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.

  • 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 ...
    Registration Number: 390240060000, GE-130-584-7808-02, TA-130-584-7808-01

    • 6 bedroom
    • 4 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    from $1,816 
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  • EXCLUSIVE EXECUTIVE HOME WITH FABULOUS 180o OCEAN VIEW.

    URGENT!! BARGAIN OPPORTUNITY! I have the month of January vacant! $7,600 for the month. ($280 per night) THAT'S A STEAL FOR THIS PROPERTY. HOP ON IT RIGHT NOW!! "Wow!" is the usual reaction of folks seeing the view from this traditional ...
    Registration Number: TA-166-425-8048-01, GE-166-425-8048-02, 390280160000

    • 4 bedroom
    • 3 bathroom
    • Sleeps 9
    Hawaii> Honolulu
    from $521 
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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: 390830520000, GE-060-165-9392-01, TA-060-165-9392-01

    • 0 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

    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: 390080100000, GE-177-601-5360-01, TA-177-601-5360-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $577 
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  • Aloha Nalu: Luxury family friendly Home w/Pool,AC,soaking tub,Diamond Head Views

    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: GE-019-941-5808-01, 390130060000, TA-019-941-5808-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    from $759 
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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: GE-060-531-3536-01, TA-060-531-3536-01, 390160020000

    • 6 bedroom
    • 7 bathroom
    • Sleeps 12
    Hawaii> Honolulu
    from $1,561 
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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
    from $145 
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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

    • 5 bedroom
    • 3 bathroom
    • Sleeps 10
    Hawaii> Honolulu
    from $1,036 
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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: GE-174-234-4192-01, TA-174-234-4192-01, 1390760570000

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    from $231 
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  • 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 ...
    Registration Number: 390080090100, TA-161-965-5168-01, GE-161-965-5168-01

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Honolulu
    from $205 
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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 $719 
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  • NEWLY REMODELED Mansion with Central A/C, Pool & Jacuzzi overlooking the Ocean

    *All rentals are made for a min period of 30 days with price reflecting the full period*

    Experience true luxury living with your own private salt water pool and Jacuzzi hot tub overlooking the ocean.

    Situated at the top of Kamehame...
    Registration Number: 391070860000, GE-021-991-0144-01, TA-021-991-0144-01

    • 5 bedroom
    • 5 bathroom
    • Sleeps 11
    Hawaii> Honolulu
    from $1,079 
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  • WATERFRONT! FISH FROM DOCK OR KAYAK TO THE OCEAN. MINUTES TO BEACH! LUXURY HOME

    Wrapped In A Silhouette Of Sea To Sky Views…Walls Of Glass Open To Dramatic Bold Sweeps Of Color. The Enchantment Begins As Your Eyes Feast On The Expansive Color Of Turquoise. The Main Living Spaces Flow Seamlessly To Embrace A Commercial ...
    Registration Number: 390080040066, TA-171-328-4608-01, GE-171-328-4608-01

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Honolulu
    from $526 
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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 $374 
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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 $259 
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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
    from $717 
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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 RATES AND STAYS 8083513885

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

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Honolulu
    from $748 
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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: TA-068-282-1120-01, GE-068-282-1120-01, 390950040000

    • 5 bedroom
    • 4 bathroom
    • Sleeps 13
    Hawaii> Honolulu
    from $770 
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