This enchanting one-bedroom, two-bathroom haven offers a serene escape for up to four guests. The master bedroom features a plush king bed,...
Turtle Bay Sea Shells - Kuilima Estates West
Ground Floor Unit. (Stairs from parking lot and down into unit.) Really cute unit with Hawaiian décor and tasteful artwork. Window Air Conditioning in both bedroom and living room keeps the unit cool and comfortable. Comfortable California king bed. 42" flat-screen TV....
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...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Hale Nani ~ Beautiful Hawaiian Home - Kuilima Estates East
Welcome to Hale Nani, a spacious family retreat nestled in the serene Turtle Bay on Oahu's East Side. This charming 1-bedroom, 2-bathroom with loft vacation rental offers a perfect blend of comfort and luxury, ideal for families or groups of friends. The master bedroom...
Turtle Bay Resort 166 - Kuilima Estates West
Turtle Bay Resort 166Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'An ideal tropical getaway awaits at this stylishly remodeled 1BR condo, located on the third hole of the Turtle...
Anini Ohana Estate - Two Spacious Homes near Anini Beach
Anini Ohana Estate-includes the Main and Ohana guest house TVNCU# 4255Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'**Please note this Vacation Home is located in the tsunami...
Turtle Bay Wicked Wahine - Kuilima Estates West
Perfectly located ground floor unit on the 1st tee of the Fazio Course with the Turtle Bay Club House out your back door and beautiful sunset views. The lovely 2 bedroom with a loft and 2 bathroom unit has tile flooring throughout the unit. Walk-in shower upstairs and...
Turtle Bay Paradise Family Beach Getaway - Kuilima Estates West
TA-045-144-4736-01 Legal Rental #1791 TMK#570010290133 ALOHA!!Enjoy Your Tropical Hawaiian Getaway in our Family Friendly Beach Home, Paradise in Turtle Bay! Clean and comfortable, our air conditioned Wi-Fi enabled condo is a Perfect Rejuvenation Beach Escape for...
Turtle Bay Primrose - Kuilima Estates East
Cozy 1 bedroom 2 bathroom ground floor unit with laminate flooring. WIFI. Window A/C located in bedroom, 2 TV's, DVD, screened-in lanai, tropically decorated. Blu-Ray player. Fully equipped kitchen and laundry center. Free parking just outside your door. Wheelchair...
Turtle Bay Condo: Hawaiian Style & Cozy - Kuilima Estates East
Our condo was carefully designed and decorated to provide a cozy, Hawaiian home feel. It is located on the North Shore , Oahu, which is famous for Turtle Bay and it's Kuilima Point. Home to the best of Oahu's beaches, surfing, golfing, horseback riding and more. If you...
Turtle Bay Condo in Kahuku - Kuilima Estates East
Cozy, spacious 1 bedroom+ loft and 2 bathroom upstairs condo. Air conditioning in the bedroom only but great breeze from lanai and beautiful view of golf course. Free WiFi. Tucked away in quiet location close to pool. Two bathrooms, one on the main floor with tub and...
Turtle Bay Sea Breeze - Kuilima Estates East
Affordable, comfortable second story 1 bedroom + loft and 2 bathroom condo. Ceramic tile in the entry, bathrooms, and fully equipped kitchen. Carpet throughout the unit, with a spiral staircase to the loft. Window A/C located in the bedroom only. Free WiFi. Laundry...
Turtle Bay Alea: 2 BR, 2 BA Condo in Kahuku - Kuilima Estates West
Lovely condo, tastefully decorated. Window A/C's in each bedroom with ceiling fans throughout the unit. Updated modern kitchen with granite countertops and bathrooms . Wi-Fi with flat screen TV's in both living room and master bedroom. Queen bed in master bedroom and in...
KBM Resorts | FREE CAR | Kuilima Estates | 2-Bedroom Condo at Turtle Bay! KUL-E113
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Modern Hidden Gem in Turtle Bay Resort - Kuilima Estates East
Welcome to this charming 1-bedroom condo nestled within a serene community, offering a perfect blend of comfort and recreation. With a spacious bedroom with a king size bed and a convenient pull-out couch, this condo comfortably accommodates up to 4 guests. The condo is...
Pu'ukala Sunset Estate w/ Amazing Ocean Views! by RedAwning
Escape to the breathtaking beauty of the Big Island and make your vacationdreams come true in this splendid 3-bedroom, 2-bathroom vacation rental home.Nestled in the heart of Kailua-Kona, this tropical paradise offers an open andspacious interior, complete with all the...
NEW Kuilima Estates | Golf View 2 BR Sleeps 6 | Car Incl. w/ 6+ Nights | KUL-W145 by KBM
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
4BD Ka'Ulu Estate: Hualalai Resort Estate w/ Infinity Pool, Hot Tub & Golf Views
Important Resort Notices• Each December, Hualalai Resort holds its annual Chairman’s Club event.• Each January, Hualalai Resort hosts the Mitsubishi Electric Championship.These events will result in temporary modifications to guest access at select resort amenities....
Mā’ili Blue Estate by Gather: Oceanfront Retreat w/ Beach Access & Sunset Views
Ma'ili Blue Estate is a private oceanfront retreat on Maili Point, where wide coastal views, steady trade winds, and golden sunsets define each day. Set directly along the shoreline on Oahu’s sunny west side, this spacious home blends relaxed island living with...
Mauna Kea Fairways North Estate Luxury Residence
Mauna Kea Fairways Estate Ocean View Luxury ResidenceAbout This PropertySet within the prestigious Mauna Kea Fairways North community, this one-of-a-kind ultra-luxury ~9,500 sq ft estate offers sweeping ocean views, golf course frontage, and seamless access to one of...
Kihei Garden Estates G205 Close to Beach and Stores
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 2 bedroom 2 bath, lofted unit in the heart of Kihei. Wander right out to the well maintained grounds and enjoy...
Diamond Head Beachfront Estate by Gather: Luxury Oceanfront w/ Heated Pool
A private oceanfront retreat in Honolulu’s most exclusive enclave, Diamond Head Beachfront Estate blends contemporary elegance with the rhythm of island life. Set steps from the water’s edge, this six-bedroom residence invites you to slow down, breathe deeply, and...
Oceanview FarmLux Estate | Stargate Farm Retreat
Welcome to Stargate Farm — a FarmLux oceanview estate on 18 private acres in North Kohala. This brand-new sanctuary blends luxury living with the living land, offering ocean views, vaulted wood ceilings, Turkish travertine, granite-slab showers, and three serene king...
Portlock Oceanfront Estate: Luxe Beachfront Villa w/ Pool & Ocean Views
Wake up to sweeping ocean views and the sound of waves just beyond your lawn at Maunalua Estate, a private beachfront holiday home set along one of Honolulu’s most coveted stretches of sand. With views spanning Koko Head to Diamond Head and the city skyline, this...
Rare Private Gated Estate on Kamaole I Beach – Maui’s Premier Swimming Beach
Something special is coming to Hale Maui No Ka Oi.A curated refresh is in its final stages; new furnishings, refined finishes, and elevated décor selected to honor the home's warmth while bringing a new level of polish to every room. The kind of details you notice the...
Pristine North Shore Nine Bedroom Estate Overlooking The Pacific Ocean
Cocooned within twenty acres of pristine Hawaiian land on Maui's North Shore, this exclusive nine-bedroom estate exists as a peaceful gateway to the past—a private sanctuary that captures a century of stories and a singular moment in time. Lush tropical canopy surrounds...
Luxury Hawaiian Oceanfront Estate
Welcome to where Oceanfront Luxury and World-Class Culinary Excellence Converge. Perched dramatically above Hawaii's famed Hamakua Coast, Waterfalling Estate is a rare fusion of architectural magnificence, natural wonder, and curated luxury.This iconic...
Tantalus Glass House: 3BR Hillside Estate w/ Panoramic Views
Hovering above Honolulu in a canopy of green, Tantalus Glass House (3 BD) is a striking architectural estate where glass, steel, and sky converge. From sunrise over the Pacific to city lights shimmering at night, this 5,953-square-foot hillside residence delivers...
Summer Starts Here Sale! Turtle Bay's Kuilima Estates West #104
Located at the entrance of the magnificent Ritz Carlton at Turtle Bay, this property is just steps away from the spectacular coastline of Oahu’s tranquil North Shore. About an hour from downtown Honolulu, enjoy the peace and quiet of this unit on your next dream...
Kauikeolani Estate, Experience Kaua'i’s Historic Heart, Hanalei, TVNC #1092
Tucked away in the lush valley of Hanalei, Kauikeolani Estate is a rare and historic treasure that captures the essence of Old Hawai'i. Once home to prominent island residents Albert and Emma Wilcox, this storied estate stands today as both a luxurious retreat and a...
Palekaiko Estate Luxurious Ocean View 2 Masters Pool
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...
Nene Cottage on Pali'uli Estate by an active Volcano
Nēnē Cottage is a one bedroom one bathroom cottage with an inviting patio off the back. You can enjoy the sights of this small farm from the patio. Listen to 'io, Hawaiian hawks, as they soar overhead. This is very rare and amazing to see. We have wild pheasants, turkey...
Diamond Head Sea Pool House: Oceanfront Estate w/ Private Sea Pool
Black Point Ocean Villa rests above the Pacific in Diamond Head’s coveted Black Point enclave, offering rare oceanfront privacy, architectural character, and seamless access to Black Point Pool, a private gated community sea pool carved into the coastline. Elevated over...
Hale Laule'a at Kukui'ula by Gather: 5BR Luxury Estate w/ Pool & Views
Set within the prestigious Kukui'ula community in Koloa, Hale Laule'a at Kukui'ula is a contemporary island retreat offering five bedrooms, seven baths, and accommodations for up to 11 guests. Overlooking manicured golf fairways with mountain and ocean views beyond,...
Mauna Lani 5BD Lux Estate (OE12) at One Ocean | Pool, Spa & Golf Views
5BD Mauna Lani Luxury Ocean Estate (OE12) is a newly completed, single-level compound within the private, gated One Ocean enclave at Mauna Lani Resort. Completed in late 2025 and designed for privacy and flow, the home’s contemporary architecture opens to golf course...
Oceanview Air-Conditioned Kona Estate w/ Infinity Pool & Sunset Views
Set within the gated enclave of Keauhou Estates, Hale Nai'a is a striking oceanview retreat where architecture, art, and horizon-wide vistas take center stage. From its dramatic entry to the infinity-edge pool overlooking Keauhou Bay, this private home delivers a...
Hapuna Estates 10 Four Bedroom
Designed for elevated island living, this gorgeous and expansive retreat showcases impressive common areas that are ideal for relaxing and entertaining, with open-concept living spaces that flow seamlessly to the outdoors. Guests will enjoy effortless indoor-outdoor...
Diamond Head Luxe Private Estate with Pool | Sleeps 11
Diamond Head Luxe is a refined private estate in Honolulu’s coveted Diamond Head neighborhood, nestled at the end of a private road, and designed for effortless island living at scale. With generous interiors, seamless indoor-outdoor flow, and a resort-style pool...
Hahalua Bay Villa by Gather: Luxury Oceanfront Estate w/ Pool & Views
Stay in a villa featured on Netflix’s hit series Temptation Island—now reimagined as your own private tropical retreat.Hahalua Bay Villa, also known as Manta Ray Bay Villa, is an iconic oceanfront estate set directly on the shoreline of Keauhou Bay in Kailua-Kona....
Pali’uli Estate has an old Hawaiian country feel in a tropical rain forest.
Our bed and breakfast was built in 1930-1938. The name on the entrance pillar is Pali-uli. This meaning found in the Hawaiian dictionary is very accurate. n. A legendary land of plenty and joy, said to be on Hawaii, where chiefs' children were raised. Lit., green cliff....
Private Hibiscus Hale on Gorgeous Gated Estate + Walk to the Beach
Please message for reservation inquiries for any dates. Calendar is not accurate. Mahalo!Private North Shore Guesthouse on Gated Acre | Walk to Beach + SurfRelax at this tranquil North Shore Oʻahu getaway, located on a gated, private estate of approximately one full...
The waterfall estate at Maunaolu
The Ultimate Hawaiian Estate RetreatWelcome to your own private Hawaiian oasis—an expansive 4-bedroom, 4-bathroom luxury estate set on over an acre of lush, landscaped grounds. Perfect for family gatherings, retreats, and unforgettable getaways, this resort-style...
NEW! Kuilima Estates | KBM Resorts | 2 Units, 4 Bedrooms | ML-2750
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...