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Hawaii Kai Vacation Rentals

Hawaii Kai is one of the largest communities on Oahu's south shore. Here you will find a modest, but upscale selection of vacation rentals. 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, kayaking, canoe paddling, diving, fishing and boating.

  • Room in Hawaii Kai Marina Single family House Close to Beaches

    Hawaii Kai is a waterfront property developed by Kaiser back in the 60's. He envisioned this area as the playground for the Waikikians who would purchase these week end houses with boat docks for family fun. Little did he know that this area had ...

    4 Bedrooms, 4 Bathrooms, Sleeps 2

    HI>Honolulu

    95 USD - 115 USD

    nightly

    630 USD - 750 USD

    weekly

    2,200 USD - 2,800 USD

    monthly

  • Stunning Ocean, Mountain & Marina Views, Gorgeous Air Conditioned Guest House!

    Enjoy gorgeous unobstructed ocean, marina & mountain views from our luxurious 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, Ha...

    2 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

    150 USD - 230 USD

    nightly

    1,610 USD - 1,610 USD

    weekly

  • Panaoramic Ocean View Cottage

    Incredible view, very private setting, minutes from the beach with your own parking, washer/dryer and BBQ grill, very spacious kitchen with walk-in closet in both bedrooms, 2 flat screen TVs with Satellite TV, NFL Network, Netflix and Wifi. Each ...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Honolulu

    225 USD - 225 USD

    nightly

    1,500 USD - 1,500 USD

    weekly

    6,000 USD - 6,000 USD

    monthly

  • Oh My! It's Beautiful!

    Aloha! Welcome to Modern Hawaiian Living! New from top to bottom!!! Newly built and beautifully decorated with custom teak furniture from Bali and the most comfortable sofas, beds, linens and more! This home is equipped with everything you nee...

    2 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Honolulu

    335 USD - 455 USD

    nightly

    3,045 USD - 3,185 USD

    weekly

  • Family-friendly tropical hideaway. Everything you need to relax, enjoy Hawaii!

    W00416538-02 is our Hawaii tax number. Our home sleeps 8, has 3 bedrooms , 2 1/2-baths and is in quiet Hawaii Kai neighborhood. Split master with double sink, private shower and large jacuzzi tub, walk-in closet. Fully furnished with double bed i...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Honolulu

    375 USD - 700 USD

    nightly

    4,900 USD - 4,900 USD

    weekly

    8,000 USD - 13,000 USD

    monthly

  • Oceanfront Classic w/ all the Modern Comforts (~10% OFF ACTIVE DUTY MILITARY)

    'Oceanfront Classic' is an affordable 4 bedroom, 3 bath, oceanfront retreat. Walled and gated for security and privacy, Cat 5 wiring and Hi speed internet access for corporate retreats. Stunning Ocean views from living room, kitchen, and family ...

    4 Bedrooms, 3 Bathrooms, Sleeps 13

    HI>Honolulu

    550 USD - 750 USD

    nightly

    3,850 USD - 5,250 USD

    weekly

    14,850 USD - 16,200 USD

    monthly

  • Quiet Southeast Oahu 100' Oceanfront with Dock, Views Diamond Head to Koko Head

    Quiet and conveniently located at the tip of southeast Oahu's Niu Peninsula, yet close to bustling Waikiki and downtown Honolulu, this single level gated home features 100 feet of calm water oceanfront with a 180 degree view of Diamond Head to Kok...

    4 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Honolulu

    695 USD - 1,095 USD

    nightly

    4,865 USD - 7,665 USD

    weekly

  • Quiet Southeast Oahu 100' Oceanfront With Dock, Views Diamond Head To Koko Head

    For GUEST REVIEWS see duplicate listing #709768. Quiet and conveniently located at the tip of south Oahu's Niu Peninsula, yet close to downtown Honolulu and Waikiki, this single level gated home features 100 feet of calm water oceanfront with a 1...

    4 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Honolulu

    695 USD - 1,095 USD

    nightly

    4,865 USD - 7,665 USD

    weekly

  • Marina Front Luxury Oasis!!!

    Stay at the same home that 'DOG The Bounty Hunter' and his family once did. Dog, his son Leland, and other family & friends were our first guest. See why they chose OUR home for their family getaway! Welcome home to 'Lehua', a true Luxury Vacatio...

    5 Bedrooms, 3 Bathrooms, Sleeps 12

    HI>Honolulu

    750 USD - 850 USD

    nightly

    5,600 USD - 5,600 USD

    weekly

  • Kuapa Isle Hawaii Kai

    WATERFRONT. Spacious 4 bedroom, 3 full bath town home is the perfect island getaway with entertaining spaces on the back lanai looking over the water and mountains. Kitchen, living room, and indoor/outdoor dining areas are located on the first le...

    4 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Honolulu

  • Beautiful Beach House on the sand

    Charming, historic three bedroom, two bath beach front bungalow on Niu Beach. The original 1927 year old cottage was completely and lovingly remodeled in 2010, updating all electrical, plumbing, and appliances. This relaxed and stylish beach hou...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Honolulu

  • Beautiful Hawaii Kai Million Dollar Plus Home

    single family residence, upstairs, very private, large master bedroom, 2 bathrooms including shower and tub with jets, full kitchen with all modern appliances; enjoy relaxing and/or sun tanning with beautiful views (ocean and mountain) on the larg...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Honolulu

    1,500 USD - 1,500 USD

    weekly

    3,000 USD - 3,000 USD

    monthly

  • Luxurious Waterfront Oasis! Special Offer!

    True Hawaiiana at its best! Luxury 3 bedroom 2.5 bath waterfront home with pool, spa, tiki bar, fire pit, boat dock, two 60 inch flat screen TV's /DVD movie surround systems, Bose outdoor music near pool, granite, slate, and many more upgrade too ...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Honolulu

  • Koko Head Hale (House On Koko Head) - In Hawaii Kai (Hawai'i By The Sea)

    KOKO HEAD HALE (House on Koko Head) - in Hawaii Kai (Hawai'i by the Sea) NEWLY renovated 3 bedrooms, 2 baths fully furnished home use of high end materials such as Hawaiian hardwood flooring, solid cabinets, granite counter tops, buffet service co...

    3 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Honolulu

  • Heaven in Hawaii

    Located in Hawaii Kai our condo offers tropical landscaping with an awesome mountain and great ocean view. You will be able to relax and enjoy all the amenities of paradise in Hawaii or hit Waikiki for the night life and excitement. This unit ...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Honolulu

  • Steps to Beach Luxurious Condo

    This beautiful 3rd floor condo in an upscale high rise is surrounded by lush gardens, across from beach, walking only minutes away, private balcony, close to everything; private entrance from elevator, next to the Oahu Club Gym, Costco etc. Everyt...

    1 Bedrooms, 1 Bathrooms, Sleeps 4

    HI>Honolulu

  • AFFORDABLE Waterfront House in Honolulu, Hawaii

    A Rare Private House in Hawaii! This family-friendly house is 'On the Water' with boat dock, swimming pool, amazing ocean and mountain views! Four bedrooms(sleeps 10) with AC. It is the perfect Hawaiian Vacation home for a large family or multiple...

    4 Bedrooms, 2 Bathrooms, Sleeps 10

    HI>Honolulu