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.

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  • Private Boutique Resort in Hawaiian Paradise-Lush Backyard, Pool, Wifi & BBQ!


    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 ...
    Registration Number: 570010130038, TA-088-128-9216-01, GE-088-128-9216-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 16
    Hawaii> Honolulu
    3  reviews
    from $447 
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  • Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool. Ohana Kai

    Enjoy your own waterfront slice of Hawaii at Ohana Kai! Located in a gated community along Hawaii Kai’s stunning waterway, you’ll enjoy marina and Koko Head views from every room. Unwind in the casual charm of this peaceful paradise with its...
    Registration Number: TA-177-601-5360-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    1  reviews
    from $229 
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  • Honolulu Luxury Home w/Cottage, Private Saltwater Pool & Observatory Deck

    Villa Luana (meaning happy or content) provides an ideal setting for relaxing in blissful comfort. With several living spaces, a gourmet kitchen, and a large dining area, HIGH SPEED WIFI, this elegant home perfectly accommodates everything from ...
    Registration Number: TA-192-269-3632-01, 390810920000, GE-192-269-3632-01

    • 6 bedroom
    • 7 bathroom
    • Sleeps 14
    Hawaii> Honolulu
    12  reviews
    from $1,025 
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  • Now through Oct 2023 Discounted to 15-18k per month! Spend the summer in Hawaii

    This property is a legally established dwelling that is rented for periods of 30 days or more at any one time. Contact us for more details.

    This remarkable property is located in the highly sought-after East Honolulu neighborhood and is ...
    Registration Number: GE-011-442-5856-01, TA-011-442-5856-01, 390130180000

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    11  reviews
    from $685 
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  • Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset

    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. Multiple estate structures surround a ...
    Registration Number: 390160020000, TA-060-531-3536-01, GE-060-531-3536-01

    • 6 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    1  reviews
    from $683 
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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: 391010920000, GE-025-225-0112-01, TA-025-225-0112-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    2  reviews
    from $599 
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  • Private, Peaceful & Prestigious Home w/ Ocean, other Islands, and Mountain Views

    Open floor plan, over 1500 sq. ft., filled w/ imported Chinese furniture, beautiful ocean, other islands, mountain views, full size decks - master bedroom & dining room, full size kitchen w/ appliances, house sits back from the road - private, ...
    Registration Number: TA-174-234-4192-01, 1390760570000, GE-174-234-4192-01

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    3  reviews
    from $160 
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  • Marina Front House with Private Water Access, Peaceful and Serene

    Waterfront access in this beautiful Hawaii Kai home. Relax with the whole family at this peaceful place to stay. Enjoy paddling from your private dock. Close to beaches, restaurants, shopping and activities.

    Please inquire for flexible ...
    Registration Number: 390300450000, TA-100-967-8848-01, GE-100-967-8848-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 7
    Hawaii> Honolulu
    4  reviews
    from $310 
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  • Beachfront Luxury Villa

    The mayor and city council have conspired to put short term rentals out of business and hand the hotels a 100% monopoly on vacation accommodations. They are requiring us to advertise and quote a 30 night rental rate. You can stay as few or as ...
    Registration Number: GE-048-406-5280-01, TA-048-406-5280-01, 1390020080000

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    2  reviews
    from $1,500 
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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: TA-008-452-3520-01, 390020180000, GE-008-452-3520-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    1  reviews
    from $571 
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  • Cheerful, 3 bedroom, Waterfront Townhome with Spa! NO CLEANING FEE!

    Pa`ani Hale (Play House) it is a 3 bedroom 2.5 bath, two-story waterfront townhouse!
    Enjoy all the toys provided, including an in deck spa, pool table with table tennis topper, one double kayak, two SUPs, a Pac-Man machine, a bar area and ...
    Registration Number: 390080040033,GE-036-485-6832-01,TA-036-485-6832-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    1  reviews
    from $471 
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  • PARADISE PROMISED! Spacious 6 bedroom private home with salt pool, full AC


    This home has been registered as a Transient Accommodation with the State of Hawaii TA-130-584-7808-01. GE-130-584-7808-02.
    No weddings or special events are permitted on site. Strictly enforced 9:00 pm quiet time ( no pool ...
    Registration Number: 390240060000, GE-130-584-7808-02, TA-130-584-7808-01

    • 6 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    85  reviews
    from $1,250 
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  • EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW.

    "Wow!" is the usual reaction of folks seeing the view from this traditional Hawaiian home. Furnished comfortably, with attention to detail for a wonderful, relaxing vacation. Spectacular sunsets. In winter, humpback whales cavort in the ocean ...
    Registration Number: 390280160000, TA-166-425-8048-01, GE-166-425-8048-02

    • 4 bedroom
    • 3 bathroom
    • Sleeps 9
    Hawaii> Honolulu
    51  reviews
    from $384 
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  • 15% off for monthly reservations! Fantastic View, Immaculate, Beautiful,Peaceful

    Enjoy gorgeous unobstructed ocean, marina & mountain views from our beautiful newly built 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, ...
    Registration Number: 390750020000, GE-040-238-6944-01, TA-040-238-6944-01

    • 2 bedroom
    • 1 bathroom
    • Sleeps 5
    Hawaii> Honolulu
    175  reviews
    from $192 
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  • Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking

    ****Contact Owners for stays other than 30 days***
    Step away from noise and traffic of Waikiki and join us in heavenly Hahaione valley. This quiet home is just minutes from Moanalua bay, a must for the water the water sports enthusiast and ...
    Registration Number: TA-088-558-4896-01,GE-088-558-4896-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    29  reviews
    from $134 
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  • Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head Views,Aloha Nalu

    Discover one of Oahu's luxury vacation rentals with its gorgeous private pool terrace overlooking the Pacific Ocean and Diamond Head, Aloha Nalu (meaning “warm, welcoming sea”) will surely sweep you into the spirit of aloha. The villa sits ...
    Registration Number: TA-019-941-5808-01, GE-019-941-5808-01, 390130060000

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    12  reviews
    from $980 
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  • 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: GE-060-165-9392-01, 390830520000, TA-060-165-9392-01

    • 0 bedroom
    • 1 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    53  reviews
    from $405 
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  • Secluded waterfront home-lava waterfall, saltwater pool, spa, sauna

    MARINA SPA HOUSE
    A waterfront playground located just 15 minutes from Waikiki, this private house in the upscale neighborhood of Hawaii Kai has more amenities: air conditioning, boasts a large floating deck for recreation, a heated saltwater ...
    Registration Number: GE-098-023-4672-01, 390930980000, TA-098-023-4672-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    56  reviews
    from $841 
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  • Koko Head Casa - Hip Modern Home Close to Hanauma Bay and Koko Crater

    In accordance with City and County of Honolulu ordinances, this property may not be rented for less than 30 consecutive days.

    Renters will have exclusive use of the property for the full 30 days but may choose to occupy the property for ...
    Registration Number: 390541480000, TA-111-596-4416-01, GE-111-596-4416-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    17  reviews
    from $495 
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  • New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai

    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. This spacious home is ideal for larger groups, with lots of room to spread out ...
    Registration Number: 390950040000, TA-068-282-1120-01, GE-068-282-1120-01

    • 5 bedroom
    • 4 bathroom
    • Sleeps 13
    Hawaii> Honolulu
    7  reviews
    from $701 
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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
    7  reviews
    from $230 
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  • Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views

    This property is a legal dwelling rented for 30 or more consecutive days.
    Contact owner for more details and pricing 🌴 Darrenperman@me.com


    A Rare Private House in Hawaii! This family-friendly house is 'On the Water' with boat ...
    Registration Number: TA-071-856-5376-01, 390320140000, GE-071-856-5376-01

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    66  reviews
    from $599 
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  • Hale Ohana, Private, Oceanview home w/pool

    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

    • 3 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    30  reviews
    from $755 
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  • Marina front home with Koko Crater views & sparkling blue Makapu'u Pool!

    Oahu requires a 30 day rental, call for details.

    Please email or call regarding longer stays

    Kuapa Villa is a quaint 2,000 square foot interior, recently remodeled, marina-front, simple relaxing older home with A/C in all bedrooms ...
    Registration Number: 139052027000, GE-030-168-0640-01, TA-030-168-0640-01

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    57  reviews
    from $575 
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  • Large Tropical Modern Home w/Pool, Ocean / Koko Head Views, & A/C. Makani Lani

    Make lasting memories with your family in this tropical retreat. Located in Hawaii Kai on a quiet cul-de-sac, Makani Lani provides expansive views and a spa-like setting near all the attractions of south Oahu.

    The main floor of Makani ...
    Registration Number: GE-178-279-8336-01, TA-178-279-8336-01, 390730320000

    • 5 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    5  reviews
    from $651 
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  • Newly Renovated Marina-Water Front Luxury Home

    Aloha! This newly renovated 5 bedrooms, 3-bathroom home is located on the desirable east side of Oahu (Hawaii Kai.) This beautiful marina-front property with private water access boasts incredible 360-degree views of surrounding mountains and ...
    Registration Number: GE-093-063-5776-01, 390500150000, TA-093-063-5776-01

    • 5 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    31  reviews
    from $850 
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  • Large private home with pool - September & October - Fall special - 10,500

    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
    26  reviews
    from $496 
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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: TA-086-598-4512-01, GE-086-598-4512-01, 1390230750000

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    3  reviews
    from $641 
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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
    31  reviews
    from $409 
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  • Luxury Oceanfront Estate: Maunalua Bay Estate

    Oahu's Newest Luxury Estate
    Maunalua Bay Estate 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 estate is a modern ...
    Registration Number: TA-199-064-7808-01, GE-199-064-7808-01, 390260010000

    • 6 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    4  reviews
    from $3,140 
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