Luxury Vacation Rentals in Hawaii Kai, Oahu

Hawaii Kai is an upscale residential community on Oahu’s southeastern coast, offering a quiet and scenic alternative to the busier areas of Honolulu. Nestled between the coastline and lush ridges, this peaceful neighborhood is just a short drive from world-famous Hanauma Bay, where visitors can snorkel among vibrant coral reefs and tropical marine life. It’s also home to the challenging Koko Head Crater hike-one of Oahu’s most rewarding trails with sweeping views from the summit.

Vacation rentals in Hawaii Kai range from modern condos to luxurious private homes, many with marina frontage, ocean views, and high-end amenities like pools, lanais, and spacious living areas. Nearby Maunalua Bay is perfect for paddleboarding, kayaking, and boating. Guests enjoy the balance of a relaxed residential atmosphere with easy access to city attractions - Waikiki is just a 20-minute drive away, offering shopping, dining, nightlife, and beaches.

Whether you're planning a quiet retreat or an active vacation near the island’s top natural and urban destinations, Hawaii Kai delivers comfort, beauty, and convenience. Browse our listings to find your ideal vacation rental in one of Oahu’s most desirable coastal communities.

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Family-Sized Tranquil Farmhouse Retreat. Event Space. Nearby Shopping Complex

*This property may not be rented for less than 30 consecutive days. Prices will be adjusted on the number of days occupied Special arrangements please reach out. Please contact us directly for event requests.

Are you traveling to O’ahu with your family and looking for the perfect place to call home?
Registration Number: 390050600000, GE-012-439-3984-01, TA-012-439-3984-01

• 4 bedroom
• 2 bathroom
• Sleeps 10

Hawaii> Honolulu

from $428 

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Luxurious 4-Bedroom Ocean View Retreat in Hawaii Kai

Welcome to your dream getaway in the vibrant Hawaii Kai neighborhood! This luxurious, newly renovated 4-bedroom, 3-bathroom home offers a perfect mix of modern comfort and breathtaking natural beauty. Inside, the spacious open-concept living area features high-end finishes, contemporary decor, and large windows that flood the space with natural light.
Registration Number: 390801160000, GE-165-444-6592-01, TA-165-444-6592-01

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $377 

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Luxury Oceanfront Vacation Home in Hawaii Kai

This extraordinary property offers a luxurious oceanfront experience in the renowned Hawaii Kai neighborhood, situated on a rare double-sized ocean lot in Portlock. Designed for large groups seeking privacy and comfort, the estate features multiple structures nestled around a lush tropical courtyard and a sprawling 1,000-square-foot swimming pool.
Registration Number: GE-060-531-3536-01, TA-060-531-3536-01, 390160020000

• 6 bedroom
• 6 bathroom
• Sleeps 12

Hawaii> Honolulu

from $1,407 

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Hale Maluhia Luxury Vacation Home in Oahu

Experience ultimate relaxation and luxurious comfort at Hale Maluhia, a stunning contemporary resort nestled in Hawaii Kai, Oahu. This spacious 4-bedroom home, translating to "house of tranquility," offers nearly 4000 square feet of elegant living space with custom hardwood floors, high ceilings, and expansive windows that invite natural light and ocean breezes.
Registration Number: TA-025-225-0112-01, GE-025-225-0112-01, 391010920000

• 5 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Honolulu

from $1,036 

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Stylish Hawaii Kai Condo with Pool and Patio

Discover this stylish and serene condo located in the desirable Hawaii Kai area of east Honolulu. Recently redesigned, the condo offers contemporary furnishings, a spacious open-plan living and dining area, and two comfortable bedrooms. The highlight is the private outdoor patio equipped with a table and chairs, perfect for enjoying Hawaii's warm weather and fresh air.
Registration Number: 1390080680063, TA-181-932-1856-01, GE-181-932-1856-01

• 2 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $162 

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Waterfront Hawaii Rental at Ohana Kai

This stunning waterfront property at Ohana Kai offers the perfect blend of comfort and scenic beauty in Hawaii Kai. Situated within a secure gated community along Hawaii Kai’s picturesque waterway, this condo provides breathtaking marina and Koko Head views from every room, creating a tranquil and luxurious retreat.

Registration Number: 390080100000, GE-177-601-5360-01, TA-177-601-5360-01

• 3 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Honolulu

from $397 

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Luxury Hawaii Kai Marina Home with Sunset Views

This stunning Hawaii Kai residence offers a perfect blend of comfort and convenience for your Hawaiian escape. Nestled in a peaceful neighborhood with direct access to the marina, this home provides a luxurious haven just minutes from top attractions.

Registration Number: TA-042-034-1248-01, GE-042-034-1248-01, 390320580000

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> honolulu

from $264 

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Spacious 2-Bedroom Guest House Near Hanauma Bay

This spacious, beautifully designed guest house offers a perfect retreat for travelers seeking comfort, style, and convenience on Oahu. The property features a fully-equipped attached 2-bedroom + 2-bath home, with an optional one-bedroom setup that reduces the nightly rate by $50, catering to your space preferences.
Registration Number: GE-114-345-1648-01, TA-114-345-1648-01

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $511 

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Beautiful Ocean and Mountain View Cottages in Hawaii Kai

Discover a stunning vacation escape in Hawaii Kai on the east side of Oahu. This charming cottage, built in 2011 with a new suite added in 2018, offers spectacular ocean views from the main cottage and mountain vistas from the master suite. Nestled in lush mountain forests, the property provides a peaceful retreat away from the busy city life, perfect for rejuvenation and relaxation.

Registration Number: 390830520000, GE-060-165-9392-01, TA-060-165-9392-01

• 1 bedroom
• 1 bathroom
• Sleeps 6

Hawaii> Honolulu

from $361 

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Portlock Paradise: Beachfront Luxury in Hawaii Kai

Welcome to Portlock Paradise, an elegant island retreat offering unparalleled beach access and luxurious amenities in Hawaii Kai. This stunning property sits on a spacious, lush oceanfront lot, providing the perfect setting for a memorable Hawaiian getaway.

Registration Number: 390020180000, TA-008-452-3520-01, GE-008-452-3520-01

• 4 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Honolulu

from $707 

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Luxury 5-Bedroom Hawaii Kai Marina Home with Pool

Nani Wai is a stunning 5-bedroom, 4-bathroom gated residence nestled in the upscale neighborhood of Hawaii Kai, offering breathtaking marina views and direct access to the water. This spacious home is designed to comfortably accommodate larger groups, providing ample indoor and outdoor space for relaxation and entertainment.

Registration Number: TA-068-282-1120-01, GE-068-282-1120-01, 390950040000

• 5 bedroom
• 4 bathroom
• Sleeps 13

Hawaii> Honolulu

from $837 

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Luxury 4-Bedroom Villa in Hawaii Kai with Lagoon Access

Welcome to Villa Laule'a, which means peaceful happiness in Hawaiian. This stunning 4-bedroom townhouse is beautifully furnished and fully equipped to provide a luxurious vacation experience. The villa features high-quality linens, towels, and a fabulous kitchen perfect for preparing meals.
Registration Number: TA-124-812-6976-01, GE-124-812-6976-01

• 4 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Honolulu

from $321 

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Spacious Ocean View Family Villa near Beaches

Set on the slopes of Koko Kai, this spacious two-story family-style home offers panoramic ocean views and breathtaking sunsets over Diamond Head. Decorated with a touch of island charm, the villa is ideal for indoor and outdoor living. The large full kitchen, two living areas, and expansive lanais provide ample space for families and friends to relax and enjoy.
Registration Number: TA-137-893-8880-01, GE-137-893-8880-01, 390230800000, 90/TVU-0258

• 3 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Honolulu

from $1,306 

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Luxury Waterfront Home in Hawaii Kai with Private Dock

This stunning single-story waterfront residence in Hawaii Kai offers a perfect blend of comfort and scenic beauty. Inside, you'll find a fully equipped kitchen, spacious living room, and four bedrooms with three bathrooms, all thoughtfully furnished for a relaxing stay.

Registration Number: TA-068-140-0320-01, GE-068-140-0320-01, 390680200000

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $666 

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Mahina Kai Luxury Hawaii Kai Retreat with Views

Welcome to Mahina Kai by Gather, a beautiful tropical retreat nestled in a quiet cul-de-sac in Hawaii Kai. This spacious five-bedroom, three-bathroom home offers breathtaking views of Koko Crater and the deep blue Pacific, creating an ideal setting for relaxing getaways and memorable family gatherings.

Registration Number: TA-178-279-8336-01, GE-178-279-8336-01, 390730320000

• 5 bedroom
• 3 bathroom
• Sleeps 12

Hawaii> Honolulu

from $1,253 

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Waterfront Oahu Kama'aina Home with Views & Amenities

5-bath waterfront home in Oahu. Designed for comfort and relaxation, this home offers breathtaking views from every room, showcasing the marina, ocean, and lush surroundings. The spacious living areas feature large windows and sliding doors that open onto a private lanai, where you can enjoy the gentle trade winds, the soothing sounds of nature, and stunning sunsets with a glass of wine.
Registration Number: 39008004, TA-038-271-2320-01, GE-038-271-2320-01

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $337 

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Stunning Hawaii Kai Home with Private Pool & Views

Experience the ultimate Hawaiian getaway in this spectacular 4-bedroom, 2-bath home nestled on a ridge in the highly sought-after area of Hawaii Kai. The main level offers a spacious open-concept kitchen and dining area, perfect for family gatherings, along with a comfortable living space, a master bedroom with an en-suite bathroom, and a convenient half bathroom off the hallway.
Registration Number: GE-011-442-5856-01, TA-011-442-5856-01, 390750390000

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Honolulu

from $577 

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Hale Maunalua Ocean View Retreat with Pool

Breathtaking ocean views greet you at Hale Maunalua, a stunning 4-bedroom, 4-bath hillside retreat on Oahu’s east side. \n\nInside, enjoy spacious living areas with wall-to-wall windows showcasing panoramic ocean vistas. The main living room features plush sofas and an armchair, perfect for relaxing while soaking in the scenery.
Registration Number: GE-086-598-4512-01, TA-086-598-4512-01, 1390230750000

• 4 bedroom
• 4 bathroom
• Sleeps 10

Hawaii> Honolulu

from $829 

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Kaiwiki Palace: Tropical 3BR Home Near Ocean

Experience the serenity of island living at Kaiwiki Palace, a beautifully decorated 3-bedroom, 2-bath home nestled on a peaceful cul-de-sac just minutes from the ocean. The home offers a relaxed tropical vibe with beach-chic decor throughout, making it an inviting retreat for families or groups seeking a tranquil getaway.

Registration Number: 1390290370000, GE-085-648-1792-02, TA-085-648-1792-02

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $581 

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Seabreeze Hawaii Kai - 30 Night Minimum Stay

Immerse yourself in the tranquility of Seabreeze Hawaii Kai, an inviting home designed for extended stays with a perfect blend of outdoor beauty and modern comfort. The lush tropical garden and charming stone path lead you to a serene backyard featuring a tranquil koi pond, ideal for reading or unwinding amidst nature's splendor.
Registration Number: 390850230000, GE-201-662-2592-02, TA-201-662-2592-01

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $332 

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Holoholo Hale by Gather Waterfront Retreat in Hawaii Kai

Welcome to Holoholo Hale by Gather, your private waterfront retreat nestled in the peaceful community of Hawaii Kai on Oahu's beautiful marina. This recently remodeled, single-level home combines contemporary elegance with island comfort, making it an ideal choice for your Hawaiian vacation.

Registration Number: 390290010000, GE-024-880-1792-01, TA-024-880-1792-01

• 4 bedroom
• 2 bathroom
• Sleeps 9

Hawaii> Honolulu

from $546 

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Hawaii Kai Dream Home with Ocean Views - 30 Night Stay

Enjoy breathtaking panoramic views of Maunalua Bay, Koko Marina, and the Hawaiian coastline from this beautifully situated 4-bedroom, 3-bath home in Honolulu's Hawaii Kai neighborhood. The property is perched on Mariner’s Ridge, offering unobstructed vistas and easy access to the vibrant town center, just a 15-minute walk away.
Registration Number: 390310020045, GE-145-848-8320-01, TA-145-848-8320-01

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $419 

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Marina Front Townhouse with Ocean Views and Private Dock

Discover this premier marina front townhouse featuring stunning ocean views and a private dock equipped with kayaks, paddleboards, and beach chairs, ideal for enjoying the coastal lifestyle. 5-bath home boasts a large master suite overlooking the marina and the Pacific Ocean, with whale-watching mornings and breathtaking sunsets from the marina front patio, complete with a barbeque and string lights.
Registration Number: TA-027-052-6464-01, GE-027-052-6464-01, 39035016

• 4 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Honolulu

from $383 

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Luxury Beachfront Villa in Hawaii Kai

Nanea Kai Villa by Gather is a luxurious four-bedroom, three-and-a-half-bath beachfront estate nestled along the peaceful shores of Hawaii Kai, Hawaii. This exquisite property sits on a spacious private lot with a meticulously manicured lawn leading directly to a sandy beach, offering a tranquil escape just a short drive from Waikiki's vibrant attractions.
Registration Number: TA-026-671-3600-02, GE-026-671-3600-02, 680270240000

• 4 bedroom
• 3 bathroom
• Sleeps 8

Hawaii> Honolulu

from $2,711 

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Moana Vista Waterfront Retreat on Oahu's Shores

Welcome to Moana Vista, your exclusive waterfront haven nestled between Hauula and Punaluu on Oahu's mesmerizing shores. This beachfront paradise boasts a wide array of outdoor amenities, including a beachfront gym, a covered 10-chair gazebo equipped with electricity and lighting, numerous hammocks and patio chairs perfect for relaxing, an outdoor BBQ grill, and three newly-added beachfront hot tubs—one of which is a spacious 7-person spa.
Registration Number: TA-002-506-5984-01, GE-002-506-5984-01

• 4 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Hauula

from $1,313 

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Sea Cliff Chic – Ultra-Luxury Oceanfront Retreat in Portlock

Immerse yourself in the luxury and natural beauty of Sea Cliff Chic, Oahu's newest upscale residence designed by renowned architect Jim McPeak and built by developer Mark Gosselin. This modern take on Hawaii’s iconic Honeyed Jade style offers oversized, grand spaces centered around breathtaking ocean views.

Registration Number: TA-025-422-8480-01, GE-199-064-7808-01, 390260010000

• 6 bedroom
• 6 bathroom
• Sleeps 12

Hawaii> Honolulu

from $11,568 

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Luxury Hale Ola in Portlock with Ocean Views

This exquisite property, Hale Ola by Gather, is a luxurious and private retreat nestled in the prestigious Portlock neighborhood of Oahu. Offering breathtaking views of the ocean, Diamond Head, and surrounding mountains, this secluded haven is perfect for those seeking tranquility and natural beauty.

Registration Number: GE-033-454-6944-01, TA-033-454-6944-01, 390270180000

• 5 bedroom
• 5 bathroom
• Sleeps 12

Hawaii> Honolulu

from $1,143 

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Hawaii Kai Central Location with Private Pool

Located in the heart of Hawaii Kai, this beautifully renovated single-level home offers a perfect blend of comfort and convenience. A short walk takes you to Maunalua Bay Beach Park, ideal for swimming and picnics, while less than a mile away, you'll find grocery stores like Safeway and Costco, along with several dining options.
Registration Number: TA-089-474-5088-01, GE-089-474-5088-01, 390290290000

• 3 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Honolulu

from $275 

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Luxury Oceanfront Architectural Estate in Honolulu

Experience the ultimate luxury in this exclusive oceanfront estate in Honolulu, a true architectural marvel that has hosted icons like Frank Sinatra, Elvis Presley, and Paul McCartney, who composed "Silly Love Songs" here. This 30-day minimum rental offers unparalleled privacy and spectacular 180-degree ocean views, making it ideal for those seeking a unique and memorable getaway.
Registration Number: TA-111-279-1552-01, GE-111-279-1552-01, 390280170000

• 4 bedroom
• 5 bathroom
• Sleeps 10

Hawaii> Honolulu

from $1,488 

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Luxury Villa Luana with Ocean & Mountain Views

Villa Luana is a stunning retreat nestled against a lush Hawaiian mountainside, blending natural beauty with upscale luxury. This elegant home invites you to indulge in comfort, offering sweeping mountain vistas and serene glimpses of the Pacific Ocean.
Registration Number: GE-097-116-5696-02, TA-097-116-5696-02, 39081092

• 4 bedroom
• 3 bathroom
• Sleeps 12

Hawaii> Honolulu

from $465 

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Portlock Hale Oceanfront Retreat with Pool & Views

Experience the ultimate oceanfront escape at Portlock Hale, a stylish retreat nestled in the heart of Portlock, Hawaii Kai. This private residence offers direct access to the breathtaking shores of Maunaloa Bay via its own private staircase, making it ideal for ocean lovers and adventure seekers alike.
Registration Number: 390160090000, GE-072-291-2768-01, TA-072-291-2768-01

• 5 bedroom
• 3 bathroom
• Sleeps 10

Hawaii> Honolulu

from $696 

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Luxury Oceanfront Hale Makana in Hawaii Kai

Experience the ultimate Hawaiian escape at Hale Makana, a luxurious single-level estate located in Hawaii Kai's most sought-after oceanfront neighborhood. This elegant five-bedroom, seven-bathroom property offers a perfect blend of comfort, style, and breathtaking views.
Registration Number: GE-019-591-8336-01, TA-019-591-8336-01, 390270140000

• 5 bedroom
• 7 bathroom
• Sleeps 10

Hawaii> Honolulu

from $1,596 

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Hawaii Kai Condo with Ocean and Mountain Views

Discover this beautifully remodeled condo in Hawaii Kai, offering breathtaking ocean, marina, and mountain vistas. The unit is designer decorated with new flooring, upgraded appliances, and modern kitchen and bathroom finishes. Resort-style amenities include a fitness center, racquetball courts, swimming pools, hot tubs, BBQ areas, manicured landscaping, recreation facilities, and 24-hour security.
Registration Number: 13970432, TA-178-926-5920-01, GE-178-926-5920-01

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Honolulu

from $203 

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Marina Front Vacation Home in Hawaii Kai with Pool

Experience the perfect getaway at this stunning marina-front property located in peaceful Hawaii Kai. This spacious home offers 3 bedrooms and 2 bathrooms within approximately 1500 sq ft of comfortable living space.
Nestled in a quiet cal-de-sac, the house provides a tranquil retreat with easy access to marina amenities and a large saltwater pool for ultimate relaxation.

Registration Number: GE-005-550-3360-01, 390300300000, TA-005-550-3360-01

• 3 bedroom
• 2 bathroom
• Sleeps 8

Hawaii> Honolulu

from $1,084 

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Hawaiian Hideaway with Ocean Views and Private Beach

This Hawaiian hideaway offers breathtaking unobstructed views of Maunalua Bay with Diamond Head in the distance. Nestled along the coastline in the upscale Portlock community, this four-bedroom, four-bathroom home provides the perfect blend of privacy and luxury.
Registration Number: TA-211-892-4800-01, GE-211-892-4800-01, 390270040000

• 4 bedroom
• 4 bathroom
• Sleeps 8

Hawaii> Honolulu

from $912 

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