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Luxury Vacation Rentals in Hawaii

Indulge in the ultimate Hawaiian escape with our handpicked collection of luxury vacation rental properties across the islands. Whether you're seeking an elegant oceanfront estate, a secluded mountain retreat, or a resort-style villa with world-class amenities, we have the perfect home for your dream getaway. Explore our most exclusive listings on each island: discover stunning Oahu luxury villas, breathtaking Maui luxury estates, serene Kauai beachfront homes, and extraordinary Big Island vacation retreats. Each property is carefully selected for its comfort, style, and unforgettable views. Whether planning a family celebration, honeymoon, or wellness escape, you’ll find island elegance at its finest. Browse more exclusive villas below and start planning your luxury Hawaii experience today!

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Luxurious Beachfront Vacation Home in Kauai
Luxurious Beachfront Vacation Home in Kauai
Luxurious Beachfront Vacation Home in Kauai

Luxurious Beachfront Vacation Home in Kauai

Experience this unique Hawaiian dream home situated on over an acre of lush tropical beachfront landscaping. Spanning approximately 5,000 sq ft, this gated property offers unparalleled privacy and comfort. Walk down the sandy beach just steps from your door, or enjoy the stunning ocean views from the hot tub or seating area at night.

  • 3 bedroom
  • 5 bathroom
  • Sleeps 6
Hawaii> Kekaha
from $1,887 
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Remodeled Maui Condo Near Beach with Pool & Hot Tub
Remodeled Maui Condo Near Beach with Pool & Hot Tub
Remodeled Maui Condo Near Beach with Pool & Hot Tub

Remodeled Maui Condo Near Beach with Pool & Hot Tub

Welcome to Kihei Garden Estates C-105, your perfect Maui retreat! This beautifully remodeled ground-floor condo offers a seamless blend of modern comfort and island charm, just steps from a stunning Maui beach.
The space has been thoughtfully updated with stylish furnishings, polished concrete floors, and contemporary counters, creating an inviting and elegant atmosphere.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kihei
from $231 
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Immaculate maintained Turtle Bay Condo - Kuilima Estates West
Immaculate maintained Turtle Bay Condo - Kuilima Estates West
Immaculate maintained Turtle Bay Condo - Kuilima Estates West

Immaculate maintained Turtle Bay Condo - Kuilima Estates West

Welcome to your perfect North Shore getaway! This bright, surf-inspired condo offers a clean, comfortable space equipped with modern renovations, a full kitchen, and cozy bedrooms. Located in the Turtle Bay area, it's just a five-minute walk to stunning beaches renowned for world-class surfing, snorkeling, fishing, and swimming for all ages.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $908 
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Turtle Bay Penthouse 164 - Kuilima Estates West
Turtle Bay Penthouse 164 - Kuilima Estates West
Turtle Bay Penthouse 164 - Kuilima Estates West

Turtle Bay Penthouse 164 - Kuilima Estates West

Experience the perfect Hawaiian getaway at this charming ground-floor condo within the Kuilima Collection at Turtle Bay Resort. This spacious one-bedroom unit offers stunning panoramic views of the golf course and lush mountains, creating a serene tropical oasis.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kahuku
from $474 
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Elegant 2BR Ocean View Guest House in Kona
Elegant 2BR Ocean View Guest House in Kona
Elegant 2BR Ocean View Guest House in Kona

Elegant 2BR Ocean View Guest House in Kona

Experience a beautifully furnished 2-bedroom, two-bath guest house on a gated estate with stunning ocean views. The residence features antique accents, an open beam ceiling, and over 1000 square feet of living space, plus a 280-square-foot lanai ideal for outdoor relaxation.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 7
Hawaii> Kailua-Kona
from $288 
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North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West
North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West
North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West

North Shore Renovated 2 Bedroom + Loft & Pool - Kuilima Estates West

Welcome to our spacious and beautifully renovated North Shore Turtle Bay Resort condo, offering 2 bedrooms, a versatile loft, and 2 bathrooms. The condo features large King beds in both bedrooms, a Queen and Twin in the loft, and a pull-out Queen sofa bed in the living room, accommodating families or groups comfortably.

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kahuku
from $1,105 
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Turtle Bay Hale Lani - Kuilima Estates East
Turtle Bay Hale Lani - Kuilima Estates East
Turtle Bay Hale Lani - Kuilima Estates East

Turtle Bay Hale Lani - Kuilima Estates East

Welcome to your perfect Hawaiian getaway at Kuilima Estates, nestled on the renowned Turtle Bay grounds. This modern, upgraded 1-bedroom condo with a loft and a half bath offers a blend of comfort and stunning scenery.
The unit features a contemporary kitchen with new cabinets, appliances, and granite countertops, making meal prep a delight.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $470 
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Spacious 5-Bedroom Home with Pool & Ocean Access in Kauai
Spacious 5-Bedroom Home with Pool & Ocean Access in Kauai
Spacious 5-Bedroom Home with Pool & Ocean Access in Kauai

Spacious 5-Bedroom Home with Pool & Ocean Access in Kauai

Experience the vibrant charm of this beautifully designed 5-bedroom home nestled on Kauai's North Shore. With a cheerful, tastefully decorated interior, each room boasts its own unique character, harmonized by aquamarine color accents, hardwood details, and inspiring decor.

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Princeville
from $1,306 
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Charming Kona Cottage with Tropical Garden & Amenities
Charming Kona Cottage with Tropical Garden & Amenities
Charming Kona Cottage with Tropical Garden & Amenities

Charming Kona Cottage with Tropical Garden & Amenities

A charming 1930s-era cottage nestled on the grounds of a historic Kona home offers a perfect blend of comfort and natural beauty. The cottage features a screened-in lanai sitting area, ideal for relaxing or dining outdoors amidst lush tropical landscaping.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Holualoa
from $254 
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Turtle Bay Condo - Kuilima Estates East
Turtle Bay Condo - Kuilima Estates East
Turtle Bay Condo - Kuilima Estates East

Turtle Bay Condo - Kuilima Estates East

Welcome to your perfect North Shore retreat on the legendary island of Oahu! This legally permitted second-story condo offers a comfortable and stylish stay with stunning views of the Turtle Bay Golf Course's 18th hole from the large lanai. Designed to accommodate 2 to 6 guests, the condo features a spacious bedroom with a queen bed, a loft with two queen beds and a half bath, and a full bathroom with a tub.

  • 2 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $850 
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Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West
Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West
Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West

Two bedroom: Steps away from Turtle Bay Resort, AC - Kuilima Estates West

Discover this charming Turtle Bay townhouse, perfectly positioned near the North Shore's top attractions. The two-level, end-unit condo offers privacy and comfort, with a spacious loft and a cozy bedroom. Step onto the outdoor lanai to enjoy scenic views of the golf course while sipping a drink or having a meal.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $456 
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Poipu Golf Course Suite with Ocean Views
Poipu Golf Course Suite with Ocean Views
Poipu Golf Course Suite with Ocean Views

Poipu Golf Course Suite with Ocean Views

This newly renovated, air-conditioned suite offers a luxurious getaway in the heart of Poipu’s exclusive neighborhood on Kauai's sunny South Shore. Surrounded by lush golf course greens, the property provides an open, airy atmosphere with breathtaking views from your private lanai.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Koloa
from $396 
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Hale Makai at Diamond Head – Oceanfront Estate
Hale Makai at Diamond Head – Oceanfront Estate
Hale Makai at Diamond Head – Oceanfront Estate

Hale Makai at Diamond Head – Oceanfront Estate

Experience the beauty and tranquility of O'ahu at Hale Makai, a stunning oceanfront vacation home with breathtaking views of Diamond Head Crater. Located on the Gold Coast, this property offers a perfect blend of luxury, privacy, and convenience, less than 3 miles from the vibrant Waikiki area.

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $2,000 
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Keauhou Bay Oceanfront Estate
Keauhou Bay Oceanfront Estate
Keauhou Bay Oceanfront Estate

Keauhou Bay Oceanfront Estate

Experience a spectacular oceanfront lifestyle at this luxurious estate overlooking Keauhou Bay. The home features soaring vaulted ceilings throughout the living areas and into the grand master suite, creating an airy, open atmosphere. The beautifully landscaped yard fronts the bay, providing a serene backdrop for your stay.

  • 8 bedroom
  • 7 bathroom
  • Sleeps 14
Hawaii> Kailua-Kona
from $4,451 
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Amazing Turtle Bay Condo - Kuilima Estates East
Amazing Turtle Bay Condo - Kuilima Estates East
Amazing Turtle Bay Condo - Kuilima Estates East

Amazing Turtle Bay Condo - Kuilima Estates East

Welcome to your perfect Hawaiian escape in Turtle Bay! This updated 1-bedroom condo with a loft comfortably sleeps 4-5 guests and offers a blend of modern comfort and tropical charm. Located on the upper level at Kuilima Estates East, this corner unit boasts wonderful ocean breezes and is conveniently close to parking and the pool.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $473 
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Turtle Bay - Relax In Paradise - Kuilima Estates West
Turtle Bay - Relax In Paradise - Kuilima Estates West
Turtle Bay - Relax In Paradise - Kuilima Estates West

Turtle Bay - Relax In Paradise - Kuilima Estates West

Welcome to your ideal Hawaiian getaway at my well-maintained condo located at 57-101 Kuilima Drive, Kahuku. This welcoming unit offers a clean, comfortable space with a variety of amenities designed to enhance your stay. Guests will find tennis rackets, bodyboards, snorkel and mask sets, beach towels, and chairs at their disposal, making it easy to enjoy outdoor activities.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kahuku
from $317 
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Townhome at Kuilima Estates at Turtle Bay
Townhome at Kuilima Estates at Turtle Bay
Townhome at Kuilima Estates at Turtle Bay

Townhome at Kuilima Estates at Turtle Bay

Welcome to this spacious second-story townhome at Kuilima Estates at Turtle Bay, ideally situated on the eastern side for quick access to the stunning Turtle Bay beach. This condo features a fully renovated interior with contemporary touches, ensuring a comfortable and stylish stay.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $749 
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Sandcastles Kauai Beach House with Lanai & Garden
Sandcastles Kauai Beach House with Lanai & Garden
Sandcastles Kauai Beach House with Lanai & Garden

Sandcastles Kauai Beach House with Lanai & Garden

Welcome to Sandcastles, a stunning beachfront home nestled on the East Shore of Kauai in Anahola. This spacious residence features soaring vaulted ceilings and large sliding glass doors that open to a expansive lanai, perfect for lounging or dining al fresco.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Anahola
from $1,400 
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Breezy View: Hawaiian Golf Course Retreat with Ocean Views
Breezy View: Hawaiian Golf Course Retreat with Ocean Views
Breezy View: Hawaiian Golf Course Retreat with Ocean Views

Breezy View: Hawaiian Golf Course Retreat with Ocean Views

Breezy View offers an ideal Hawaiian escape with stunning views and modern comforts. This spacious end-unit features 1 bedroom, 2 bathrooms, and a loft, comfortably accommodating up to four guests. Nestled towards the back of the Kuilima Estates East complex, it boasts direct frontage on the 10th hole of the George Fazio course at Turtle Bay Resort, providing a spectacular backdrop for your vacation.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $374 
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Luxury Ocean View Villa with Pool & Jacuzzi
Luxury Ocean View Villa with Pool & Jacuzzi
Luxury Ocean View Villa with Pool & Jacuzzi

Luxury Ocean View Villa with Pool & Jacuzzi

Experience the ultimate island retreat in this stunning ocean view villa with luxurious amenities and breathtaking vistas. The main floor boasts a large lanai with a sparkling pool, soothing jacuzzi, outdoor dining area, and a cozy fire pit lounge.

  • 5 bedroom
  • 5 bathroom
  • Sleeps 16
Hawaii> Kailua-Kona
from $1,175 
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Luxury Kailani Villa with Ocean Views Hawaii
Luxury Kailani Villa with Ocean Views Hawaii
Luxury Kailani Villa with Ocean Views Hawaii

Luxury Kailani Villa with Ocean Views Hawaii

5-acre estate with unobstructed 180-degree views of the Pacific Ocean. Nestled near Ninole on the east coast of the Big Island, this luxurious single-story home is an ideal base for exploring the island's top attractions like Volcanoes National Park, Hilo, and the Hawaii Tropical Botanical Garden.

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Ninole
from $574 
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Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East

Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East

Immerse yourself in the beauty of Oahu at this beautifully renovated 1-bedroom condo located on the lush grounds of Turtle Bay Resort. The unit offers stunning panoramic views of the Arnold Palmer golf course and the surrounding mountains, creating a serene and picturesque setting for your vacation.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kahuku
from $471 
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A beautiful Turtle Bay condo on the golf course - Kuilima Estates East
A beautiful Turtle Bay condo on the golf course - Kuilima Estates East
A beautiful Turtle Bay condo on the golf course - Kuilima Estates East

A beautiful Turtle Bay condo on the golf course - Kuilima Estates East

Welcome to your dream vacation home on the North Shore of Oahu. This beautifully maintained Turtle Bay condo offers a perfect blend of comfort and convenience. Inside, you'll find a private master bedroom equipped with a king-sized bed and air conditioning, providing a cool retreat after a day exploring the island.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $482 
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Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates

Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates

Welcome to your perfect North Shore getaway at Turtle Bay Estates West, part of the exclusive Kuilima Collection by Hawaii Life Vacations. \nThroughout your stay, enjoy modern upgrades including remodeled kitchens and bathrooms completed in 2020, and brand-new A/C units installed in October 2024 for ultimate comfort.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $751 
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Magical Maui Oceanfront Paradise with Turtles & Dining
Magical Maui Oceanfront Paradise with Turtles & Dining
Magical Maui Oceanfront Paradise with Turtles & Dining

Magical Maui Oceanfront Paradise with Turtles & Dining

Welcome to the most magical place on Maui! This stunning oceanfront property offers breathtaking views of the Pacific Ocean, where you can snorkel alongside graceful turtles just steps from your lanai. Watch surfers riding the waves and enjoy exquisite direct oceanfront dining that captures the essence of a tropical paradise.

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Lahaina
from $3,448 
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Luxury Hawaiian Estate with Ocean & Mountain Views
Luxury Hawaiian Estate with Ocean & Mountain Views
Luxury Hawaiian Estate with Ocean & Mountain Views

Luxury Hawaiian Estate with Ocean & Mountain Views

Welcome to The Ko'olau Plantation Estate, your ideal Hawaiian hideaway nestled on five lush acres at the start of Oahu's North Shore. This exquisite property offers over 60,000 square feet of outdoor space, including a spacious front lawn perfect for gatherings and celebrations.

  • 9 bedroom
  • 9 bathroom
  • Sleeps 14
Hawaii> Kaaawa
from $3,342 
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Luxury Kailua Villa Near Beach with Lagoon Pool
Luxury Kailua Villa Near Beach with Lagoon Pool
Luxury Kailua Villa Near Beach with Lagoon Pool

Luxury Kailua Villa Near Beach with Lagoon Pool

A lush tropical paradise awaits you at this gated estate just steps from Kailua Beach, offering a luxurious mini resort experience. 5M upgrade, Palione Papalani (Hawaiian for "Heavenly Sands") is an impressive 6-bedroom estate set amid exotic gardens and a serene lagoon-style pool with a hot tub.

  • 6 bedroom
  • 6 bathroom
  • Sleeps 16
Hawaii> Kailua
from $3,089 
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Hawi Ocean View Estate with Private Gardens
Hawi Ocean View Estate with Private Gardens
Hawi Ocean View Estate with Private Gardens

Hawi Ocean View Estate with Private Gardens

Come stay and relax at this stunning quartzite stone-sided custom home nestled on a 10-acre private estate in historic Hawi on the Big Island of Hawaii. Built with love and attention to detail by the owners, this home is perfect for family gatherings and friends' reunions.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Hawi
from $570 
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Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West
Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West
Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West

Comfortable Condo on Turtle Bay Golf Course Sleeps 5 - Kuilima Estates West

Discover this beautifully maintained condo located on the North Shore of Oahu at Turtle Bay Resort. Situated on the Championship Fazio Golf Course, this 1-bedroom plus loft offers a luxurious and comfortable Hawaiian retreat. The property boasts brand new furniture, beds, linens, granite countertops, and stainless steel appliances, creating a modern and inviting atmosphere.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Kahuku
from $629 
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Private Townhouse on the North Shore - Kuilima Estates West #131
Private Townhouse on the North Shore - Kuilima Estates West #131
Private Townhouse on the North Shore - Kuilima Estates West #131

Private Townhouse on the North Shore - Kuilima Estates West #131

The perfect blend of resort luxury and private comfort, this spacious 3-bedroom, 2-bath townhome is ideally situated near Turtle Bay Resort and its renowned golf courses, Fazio and Palmer. Located in the Kuilima Estates, residents enjoy access to the community pool and tennis or pickleball courts, making it an excellent choice for active families and leisure seekers alike.

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Kahuku
from $637 
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Hale La’i Luxury Vacation Home on Big Island
Hale La’i Luxury Vacation Home on Big Island
Hale La’i Luxury Vacation Home on Big Island

Hale La’i Luxury Vacation Home on Big Island

Welcome to Hale La’i, a serene and elegant Hawaiian-style retreat nestled on the slopes of Hualalai at 800 feet elevation. This private luxury home offers breathtaking views of the Pacific Ocean and Kailua Bay, providing an ideal setting for relaxation and family gatherings.

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Kailua Kona
from $1,245 
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Hale Laule'a Banyan Bed & Breakfast Suite Hawaii
Hale Laule'a Banyan Bed & Breakfast Suite Hawaii
Hale Laule'a Banyan Bed & Breakfast Suite Hawaii

Hale Laule'a Banyan Bed & Breakfast Suite Hawaii

The Hale Laule'a Banyan Suite offers a luxurious escape on Hawaii's Hamaku'a Coast, combining privacy, comfort, and natural beauty. Situated on a sprawling 5-acre estate, this private, gated suite provides an authentic Hawaiian experience with modern amenities.

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Hakalau
from $202 
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Hale Kai Sunset Estate – Private Beachfront Paradise
Hale Kai Sunset Estate – Private Beachfront Paradise
Hale Kai Sunset Estate – Private Beachfront Paradise

Hale Kai Sunset Estate – Private Beachfront Paradise

Welcome to Hale Kai Sunset Estate, a stunning private retreat located on the North Shore of Oahu. Nestled behind a secure, gated entrance, this luxurious beachfront property offers unmatched privacy and spectacular ocean views, making it the perfect escape for families, couples, or groups seeking a unique Hawaiian experience.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Haleiwa
from $2,026 
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Luxury Kona Vacation Home with Ocean Views
Luxury Kona Vacation Home with Ocean Views
Luxury Kona Vacation Home with Ocean Views

Luxury Kona Vacation Home with Ocean Views

Aloha and welcome to Honu Hale by Gather, your luxurious Hawaiian retreat in Kona. 5-bathroom estate comfortably hosts up to 16 guests, making it perfect for family reunions, gatherings, or a dream vacation. Situated in an upscale neighborhood just 2 miles from popular beaches like Magic Sand Beach and Kahaluu Beach Park, Honu Hale offers unparalleled access to Kona’s top attractions.

  • 7 bedroom
  • 4 bathroom
  • Sleeps 16
Hawaii> Kailua Kona
from $1,771 
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Ohi'a Kona Estates Hawaiian Retreat with Ocean Views
Ohi'a Kona Estates Hawaiian Retreat with Ocean Views
Ohi'a Kona Estates Hawaiian Retreat with Ocean Views

Ohi'a Kona Estates Hawaiian Retreat with Ocean Views

Discover the perfect Hawaiian escape at Ohi'a Kona Estates, a serene retreat nestled in the hills above Kona. This estate offers four spacious one-bedroom suites, each featuring a king bed, private bath, living area, and modern amenities. Guests enjoy stunning views of the Pacific Ocean, cool breezes, and a temperate climate, making it ideal for relaxation and exploration.

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Kailua-Kona
from $1,286 
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Oahu North Shore Vacation Home @ Kuilima Estates West
Oahu North Shore Vacation Home @ Kuilima Estates West
Oahu North Shore Vacation Home @ Kuilima Estates West

Oahu North Shore Vacation Home @ Kuilima Estates West

Welcome to this elegant Hawaiian home situated on Oahu's North Shore, offering a perfect blend of comfort and style. This spacious 3-bedroom, 2-bathroom residence has been meticulously renovated to provide modern amenities and a luxurious atmosphere.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $786 
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Luxury North Shore Waimea Bay Estate with Ocean Views
Luxury North Shore Waimea Bay Estate with Ocean Views
Luxury North Shore Waimea Bay Estate with Ocean Views

Luxury North Shore Waimea Bay Estate with Ocean Views

Immerse yourself in the ultimate Hawaiian getaway at Waimea Bay Luxury Estate, located on a tranquil corner bluff in Pupukea on Oahu's North Shore. This expansive property features a luxurious main house and an adorable guest cottage, accommodating up to 20 guests, making it ideal for families, groups, or corporate retreats.

  • 9 bedroom
  • 6 bathroom
  • Sleeps 20
Hawaii> Haleiwa
from $2,436 
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Ocean View Cottage in Hawi, Big Island Hawaii
Ocean View Cottage in Hawi, Big Island Hawaii
Ocean View Cottage in Hawi, Big Island Hawaii

Ocean View Cottage in Hawi, Big Island Hawaii

This charming, custom-built cottage offers stunning ocean views and is nestled on a lush 10-acre private estate in Hawi, Big Island. Spanning 1000 square feet, it comfortably sleeps up to four guests, with a bedroom and a loft, each furnished with a cozy queen bed.

  • 3 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Hawi
from $277 
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Luxury Beachfront Estate on North Shore Oahu
Luxury Beachfront Estate on North Shore Oahu
Luxury Beachfront Estate on North Shore Oahu

Luxury Beachfront Estate on North Shore Oahu

A rare opportunity to stay in paradise on the North Shore of Oahu. This luxurious beachfront estate offers panoramic ocean views, direct beach access, and year-round sunsets. Designed for larger families or groups, the home features five bedrooms and four bathrooms, providing ample space for up to 10 guests.

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Haleiwa
from $1,440 
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Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates
Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates
Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates

Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates

Welcome to this beautifully updated two-bedroom condo nestled on the peaceful east side of Kuilima Estates at Turtle Bay. This inviting unit features modern touches like new tile flooring in the living room and kitchen, along with fresh kitchen cabinetry.

  • 2 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> East Kahuku
from $445 
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Hawaii Jungle Estate: Private Cottages & Pool
Hawaii Jungle Estate: Private Cottages & Pool
Hawaii Jungle Estate: Private Cottages & Pool

Hawaii Jungle Estate: Private Cottages & Pool

5 acres in Hawaiian Paradise Park, just south of Hilo. This private retreat comfortably accommodates up to nine guests, making it ideal for families or friends traveling together.
Jungle Villa is the main highlight—a luxurious one-bedroom cottage with a private yard surrounded by areca palms and vibrant flowering trees like the Royal Poinciana.

  • 5 bedroom
  • 4 bathroom
  • Sleeps 9
Hawaii> Keaau
from $595 
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Mauna Lani KaMilo #217 - Luxury Island Retreat
Mauna Lani KaMilo #217 - Luxury Island Retreat
Mauna Lani KaMilo #217 - Luxury Island Retreat

Mauna Lani KaMilo #217 - Luxury Island Retreat

Welcome to Mauna Lani KaMilo #217 by Gather, a charming four-bedroom, three-bathroom home nestled in the prestigious Mauna Lani Resort on the stunning Kohala Coast of Kamuela, HI. This property is now offering extended stays at reduced rates, making it an ideal choice for those seeking a longer tropical escape.

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Kamuela
from $1,386 
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Luxury Oceanfront Estate in Poipu with Pool
Luxury Oceanfront Estate in Poipu with Pool
Luxury Oceanfront Estate in Poipu with Pool

Luxury Oceanfront Estate in Poipu with Pool

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 (named for the waves crashing against lava-rock cliffs) offers all the irresistible features you’d expect in a tropical paradise, and more.

  • 3 bedroom
  • 4 bathroom
  • Sleeps 6
Hawaii> Koloa
from $2,537 
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Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)
Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)
Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)

Kuilima Estates West - remodeled 2 bedroom ( 2nd bedroom is large loft)

Discover this beautifully remodeled 2-bedroom condo in Kuilima Estates West, Oahu. The second bedroom is a spacious loft, perfect for relaxing after a day at the beach. The property features two full bathrooms, ensuring comfort for all guests. Located next to Turtle Bay Resort but independently managed, this condo offers a peaceful retreat with access to three swimming pools, tennis courts, and miles of scenic walking paths amid lush greenery.

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Kahuku
from $558 
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Luxurious Hualalai Estate with Pool and Ocean Views
Luxurious Hualalai Estate with Pool and Ocean Views
Luxurious Hualalai Estate with Pool and Ocean Views

Luxurious Hualalai Estate with Pool and Ocean Views

Experience the ultimate Hawaiian retreat in this spectacular estate at Hualalai Resort. 5 bathrooms, each with luxurious en-suite facilities, including dual vanities, bathtubs, and outdoor garden showers. The primary suite offers ocean vistas, a king bed, smart TV, and direct access to a lanai, creating a perfect sanctuary.

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Kailua-Kona
from $4,028 
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Surfer Hale - Kuilima Estates East # 1
Surfer Hale - Kuilima Estates East # 1
Surfer Hale - Kuilima Estates East # 1

Surfer Hale - Kuilima Estates East # 1

Experience the laid-back charm of this beautiful downstairs end unit at Kuilima Estates East, located near Turtle Bay on Oahu's North Shore. The condo features authentic Hawaiian decor with natural wood and rattan furniture, complemented by tropical colors that evoke the island's spirit.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Kahuku
from $371 
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Charming North Shore Oahu Condo Near Turtle Bay
Charming North Shore Oahu Condo Near Turtle Bay
Charming North Shore Oahu Condo Near Turtle Bay

Charming North Shore Oahu Condo Near Turtle Bay

Escape to a tranquil retreat on the North Shore of Oahu with this charming one-bedroom, one-bathground floor condo at Pulelehua Kuilima Estates West #142. Nestled within the scenic Turtle Bay Resort grounds, this home offers a perfect blend of comfort and island charm.

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $425 
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Charming Haleiwa 3-Bedroom Vacation Estate
Charming Haleiwa 3-Bedroom Vacation Estate
Charming Haleiwa 3-Bedroom Vacation Estate

Charming Haleiwa 3-Bedroom Vacation Estate

Escape to Haleiwa and enjoy a stunning 3-bedroom estate designed for comfort and relaxation. This property features two queen beds and one king bed, making it ideal for families or groups seeking a peaceful retreat. Guests can unwind in the bathtub after a day exploring the island, stay connected with WiFi, and use amenities like a hair dryer for added convenience.

  • 3 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Haleiwa
from $789 
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Kukuna Estate – Luxury Kailua-Kona Coast Villa
Kukuna Estate – Luxury Kailua-Kona Coast Villa
Kukuna Estate – Luxury Kailua-Kona Coast Villa

Kukuna Estate – Luxury Kailua-Kona Coast Villa

Discover the exquisite Kukuna Estate, a serene and luxurious retreat perched at 1300 feet above sea level on Hawaii's renowned Kona Coast. This elegant villa offers breathtaking panoramic views of the Pacific Ocean and pristine beaches from its spacious living areas and multiple lanais.

  • 7 bedroom
  • 7 bathroom
  • Sleeps 14
Hawaii> Kailua-Kona
from $6,253 
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Beautiful Turtle Bay Condo - Kuilima Estates East
Beautiful Turtle Bay Condo - Kuilima Estates East
Beautiful Turtle Bay Condo - Kuilima Estates East

Beautiful Turtle Bay Condo - Kuilima Estates East

Aloha! Discover the stunning Turtle Bay and Kuilima Estates, nestled on 840 acres of lush, landscaped grounds on Oahu's North Shore. This beautifully decorated one-bedroom condo offers the perfect Hawaiian getaway, combining comfort and convenience in a tranquil setting away from crowded tourist spots.

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Kahuku
from $396 
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