Hawaii Kai Vacation Rentals

Hawaii Kai is one of the largest communities on Oahu's south shore. One advantage of booking a Hawaii Kai vacation rental is that you will be close to Honolulu and Waikiki, where most of the fun and entertainment is happening on Oahu, but away from the hustle and bustle. If you plan to go snorkeling or do other ocean activities, Hawaii Kai is a great place to be since it is close to Hanauma Bay, Oahu's most popular snorkeling destination. Hawaii Kai is located at Maunalua Bay, a popular place for jet skiing, parasailing, kayaking, canoe paddling, diving, fishing and boating.

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

Prices start at $6,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Enjoy your own waterfront slice of Hawaii at Ohana Kai! Located in a gated community along Hawaii Kai’s stunning ...
Registration Number: 390080100000, GE-177-601-5360-01, TA-177-601-5360-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $453 
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Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset

Prices start at $22,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Situated in the famed oceanside neighborhood of Portlock on a rare double-sized ocean lot, this Hawaii Kai vacation...
Registration Number: GE-060-531-3536-01, TA-060-531-3536-01, 390160020000

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $1,242 
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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 ...
Registration Number: TA-025-225-0112-01, GE-025-225-0112-01, 391010920000

  • 6 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,036 
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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. Simply enter your desired dates and click 'Book Now!'


Prepare to be wowed by unforgettable views at this ...
Registration Number: 390310020045, GE-145-848-8320-01, TA-145-848-8320-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $408 
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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 ...
Registration Number: 390020180000, TA-008-452-3520-01, GE-008-452-3520-01

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $593 
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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 ...
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 Kai Home w/Access to the Marina Near Shops & Restaurants

This property is a 30-day minimum rental and is professionally managed by Ali'i Beach Rentals.

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

***This house is new to our inventory. Reviews are coming soon. ...
Registration Number: TA-042-034-1248-01, GE-042-034-1248-01, 390320580000

  • 4 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> honolulu
from $361 
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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 ...
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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New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai

Prices start at $13,500/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Located in the upscale neighborhood of Hawai’i Kai, Nani Wai is a 5-bedroom, 4-bathroom gated home located on a ...
Registration Number: TA-068-282-1120-01, GE-068-282-1120-01, 390950040000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 13
Hawaii> Honolulu
from $795 
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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...
Registration Number: TA-137-893-8880-01, GE-137-893-8880-01, 390230800000, 90/TVU-0258

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,308 
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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 ...
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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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 ...
Registration Number: TA-068-140-0320-01, GE-068-140-0320-01, 390680200000

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $604 
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Mahina Kai: Large Tropical Modern Home w/Pool, Ocean / Koko Head Views, & A/C

Exciting Updates Coming Soon: This property will undergo a redecoration, and new photos will be added shortly!

Welcome to Mahina Kai by Gather, a stunning tropical retreat nestled in a quiet cul-de-sac in Hawaii Kai. With expansive views ...
Registration Number: TA-178-279-8336-01, GE-178-279-8336-01, 390730320000

  • 5 bedroom
  • 4 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $730 
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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 ...
Registration Number: GE-011-442-5856-01, TA-011-442-5856-01, 390750390000

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $436 
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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, ...
Registration Number: 39008004, TA-038-271-2320-01, GE-038-271-2320-01

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $345 
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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. Simply enter your desired dates and click 'Book Now!'

Breathtaking ocean views greet you at Hale Maunalua, a ...
Registration Number: GE-086-598-4512-01, TA-086-598-4512-01, 1390230750000

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $897 
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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. 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...
Registration Number: 1390290370000, GE-085-648-1792-02, TA-085-648-1792-02

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $519 
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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. Simply enter your desired dates and click 'Book Now!'

You’re sure to find your zen at this slice of ...
Registration Number: 390850230000, GE-201-662-2592-02, TA-201-662-2592-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $188 
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Holoholo Hale by Gather w/ Marina Views, Jacuzzi, AC, & Nearby Beaches

Prices start at $8,800/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.

Welcome to Holoholo Hale by Gather, your private waterfront retreat in the serene community of Hawaii Kai on Oahu's ...
Registration Number: TA-024-880-1792-01

  • 4 bedroom
  • 2 bathroom
  • Sleeps 9
Hawaii> Honolulu
from $578 
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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 ...
Registration Number: TA-027-052-6464-01, GE-027-052-6464-01, 39035016

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $383 
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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 ...
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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Hanapepe House: Newly Renovated Home w/ Private Pool, A/C & Amazing Ocean Views!

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...
Registration Number: TA-211-892-4800-01, GE-211-892-4800-01, 390270040000

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $987 
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Hale Makana: Luxury, Pool, AC & Stunning Ocean Views

Hale Makana is a luxurious, single-level estate in Hawaii Kai’s most coveted oceanfront neighborhood. This five-bedroom, seven-bathroom property is the perfect getaway for single and joint families. With front yard views worthy of a postcard, ...
Registration Number: GE-019-591-8336-01, TA-019-591-8336-01, 390270140000

  • 5 bedroom
  • 7 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $1,273 
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Ultimate Oceanfront Luxury Living with Pool and Hot Tub

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

  • 6 bedroom
  • 7 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $10,145 
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Hale Ola by Gather: 5BR Secluded Haven w/ Saltwater Pool & Sunset Views

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. As you step ...
Registration Number: GE-033-454-6944-01, TA-033-454-6944-01, 390270180000

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $1,076 
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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! ...
Registration Number: GE-005-550-3360-01, 390300300000, TA-005-550-3360-01

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $469 
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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/ ...
Registration Number: TA-002-506-5984-01, GE-002-506-5984-01

  • 4 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Hauula
from $1,467 
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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 ...
Registration Number: 390160090000, GE-072-291-2768-01, TA-072-291-2768-01

  • 5 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Honolulu
from $576 
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201 Portlock Rd by Gather: 4BR Beachfront Villa w/ Pool, Oceanviews & Hot Tub

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. This stunning estate, set on a spacious private lot with a beautifully manicured ...
Registration Number: TA-026-671-3600-02, GE-026-671-3600-02, 680270240000

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Honolulu
from $2,348 
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Luxury Hawaii Kai Villa – Ocean Views, Salt Pool & Guest Cottage, 5 Min to Beach

Villa Luana is a dream retreat tucked against a lush Hawaiian mountainside with stunning surroundings that blend natural beauty and upscale luxury. This elegant home invites you to escape into a world of comfort, offering sweeping mountain views...
Registration Number: GE-097-116-5696-02, TA-097-116-5696-02, 39081092

  • 5 bedroom
  • 6 bathroom
  • Sleeps 12
Hawaii> Honolulu
from $507 
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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 ...
Registration Number: TA-089-474-5088-01, GE-089-474-5088-01, 390290290000

  • 4 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Honolulu
from $310 
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Life on the Water Hawaii with WiFi & AC & Washer/Dryer

This delightful cottage in Honolulu is the perfect escape for guests. With a cozy studio unit featuring a queen bed and a sofa bed, this property offers a brilliant space for relaxation. Enjoy the convenience of amenities like WiFi, AC, and a ...
Registration Number: TA-099-507-2000-01, GE-099-507-2000-01, 390500130000

  • 1 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Honolulu
from $147 
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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. This property was the ...
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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