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 and luxury condos near Hanauma Bay, Koko Crater, and Maunalua Bay - perfect for travelers seeking comfort, space, and a quieter alternative to Waikiki.

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.

⌄

Sort By

List

Map

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

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

from $428

View Property Book Direct

Large upgraded home with space for large extended families

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.
Registration Number: 390801160000, GE-165-444-6592-01, TA-165-444-6592-01

4 bedroom
3 bathroom
Sleeps 8

from $377

View Property Book Direct

$Lavish Oceanfront Estate w\/Pool, Spa & AC - Close to Beaches: Maunalua Sunset$

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 of Portlock on a rare double-sized ocean lot, this Hawaii Kai vacation rental home provides the ultimate in privacy and accommodations for your large group.
Registration Number: GE-060-531-3536-01, TA-060-531-3536-01, 390160020000

6 bedroom
6 bathroom
Sleeps 12

from $1,407

View Property Book Direct

Executive Balinese Vacation Home in Hawaii Kai

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 family members to enjoy this four-bedroom luxury property nestled beneath spectacular Kamehame Ridge and across Koko crater.
Registration Number: TA-025-225-0112-01, GE-025-225-0112-01, 391010920000

5 bedroom
3 bathroom
Sleeps 10

from $1,036

View Property Book Direct

Designer Condo in Hawaii Kai! Close to beaches, shopping, hiking!

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.

Registration Number: 1390080680063, TA-181-932-1856-01, GE-181-932-1856-01

2 bedroom
1 bathroom
Sleeps 4

from $162

View Property Book Direct

$Ohana Kai: Modern Water Front Condo w\/Gorgeous Views, A\/C, Yard, & Shared Pool$

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

3 bedroom
2 bathroom
Sleeps 8

from $397

View Property Book Direct

$Waterfront Hawaii Kai Home w\/Access to the Marina Near Shops & Restaurants$

Waterfront Hawaii Kai Home w/Access to the Marina Near Shops & Restaurants

This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.

Please Note: No weddings, memorials, large parties or pets allowed.

Nestled in an idyllic Hawaii Kai location, this exquisite island home provides a comprehensive array of amenities.
Registration Number: TA-042-034-1248-01, GE-042-034-1248-01, 390320580000

4 bedroom
2 bathroom
Sleeps 8

from $264

View Property Book Direct

Please contact me for specific dates that you may be interested in.

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 for complete privacy.
Registration Number: GE-114-345-1648-01, TA-114-345-1648-01, 126021026000

2 bedroom
2 bathroom
Sleeps 6

from $511

View Property Book Direct

Ocean View Cottage with Separate Suite

Incredible COTTAGE! with a new Separate Suite! 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 this unique property. This vacation cottage is nestled in the lush mountain forest on the east side of Oahu (Hawaii Kai).
Registration Number: 390830520000, GE-060-165-9392-01, TA-060-165-9392-01

1 bedroom
1 bathroom
Sleeps 6

from $361

View Property Book Direct

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 poolside seating next to a large tropical pool and a expansive lush lawn and garden.
Registration Number: 390020180000, TA-008-452-3520-01, GE-008-452-3520-01

4 bedroom
4 bathroom
Sleeps 10

from $707

View Property Book Direct

$New Listing! Marina-front Home Near the Ocean w\/Private Pool & AC: Nani Wai$

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 Hawai’i Kai, Nani Wai is a 5-bedroom, 4-bathroom gated home located on a marina and with views of the majestic Koko Crater.
Registration Number: TA-068-282-1120-01, GE-068-282-1120-01, 390950040000

5 bedroom
4 bathroom
Sleeps 13

from $837

View Property Book Direct

Waterfront home of peaceful joy: Villa Laule'a

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.
Registration Number: TA-124-812-6976-01, GE-124-812-6976-01

4 bedroom
3 bathroom
Sleeps 6

from $321

View Property Book Direct

$Hale Ohana, Private, Oceanview home w\/pool, Licensed TAT home$

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 room areas, and large lanais provide plenty of room for families and friends to relax.

Registration Number: TA-137-893-8880-01, GE-137-893-8880-01, 390230800000, 90/TVU-0258

3 bedroom
3 bathroom
Sleeps 10

from $1,306

View Property Book Direct

Hale Kai Lily - Waterfront Hawaiian Getaway

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 and the master bedroom.
Registration Number: TA-068-140-0320-01, GE-068-140-0320-01, 390680200000

4 bedroom
3 bathroom
Sleeps 8

from $666

View Property Book Direct

$Mahina Kai: Large Tropical Modern Home w\/Pool, Ocean \/ Koko Head Views, & A\/C$

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 will undergo a redecoration, and new photos will be added shortly!

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

5 bedroom
3 bathroom
Sleeps 12

from $1,253

View Property Book Direct

$Waterfront Home near Beach. Peaceful Community w\/ Swimming Pool and Boat Dock$

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.
Registration Number: 39008004, TA-038-271-2320-01, GE-038-271-2320-01

3 bedroom
2 bathroom
Sleeps 6

from $337

View Property Book Direct

Large private home with pool & ocean views - Inquire about dates!

Large private home with pool & ocean views - Inquire about dates!

Contact HVROAHU com for more details

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 Hawaii Kai.

The main level includes a large open kitchen and dining area with plenty of space for a large family to congregate in.
Registration Number: GE-011-442-5856-01, TA-011-442-5856-01, 390750390000

4 bedroom
2 bathroom
Sleeps 8

from $577

View Property Book Direct

Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay

Hale Maunalua hillside hideaway with ocean views & pool - walk to Hanauma Bay

Hale Maunalua - 30-Night Minimum

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

Breathtaking ocean views greet you at Hale Maunalua, a one-of-a-kind 4BR/4BA hillside hideaway that features three levels of luxurious indoor/outdoor entertaining space.
Registration Number: GE-086-598-4512-01, TA-086-598-4512-01, 1390230750000

4 bedroom
4 bathroom
Sleeps 10

from $829

View Property Book Direct

Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach

Tropical Escape with Lanai & Private Yard | Walk to Maunalua Bay Beach

Kaiwiki Palace

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

Located on a quiet cul-de-sac just minutes from the ocean, this 3BR/2BA home is perfect for a serene tropical escape. Relax on the lanai or in the private yard and enjoy meals al fresco under the tall palms.

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

3 bedroom
2 bathroom
Sleeps 6

from $581

View Property Book Direct

$Zen home with fast WiFi, washer\/dryer, koi pond & large lanai$

Zen home with fast WiFi, washer/dryer, koi pond & large lanai

Seabreeze Hawaii Kai -A - 30-Night Minimum

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

You’re sure to find your zen at this slice of paradise. From a gorgeous lanai to a lush garden, this stunning home offers exceptional outdoor space.
Registration Number: 390850230000, GE-201-662-2592-02, TA-201-662-2592-01

3 bedroom
2 bathroom
Sleeps 6

from $332

View Property Book Direct

$Holoholo Hale by Gather w\/ Marina Views, Jacuzzi, AC, & Nearby Beaches$

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 private waterfront retreat in the serene community of Hawaii Kai on Oahu's stunning marina.
Registration Number: 390290010000, GE-024-880-1792-01, TA-024-880-1792-01

4 bedroom
2 bathroom
Sleeps 9

from $546

View Property Book Direct

Hawaii Kai Dream with large lanai, ocean views, & a home office - near beaches

Hawaii Kai Dream with large lanai, ocean views, & a home office - near beaches

Hawaii Kai Dream - 30-Night Minimum

Our calendar is updated in real-time & our nightly rates are accurately displayed. '

Prepare to be wowed by unforgettable views at this 4BR/3BA home, ideally situated in Honolulu’s beautiful Hawaii Kai.

Registration Number: 390310020045, GE-145-848-8320-01, TA-145-848-8320-01

4 bedroom
3 bathroom
Sleeps 8

from $419

View Property Book Direct

Stunning Marina Townhome with Ocean and Mountain Views

Stunning Marina Townhome with Ocean and Mountain Views

Premier Marina Front Townhouse with Ocean Views. 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 looks over the marina to the ocean & beautiful Koko Head.
Registration Number: TA-027-052-6464-01, GE-027-052-6464-01, 39035016

4 bedroom
2 bathroom
Sleeps 8

from $383

View Property Book Direct

$201 Portlock Rd by Gather: 4BR Beachfront Villa w\/ Pool, Oceanviews & Hot Tub$

201 Portlock Rd by Gather: 4BR Beachfront Villa w/ Pool, Oceanviews & Hot Tub

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 exquisite four-bedroom, three-and-a-half-bathroom beachfront villa nestled along the serene shores of Hawaii Kai, Hawaii.
Registration Number: TA-026-671-3600-02, GE-026-671-3600-02, 680270240000

4 bedroom
3 bathroom
Sleeps 8

from $2,711

View Property Book Direct

Moana Vista by AvantStay | Private Beach + Views

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 and patio chairs, an outdoor BBQ grill, and 3 newly-added beachfront hot tubs, with the third being a sizeable 7-person spa.
Registration Number: TA-002-506-5984-01, GE-002-506-5984-01

4 bedroom
3 bathroom
Sleeps 10

from $1,313

View Property Book Direct

Sea Cliff Chic – Ultra-Luxury Oceanfront Retreat in Portlock

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

6 bedroom
6 bathroom
Sleeps 12

from $11,568

View Property Book Direct

$Hale Ola by Gather: 5BR Secluded Haven w\/ Saltwater Pool & Sunset Views$

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 40% Off May & June – A Rare Opportunity to Experience Island Luxury for Less

Come and experience the beauty of Hale Ola by Gather, an exquisite secluded haven situated in the prestigious Portlock neighborhood, offering awe-inspiring ocean views, Diamond Head, and majestic mountains from every perspective.
Registration Number: GE-033-454-6944-01, TA-033-454-6944-01, 390270180000

5 bedroom
5 bathroom
Sleeps 12

from $1,143

View Property Book Direct

Charming Hawaii Kai home with private pool

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.
Registration Number: TA-089-474-5088-01, GE-089-474-5088-01, 390290290000

3 bedroom
2 bathroom
Sleeps 6

from $275

View Property Book Direct

Glam Mid Century Modern 4-bedroom oceanfront estate in wonderful Honolulu

Glam Mid Century Modern 4-bedroom oceanfront estate in wonderful Honolulu

30 day minimum rental. Site of dozens of editorial fashion, film and television shoots. Check out our socials at midcenturyhonolulu. This property was the vacation rental for Frank Sinatra, Elvis Presley, Tom Jones, Sting, and most importantly Paul McCartney who wrote Silly Love Songs right here at the piano in the corner of the living room during his months long stay here in the mid-seventies.
Registration Number: TA-111-279-1552-01, GE-111-279-1552-01, 390280170000

4 bedroom
5 bathroom
Sleeps 10

from $1,488

View Property Book Direct

Luxury Hawaii Kai Villa – Ocean Views, Salt Pool & Guest Cottage, 5 Min to Beach

Luxury Hawaii Kai Villa – Ocean Views, Salt Pool & Guest Cottage, 5 Min to Beach

Villa Luana – Relaxed Comfort in Hawaii Kai

Villa 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.

Registration Number: GE-097-116-5696-02, TA-097-116-5696-02, 39081092

4 bedroom
3 bathroom
Sleeps 12

from $465

View Property Book Direct

Private Oceanfront 5BR! Family Home Hawaii Kai

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 throw away from marina-front dining, boutique shops, a water sports activity center, a fitness facility and grocery stores.
Registration Number: 390160090000, GE-072-291-2768-01, TA-072-291-2768-01

5 bedroom
3 bathroom
Sleeps 10

from $696

View Property Book Direct

Hale Makana: Luxury, Pool, AC & Stunning Ocean Views

Hale Makana: Luxury, Pool, AC & Stunning 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 estate in Hawaii Kai’s most coveted oceanfront neighborhood.
Registration Number: GE-019-591-8336-01, TA-019-591-8336-01, 390270140000

5 bedroom
7 bathroom
Sleeps 10

from $1,596

View Property Book Direct

$Breathtaking Ocean Views! Peaceful Retreat\/No Resort Fees. \n$

Breathtaking Ocean Views! Peaceful Retreat/No Resort Fees. n

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, racquetball, swimming pools, hot tubs, BBQ areas, manicured landscaping, recreation facilities and 24 hour security, one cover parking space (additional parking available on street or for rent) Minutes walk to Oahu club, Safeway, restaurants, and 15 minutes to downtown Honolulu.
Registration Number: 13970432, TA-178-926-5920-01, GE-178-926-5920-01

1 bedroom
1 bathroom
Sleeps 4

from $203

View Property Book Direct

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, and much more.

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

3 bedroom
2 bathroom
Sleeps 8

from $1,084

View Property Book Direct

$Hanapepe House: Newly Renovated Home w\/ Private Pool, A\/C & Amazing Ocean Views!$

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 overlooking Maunalua Bay and with the iconic Diamond Head in the distance, Hanapepe house is not only nestled along the coastline, but also has private shoreline access, so you can walk right up to the water line.
Registration Number: TA-211-892-4800-01, GE-211-892-4800-01, 390270040000

4 bedroom
4 bathroom
Sleeps 8

from $912

View Property Book Direct

Showing 1 of 1 pages.