Luxury Vacation Rentals in Hawaii Kai, Oahu
Hawaii Kai vacation rentals offer upscale accommodations on Oahu's scenic southeast coast. Choose from marina-front homes, luxury townhouses, and oceanview condos near Hanauma Bay, Koko Crater, and Maunalua Bay – ideal for travelers who want comfort, privacy, and proximity to both nature and city life.
Upscale Coastal Living Near Honolulu
Hawaii Kai is one of Oahu's most desirable residential communities, known for its spacious marina neighborhoods, oceanfront homes, and easy access to both natural wonders and urban attractions. Located just 20 minutes from Waikiki, Hawaii Kai offers a quieter, more scenic experience with high-end accommodations perfect for families, couples, and digital nomads.
Top Attractions Near Hawaii Kai
- Hanauma Bay Nature Preserve – premier snorkeling in protected reef waters
- Koko Head Crater Trail – a challenging climb with panoramic views
- Maunalua Bay – ideal for kayaking, SUP, and boating
- Hawaii Kai Towne Center – shopping, groceries, restaurants, and marina views
Key Features of Hawaii Kai Vacation Rentals
- Spacious homes and condos with marina or ocean views
- Private lanais, full kitchens, air conditioning, and free Wi-Fi
- Pool access, tropical landscaping, and outdoor entertainment areas
- Proximity to grocery stores, Costco, and waterfront dining
- Family-friendly layouts and executive work-from-paradise options
Who Should Stay in Hawaii Kai?
- Couples or families seeking luxury without the bustle of Waikiki
- Nature lovers who want to be near scenic hiking and snorkeling spots
- Professionals and long-term travelers needing space and amenities
- Boating and paddling enthusiasts who want access to Maunalua Bay
Explore More Nearby
If you're looking for additional upscale stays nearby, explore rentals in Kahala, Waikiki, or along Oahu's Windward Coast. Each offers its own unique mix of scenery and access.
Browse our curated selection of Hawaii Kai vacation rentals below and discover a sophisticated stay in one of Oahu's most scenic and peaceful communities.
Large Luxury Home w/ pool and Ocean Views. Special discounted rate March 2025
This magnificent architectural masterpiece - a luxury home that captures an unobstructed 180-degree vistas of the Pacific Ocean, stretching from the iconic Diamond Head to Koko Kai awaits you. Enjoy ever-changing views, from sunrise to sunset, a daily spectacle. Nestled...
Designer Condo in Hawaii Kai! Close to beaches, shopping, hiking!
Kick back and relax in this calm, stylish condo located in Hawaii Kai in east Honolulu. This newly redesigned condo is outfitted with brand new, high end furniture to match the allure of the beautiful, newly constructed building and fabulous amenities.This beautiful...
Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional...
Island Style Elegance on a Beach Access
Island style elegance with beach access.Immerse yourself in the island inspired luxury of Portlock Paradise. Sitting on large lush ocean access property, Portlock Paradise offers four bedrooms, 3 with ensuite bathrooms, an indoor and outdoor dining areas, elegant...
Executive Balinese Vacation Home in Hawaii Kai
Find serenity,luxurious style, at Hale Maluhia. This Oahu vacation rental, whose Hawaiian name translates to "house of tranquility," is a beautifully contemporary resort close to some of the island's best beaches and east oahu coastline. Invite up to eight friends or...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
This expansive oceanfront estate, Maunalua Sunset, sits on a rare double-wide lot along the calm shoreline of Maunalua Bay in Portlock. Multiple standalone structures wrap around a lush courtyard and resort-style pool, creating a private sanctuary designed for extended...
NEW Modern Marina Front on Hawaii Quay
Enjoy marina-front living in Hawaii Kai at it's finest! This upgraded single-level four bedrooms, four bathrooms home's large lanai with pergola overlooks your own private dock. Watch the ducks swim by or take the kayak and stand up paddle out to the beach. West-facing...
Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool
Ohana Kai offers the rare chance to stay directly along the tranquil waters of Hawaii Kai’s marina, blending the ease of island living with the comforts of a contemporary home. Set within a private gated community on Oahu’s south shore, this two-story corner condo...
Please contact me for specific dates that you may be interested in.
This is your home away from home in an immaculate, spaciously designed guest house built for relaxing in comfort, style & convenience. This an attached 2 bedroom + 2 bath fully-equipped house + sofa bed and a very large stocked kitchen with a separate entrance and foyer...
Spacious Cottage with A/C and Patio
New build spacious cottage in quiet upscale neighborhood just steps away from famous China Walls. The unit is detached from the main house with its own private entrance. It includes a private grassy patio with a plumeria tree. Covered parking right by the front door....
Ocean View Cottage with Separate Suite
Incredible COTTAGE! with a new Separate Suite! How can you vacation in Hawaii and not have an ocean view!! Authentic Hawaii vacation retreat in Hawaii Kai-East Side of Oahu! Get away from the hustle and bustle of everyday day life, rejuvenate, and revitalize yourself at...
Luxurious Hawaiian Villa Oasis
A mini resort tucked away in an upscale and peaceful neighborhood, this Villa is absolutely one of a kind! The entire Villa has just been exquisitely renovated with a swimming pool, Bali house, and waterfall. The landscaping is so immaculate, our guests rarely want to...
PARADISE PROMISED! Spacious 6 bedroom home. Minimum Stay
This property will only be made available once every 30 days to comply with the Hawaii rental laws. Rental contracts will reflect a 30 day rental period and no other guests may occupy the home during that time period. Please contact us for further information prior to...
Wonderful retreat, Fantastic View, Immaculate, Beautiful, Private and Peaceful!
Enjoy gorgeous unobstructed ocean, marina & mountain views from our beautiful guest house. Located on the ridge, in a safe, quiet and upscale neighborhood in Hawaii Kai, East Honolulu, just around the corner from famous Hanauma Bay, Halona Blow Hole, spectacular Sandy...
Hale Kai Lily - Waterfront Hawaiian Getaway 10% discount for November 2025
This single-level waterfront, home is thoughtfully curated & designed. New AC in every room. Featuring a full kitchen, living room, and lanai as well as 4 bedrooms and 3 bathrooms. The property is fully furnished and boasts captivating marina views from all common areas...
Waterfront home of peaceful joy: Villa Laule'a
Welcome to Villa Laule'a~~Hawaiian for peaceful happiness. This beautifully furnished & well equipped 4 bedroom townhouse is ready for your luxury vacation. Fine sheets and towels, fabulous kitchen. You'll enjoy the waterfront lagoon and close access to the ocean....
Hale Ohana, Private, Oceanview home w/pool, Licensed TAT home
Set on the slopes of Koko Kai, this spacious, two-story, family-style home offers panoramic ocean views and breathtaking sunset over Diamond Head. Decorated with a touch of island decor, this villa is perfect for indoor/outdoor living. The large full kitchen, two living...
New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai
Nani Wai is a five-bedroom, four-bathroom private retreat tucked into the prestigious Hawai‘i Kai neighborhood of Honolulu, O‘ahu. With its enviable waterfront perch on a private marina and unobstructed views of Koko Crater, this gated home delivers a seamless blend of...
Honolulu Waterfront Oasis
True Hawaiiana at its best! Luxury 3 bedroom 2.5 bath waterfront home with pool, spa, tiki bar, boat dock, two 60 inch flat screen TV's /DVD movie surround systems, Bose outdoor music near pool, granite, slate, and many more upgrade too numerous to mention. Located near...
Large private home with pool & ocean views - Inquire about dates!
This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. Spectacular 4 bed 2 bath home with private pool and breathtaking ocean and mountain views. Situated on the ridge in the highly desired area of...
Mahina Kai: Large Tropical Modern Home with Pool, Ocean & Koko Head Views & A/C
Welcome to Mahina Kai, a serene 5-bedroom, 3-bath retreat in Hawaii Kai offering panoramic views of Koko Crater, the marina, and the deep blue Pacific. This beautifully designed two-level home spans approximately 2,567 sq ft of bright indoor–outdoor living, featuring...
7-BEDROOM HOME SPECTACULAR POOL WALK EVERYWHERE AROUND HAWAII KAI!
Hawaii Kai home is in a Prime Location with circular view of surrounding mountains including Koko Head Mountain. Also includes a view of the Koko Marina from the Lanai. Walking distance to Hanauma Bay (less than a mile), Koko Head Mountain (.5 miles), and...
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock
Experience Oahu like a Kama'aina (local) in this 3 bedroom, 2 1/2 bath waterfront home. Safe community. Views from every room. Private lanai, BBQ grill, community pool, and boat dock. Walk to dining, shopping, bars, farmers market, hiking, beaches. 5 minutes drive to...
Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach
Kaiwiki PalaceOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on a quiet cul-de-sac just minutes from the ocean, this 3BR/2BA home is perfect for a serene tropical escape....
Zen home with fast WiFi, washer/dryer, koi pond & large lanai
Seabreeze Hawaii Kai -A - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’re sure to find your zen at this slice of paradise. From a gorgeous lanai to a lush...
Holoholo Hale by Gather w/ Marina Views, Jacuzzi, AC, & Nearby Beaches
Welcome to Holoholo Hale, a private waterfront retreat tucked into the peaceful marina community of Hawaii Kai in South Oahu. This single-level home pairs open, contemporary living spaces with tranquil outdoor areas designed for relaxation and gathering. With four...
Private Oceanfront 5BR! Family Home Hawaii Kai
Ultimate retreat nestled in a chic oceanfront locale. This private oceanfront residence boasts its very own private staircase that descends to the breathtaking shores of Maunaloa Bay. Conveniently situated in the heart of Portlock, you'll find yourself just a stone's...
Waterfront Kuapa Isle gem with Koko Crater views & pool - by the beach
Kuapa Isle Gem Unit 419 - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This dreamy 2BR/2.5BA waterfront rental overlooks Koko Crater and a glittering blue lagoon....
Hawaii Kai Dream with large lanai, ocean views, & a home office - near beaches
Hawaii Kai Dream - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Prepare to be wowed by unforgettable views at this 4BR/3BA home, ideally situated in Honolulu’s...
Home with ocean views, studio, large lanai, koi pond, washer/dryer
Seabreeze Hawaii Kai - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape from the hustle and bustle of everyday life to this slice of paradise! You are sure to...
Luxury Hawaii Kai Villa – Ocean Views, Salt Pool & Guest Cottage, 5 Min to Beach
Villa Luana – Relaxed Comfort in Hawaii KaiVilla Luana is a peaceful retreat set against the green mountains of Hawaii Kai. With views of the surrounding landscape and glimpses of the ocean, it’s a great place to unwind and enjoy the slower pace of island life.Inside,...
Hawaii Kai ~ Central Location ~ Oahu Perfection!
Stylish 3 bedroom, 3 bathroom home in centrally located Hawaii Kai. Walkable to shopping, grocery and fabulous restaurants! Enjoy the A/C or hang out on the beautiful lanai. Located in a sweet neighborhood near Koko Marina, you can easily walk to the beach to fish,...
Waterfront Bliss at Tropical Townhouse
Step into your own slice of paradise with this beautifully updated waterfront 3-bedroom, 2-bath ground-floor townhome in the exclusive, gated enclave of Mawaena Kai. Nestled along the marina’s edge, this breezy retreat offers the perfect blend of coastal charm and...
Serene Sandy Beach Golf Course Home
***Location and Getting Around***Welcome to the heart of Hawaii Kai—your gateway to adventure and relaxation! Just a 5-minute stroll brings you to the golden sands of Sandy Beach, perfect for sunrise walks or catching waves. Hungry or need supplies? You're only a few...
Amazing views! Exclusive & peaceful Hawaii Kai. Walk to ocean & hikes, Pool, AC,
A pristine, quiet neighborhood on the backside of Hanauma Bay, your Honolulu/Oahu adventure begins at this lovely 4-bedroom house. With 2 king beds, 1 full bed, and 1 queen bed, this newly rebuilt property is perfect for families or small groups of friends. Three of the...
Glam Mid Century Modern 4-bedroom oceanfront estate in wonderful Honolulu
30 day minimum rental. YOU are James Bond (or a James Bond villain!) in this oceanfront architectural marvel with its own beach and cove!!! Site of dozens of editorial fashion, film and television shoots. Check out our socials at midcenturyhonolulu. This property was...
2 bed 2 bath Hawaii Kai Getaway
This fully furnished 2 bed, 2 bath unit with 1 parking spot located in Hawaii Kai is a peaceful getaway spot. The unit features a full kitchen, spacious living & dining area, master bedroom, 2nd bedroom, and a 2nd bathroom. The master bathroom features a vanity with...
Nanea Kai Villa - Luxury Beachfront Estate in Hawaii Kai
At Nanea Kai Villa, ocean breezes, Diamond Head views, and beachfront living come together in a spacious four-bedroom retreat. This two-story estate offers 4,700 sq. ft. of refined island living, complete with a heated saltwater pool, spa, and private beachfront access...
RARE find! Stunning Views! 3-BR house with pool, WiFi, AC in quiet Honolulu area
Discover the beauty of Honolulu from this 3-bedroom artists' home. This property features 1 king bed, 1 queen bed, and 1 bunk bed, 3.5 bathrooms including 3 bathtubs and 2 bidets - perfect for families or friends traveling together. Guests can relax and unwind in the...
Charming room near Hanauma Bay
Charming room in the heart of Hawaii Kai. A block away from amazing restaurants, cafes, bars and so much more. Perfect for business trips while exploring everything Oahu has to offer. Near famous beaches and hiking trails - 5 minutes from Hanauma Bay (one of the best...
Designer Studio in Hawaii Kai! Close to beaches, shopping, and hiking!
Come and enjoy this newly updated and professionally designed studio in beautiful Hawaii Kai. This fresh and inviting space is the perfect getaway and launch pad for all of your Hawaii adventures or just to relax and get away from it all.This is a gorgeous, designer...
Tranquil Marina Front Pool House Resort
Marina Front Property in peaceful Cal-De-Sac with large tranquil salt water pool and marina access.Spacious outdoor patio lounge with BBQ grill and prep station and patio furniture and large TV.Parking for two cars! Close to Hanauma Bay, Kona Brewery, Costco, Koko Head,...
Hale Ola: 5BR Portlock Luxury Home with Saltwater Pool
Nestled in Honolulu’s prestigious Portlock neighborhood, Hale Ola is a refined coastal retreat where luxury, comfort, and panoramic ocean views come together seamlessly. This single-level estate spans 3,744 square feet and accommodates up to twelve guests across five...
Sea Cliff Chic – Ultra-Luxury Oceanfront Retreat in Portlock
Sea Cliff Chic is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego-based developer Mark Gosselin. This Oahu vacation home is a modern take on Oahu’s well-known Honeyed Jade. This...
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
Set along Oahu’s exclusive Portlock coastline, Hale Makana is a refined single-level oceanfront estate that celebrates effortless island living. With postcard-worthy views of Diamond Head and the deep blue Pacific, this five-bedroom, seven-bath retreat blends...
Hanapepe House: Newly Renovated Home w/ Private Pool, A/C & Amazing Ocean Views!
Set along O‘ahu’s dramatic Portlock coastline, Hanapepe House by Gather is a rare 4-bedroom, 4.5-bath oceanfront retreat offering unobstructed views of Maunalua Bay, Koko Head, and Diamond Head. With 4,274 sq. ft. of interior living space, a private pool, wraparound...
Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees.
Amazing ocean, marina and mountain views.. Enjoy the relaxing and peaceful resort lifestyle, in this one of a kind recently remodeled unit. Designer decorated, new flooring, upgraded appliances, kitchen and bathroom. Resort like amenities include fitness center,...