1. Hawaii Vacation Rentals » Hawaii Luxury Properties

Hawaii Luxury Properties for Rent

Discover the pinnacle of island living with our curated collection of Hawaii luxury properties for rent. From secluded beachfront estates in Anahola to modern architectural marvels near Diamond Head, each property offers a unique blend of elegance and comfort. Enjoy amenities such as private pools, gourmet kitchens, and expansive lanais, all set against the backdrop of Hawaii's stunning landscapes. Whether you're seeking a romantic retreat or a spacious haven for family gatherings, our luxury rentals provide the perfect setting for an unforgettable Hawaiian escape.​

Experience the allure of Hawaii's diverse islands, from the lush greenery of Kauai to the vibrant shores of Oahu. Our luxury properties place you within reach of pristine beaches, world-class golf courses, and exquisite dining options. Embrace the spirit of aloha and create lasting memories in a paradise that feels like your own private sanctuary.

Large Gated Oceanfront Estate ~ Secluded on a beach, safe all year TVNC-4185

Hale Aloha… On The Sand TVNC-4185
Anaik Martin, is the property manager, lives nearby and is available 24 hours a day, 7 days a week, (808) 652-3410. Professionally cleaned and disinfected by a licensed

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Anahola
from $2,979 
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PRIVATE, GATED ESTATE steps away from the beach - and paradise!

Make unforgettable memories in this secluded, polynesian-styled beachfront estate situated on the eastern side of Oahu next door to the famous Magnum PI Robin's nest. Flanked by the majestic Ko’olau mountains on one side and a reef-protected

  • 3 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Waimanalo
from $1,455 
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Hilo's most secluded luxurious ocean front estate

Welcome to one of Hawaii’s most secluded luxurious ocean front estates! Our family vacation home is situated on a 16 acre heart of palm plantation and is located on the Scenic Route, just minutes from downtown Hilo.


Upon entering

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Papaikou
from $737 
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Beachfront Family Estate. Great for multiple families.

Located in central Kihei, nestled on the northern end of beautiful Halama Street. Family-owned and operated legal short-term rental. There are two dwellings on this beach front property - an apartment building with four units and a detached 2

  • 6 bedroom
  • 4 bathroom
  • Sleeps 15
Hawaii> Kihei
from $2,547 
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Four Bedroom Oceanfront Estate at Naupaka Place at Waikoloa Beach!

Welcome to Pacific Sunset Villa, home of expansive ocean views and ultimate luxury. This award winning home with 4 bedroom with ensuite bathrooms and 3 half bathrooms sits on an oceanfront setting and offers easy access to all the amenities at

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Waikoloa
from $5,782 
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This magnificent, island-style estate truly exceeds all expectations.

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

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Waimea
from $1,319 
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Hululani Luxury Estate, A/C, Pool and Spectacular Ocean Views

This serene estate is named Hululani, or "Heavenly," for its pristine beauty. This truly fabulous home has awesome, panoramic views of the mountains, Bali Hai and Hanalei Bay from virtually every room as well as from the private, saline swimming

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Princeville
from $1,358 
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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

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $6,623 
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Beautiful & Spacious upstairs Apt in Poipu Beach Estates! One Bedroom with A/C!

This beautiful upstairs 1 bedroom Ohana is located in Poipu Beach Estates just minutes from all sunny Poipu has to offer. A perfect retreat for a couple looking to find a comfortable place to stay in a charming setting. The bedroom has a Queen

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Koloa
from $361 
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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

  • 5 bedroom
  • 5 bathroom
  • Sleeps 14
Hawaii> Koloa
from $1,460 
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Luxury Oceanview Private Estate Pool & Hot Tub In Kaanapali-Rainbow Hale Maui

Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali – a Family Retreat or Private Honeymoon Get -away. Surrounded by 5 acres of Maui tropical plantation, lies a spectacular estate like you've always dreamed of, with the lifestyle

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Lahaina
from $1,654 
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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

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Captain Cook
from $1,374 
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Kona coffee estate in Holualoa

Kona Coffee Estate Guest Apartment with Ocean and Garden Views

Our estate is situated on the slopes of Mt. Hualalai on the Big Island of Hawaii. We are located just 15 minutes from the Kona Airport, 10 minutes from the quaint coastal town

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Holualoa
from $274 
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Maka Nui Estate private family resort style home.

Aloha,

And welcome to Maka Nui! The name means Big view which you will see when you enter the gate to our paradise. The home sits on a cliff overlooking an undeveloped and historic coastline including Kealakekua Bay and Pu'uhonua o'

  • 6 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $1,549 
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Pole House On Wooded Estate With Fabulous Coastline And Mountain Views

As of April 1, 2020, our guesthouse is now only available as a long term rental (6 month/180 days or more).

Our guesthouse is nestled along the slopes of Mount Hualalai on our 40 acre ranch and coffee estate. Located above the historic

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Holualoa
from $272 
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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

  • 7 bedroom
  • 6 bathroom
  • Sleeps 18
Hawaii> Waimea
from $3,912 
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Hale Maluhia Estate at Poipu By Parrish Kauai- elite home w/ AC & heated pool!

Enjoy the luxury and comfort of our newest Elite home centrally located in Poipu Beach Estates. This custom home takes full advantage of many views and is also positioned to enjoy the fabulous trade wind breezes. The spacious and open great room

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Poipu
from $2,020 
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Private Ocean View Estate in Poipu with A/C, Jacuzzi, & Pool 5 min walk to beach

Ho'ohu Nani has Four Bedrooms (2 Master Suites), Den with Fold-Out Couch, Four Full Bathrooms, and Two Half Baths. Ocean Views from Upstairs Living Area and Covered Lanai. The Kitchen includes top-of-the line appliances with a new Wolf

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Koloa
from $1,685 
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Serene PUAKO BEACHFRONT ESTATE. All Oceanview bedrooms, Large courtyard Pool.

Stately and serene, THE HOME OF THE HULA MOON is one of the most beautiful contemporary oceanfront properties in PUAKO. Each bedroom has a perfect ocean view. Located near the end of the road, you will enjoy year-round sunsets and privacy.

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Puako
from $2,511 
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Pickleball, basketball, Ocean Views! 6br/4.5ba,pool,hot tub, Gated Estate!

Pacific View is nestled in the majestic West Maui Mountains, a vast area of lush valleys and cliffs. This lovely 5-acre estate is uniquely situated to capture all of the beautiful west Maui offers.

Pacific View is a gated villa offering a

  • 6 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Lahaina
from $4,265 
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Luxury 5 BR Estate over Beach w/ Huge Views, Pool, Hot Tub - TVNC#4201

Welcome to Hale Mana, one of Kauai's most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views.

If you are

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kilauea
from $4,574 
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Mango Sunsets: Gorgeous Oceanview Estate w/Private Pool, Spa & AC

We invite you to sit back, relax and experience the dazzling sunsets, tropical breezes and never ending ocean views from "Mango Sunsets", our private 3-acre Kohala Ranch estate where modern elegance meets traditional quality craftsmanship. This

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kamuela
from $878 
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Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a

***Please note there is a 7-night minimum during the holidays. Christmas reservations must check out by 10 AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14-night minimum to book both Christmas

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kailua Kona
from $976 
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Waiulu Golf & Oceanview Estate Hualalai

Welcome to the exquisite Waiulu Estate Villa at Four Seasons Hualalai Resort. This estate offers a private and serene setting with close wide-open ocean views. The estate has been recently updated with new contemporary décor by the renowned

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $7,904 
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Dolphin House Oceanfront Estate

STVR 19-363225 - NUC 19-1616

Picture 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

  • 5 bedroom
  • 5 bathroom
  • Sleeps 11
Hawaii> Kailua Kona
from $1,913 
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Gorgeous Oceanfront Estate, Steps From Beach w/AC & Puako Bay Views: 10D

Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time.

This oceanfront Kohala Coast home with breathtaking coastline views offers the ultimate setting for a

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kamuela
from $1,738 
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Probably The Most Peaceful & Beautiful of North Shore Estate

Greetings! Welcome to the - HaleAlohaEstate - on Oahu's North Shore. Come experience a truly authentic Hawaiian experience in our beautiful Estate home with 6+ bedrooms, and 4.5 bathrooms on the quiet – best part of Oahu’s famous North

  • 6 bedroom
  • 5 bathroom
  • Sleeps 20
Hawaii> Waialua
from $1,570 
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Newly Renovated Stunning Beachfront 5 Bed, 6.5 Bath Estate with Pool, Spa & AC

One of the most stunning homes and locations in Maui. The beachfront home is 'U' shaped, with a spacious lanai area which includes a pool and spa and which overlooks the beach, ocean, and the island of Lanai. Located on a private palm tree

  • 5 bedroom
  • 7 bathroom
  • Sleeps 10
Hawaii> Lahaina
from $3,969 
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Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!

“Notice: In compliance with the Revised Ordinances of the City and County of Honolulu, the Property will be made available for your use and occupancy for a period of thirty (30) days.”

$79.00 Admin Fee is for our Damage Protection

  • 9 bedroom
  • 8 bathroom
  • Sleeps 20
Hawaii> Waimanalo
from $10,723 
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Kuilima Estates West 3 Bedroom

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

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $560 
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Ocean Front Estate, *Private Pool*, Exclusive Beach Frontage

Live the dream at this oceanfront gem, with wide beach frontage and an inviting courtyard pool that beckons you to experience the ultimate Hawaiian retreat in style. Kick off your shoes and step barefoot off your expansive covered lanai onto a

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Waimea
from $1,683 
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Charming Holualoa Ranching-Era Estate near Kailua and Keauhou. Away from it all!

Gracious comforts of yesteryears and featured in the coffee table book, The Hawaiian House Now, the home is an historic 1895 structure, modified in the 1940s. Retaining the charm of old Hawaii with architecture and furnishings of the day, while

  • 4 bedroom
  • 3 bathroom
  • Sleeps 11
Hawaii> Holualoa
from $805 
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23 Acre Estate, Ocean and Sunset Views, Hot Tub, Private Beach Access, Jungle!


GE/TA 125-285-3760-01
TA#W90869281-01
Permits: TVNC 4272 SP2012-10

Welcome to Jungle Bee!

Note: Pricing includes both homes on the property and exclusive use of the estate.

Jungle Bee Farms is a stunning 23 acre

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kilauea
from $1,971 
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Stunning Kaimupulehu Grand Estate Hualalai

This “Over-the-Top” estate is a resort within a resort! Guests often choose to Opt Out of paying the resort fees and enjoy this quiet retreat without the hustle and bustle of the resort activity. Beautiful infinity pool with sandy

  • 5 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kailua-Kona
from $6,758 
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Kuilima West Estates 198B

Surf's up on the North Shore and our condo is the perfect place to Hang Ten! You'll appreciate the attention to detail, modern amenities and the chic, decor when you escape to our Surfer's Paradise. Our location provides easy access to the

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $851 
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Cottage on Beachfront Estate property, central Hanalei Bay

This amazing and completely refurbished home is situated on a stunningly beautiful one-acre, gated OCEANFRONT estate property, right in the middle of magical Hanalei Bay. It is, in fact, one of the ONLY vacation rental cottages on beachfront

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Hanalei
from $934 
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Gather with Family or Friends at a Gorgeous Estate. Pool, Views - Permitted

Maui County Rental permit - STPH 2014/0004
TA-097-868-8000-01 / GE-097-868-8000-01
TMK-270031100000
Welcome to Seaview! This is a unique family style vacation home, offering space for up to ten family members or friends to vacation

  • 5 bedroom
  • 5 bathroom
  • Sleeps 10
Hawaii> Haiku-Pauwela
from $1,841 
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ALOHA SANDS LUXURY BEACH FRONT ESTATE, PUAKO. HOLIDAYS DEC. 1-28 REOPENED!

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

  • 4 bedroom
  • 5 bathroom
  • Sleeps 11
Hawaii> Kamuela
from $3,358 
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Mauna Kea Villa 3037 - Architectural Island Estate

Villas at Mauna Kea #37 FREE resort access to both the Mauna Kea Beach Hotel and The Westin Hapuna Beach Resort For many years, the Mauna Kea Resort has served the world's most sophisticated travelers. It has been their special place to visit,

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Waimea
from $1,600 
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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

  • 6 bedroom
  • 5 bathroom
  • Sleeps 14
Hawaii> Laie
from $2,880 
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Charming Historical Home - Crutchfield Estate

This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $1,602 
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SPRING BREAK SPECIAL! Lau'eki Estate ~ Hualalai ~ Sweeping Views ~ Infinity pool

Welcome to your tranquil oasis at the exclusive Lalani Lau'eki Estate at the Four Seasons Hualalai Resort. This private estate is nestled between exquisite and expansive ocean and Hualalai mountain views—perfect for beautiful Hawaiian

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua Kona
from $5,241 
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Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles

Our home was updated during the last half of 2021 and in early 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

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Lahaina
from $1,981 
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The Bluffs 22: Opulent Oceanview Luxe Estate w/ Pool/Spa, AC & Views

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

  • 4 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Kamuela
from $5,030 
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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

  • 3 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Kihei
from $1,347 
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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

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Kailua-Kona
from $986 
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Private Hawaiian Estate in Mauna Kea Resort

Set in a gated community, this oceanfront estate has been crafted by Hawaii’s best architects and interior designers and is a true masterpiece. This residence offers a great room with sliding glass pocket doors for indoor/outdoor island

  • 5 bedroom
  • 10 bathroom
  • Sleeps 10
Hawaii> Waimea
from $8,463 
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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

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $923 
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Serene Pakui Pua Estate ~ Hualalai ~ Secluded~Saltwater Pool~Personal Concierge

Welcome to your very own paradise at Hualalai Four Seasons Resort! One of three unique residences in the prime Kauhale neighborhood with easy and quick access to the Four Seasons Resort amenities. This home is located at the end of Pakui Street

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua-Kona
from $4,280 
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Hale Koolau Estate - AC, Hot Tub TVNC #1017/1018

Hale Koolau Estate (Main House + Treehouse), Haena
Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018
Transient vacation rental is located in the tsunami evacuation zone

On the north shore of Kauai, Hale

  • 4 bedroom
  • 4 bathroom
  • Sleeps 14
Hawaii> Haena
from $1,773 
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