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.
Massive 20% Discount for May & June at Aloha Nalu: Lux Home w/ Pool, AC & Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Discover one of Oahu's luxury vacation rentals...
Large upgraded home with space for large extended families
***Luxurious 4-Bedroom Retreat with Ocean Views in Hawaii Kai***Welcome to your dream getaway in the heart of Hawaii Kai! This stunning, newly renovated 4-bedroom, 3-bathroom home offers the perfect blend of luxury, comfort, and breathtaking natural beauty. The house...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Situated in the famed oceanside neighborhood...
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...
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...
Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Enjoy your own waterfront slice of Hawaii at...
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...
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...
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...
New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Located in the upscale neighborhood of...
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...
Hale Kai Lily - Waterfront Hawaiian Getaway
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...
Mahina Kai: Large Tropical Modern Home w/Pool, Ocean / Koko Head Views, & A/C
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Exciting Updates Coming Soon: This property...
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...
Large private home with pool & ocean views - Inquire about dates!
Contact HVROAHU com for more detailsSpectacular 4 bed 2 bath home with private pool and breathtaking ocean and mountain views. Situated on the ridge in the highly desired area of Hawaii Kai. The main level includes a large open kitchen and dining area with plenty of...
Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay
Hale Maunalua - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Breathtaking ocean views greet you at Hale Maunalua, a one-of-a-kind 4BR/4BA hillside hideaway that...
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
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Holoholo Hale by Gather, your...
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...
Stunning Marina Townhome with Ocean and Mountain Views
Premier Marina Front Townhouse with Ocean Views. This large 3 Bedroom 2.5 Bathroom home with Travertine wrap-around patio comes fully equipped for beach & marina fun right off the private dock w/ kayaks, paddleboards, beach chairs & more! The massive master bedroom...
Nanea Kai Villa - Luxury Beachfront Estate in Hawaii Kai
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Nanea Kai Villa by Gather, an...
Enjoyable 5-bedroom house with AC in Honolulu
Quiet neighborhood & desirable 2 story house build in 2023. This tremendous property boasts 5 bedrooms - 3 queen beds and 3 twin beds, perfect for families or groups of friends. With 5 bathrooms and a cozy living room with a sofa bed, guests will have plenty of space to...
Moana Vista by AvantStay | Private Beach + Views
Welcome to Moana Vista, your exclusive waterfront haven nestled between Hauula and Punaluu on Oahu's mesmerizing shores.This beachfront paradise features outdoor amenities abound – a beachfront gym, covered 10-chair gazebo w/ electricity and lighting, lots of hammocks...
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 Ola by Gather: 5BR Secluded Haven w/ Saltwater Pool & Sunset Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Escape to Hale Ola with 20% Off already...
Charming Hawaii Kai home with private pool
***Location and Getting Around***Centrally located in Hawaii Kai! Short walk to Maunalua Bay Beach Park and less than a mile to Safeway, Costco and a handful of restaurants! Less than a ten minute drive in either direction to a number of activities and attractions. Just...
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...
Long term rental Marina Front rental in Hawaii Kai with pool
Beautiful house marina front in Hawaii Kai with pool is available for long term rentalThree bedrooms, two baths, fully furnished with internet and utilities included.30 day minimum rental, no exceptions$18,800/month
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...
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...
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...
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Hale Makana is a luxurious, single-level...
Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees. n
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,...
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,...
Hanapepe House: Newly Renovated Home w/ Private Pool, A/C & Amazing Ocean Views!
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.A Hawaiian hideaway with unobstructed views...