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.

Featured luxury Hawaii Kai vacation villas:

» Aloha Nalu » Hale Laulea » Hale Makana
» Makani Lani » Maunalua Sunset » Nani Wai
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  • Honolulu House w/Shared Pool by Koko Crater!

    There’s no better way to experience Oahu’s south shore than from this charming Honolulu vacation rental home. Ideal for a romantic retreat, this 1-bedroom, 1-bath home for 2 is a short stroll from the scenic Koko Crater trail system, 1 mile ...
    Registration Number: TA-038-936-9856-01, GE-03

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Honolulu
    30 night min stay5  reviews
    from $207 per night
      Book Now
  • 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, 13907

    • 1 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Honolulu
    30 night min stay1  reviews
    from $107 per night
      Book Now
  • Luxurious Tropical Getaway w/Salt Water Pool, AC & High Speed Wifi: Villa Luana

    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, 39081

    • 6 bedroom
    • 7 bathroom
    • Sleeps 14
    HI> Honolulu
    10 night min stay11  reviews
    from $2,625 per night
      Book Now
  • Luxurious Hawaiian Villa Oasis

    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 immaculate, ...
    Registration Number: TA-088-128-9216-01, GE-08

    • 4 bedroom
    • 4 bathroom
    • Sleeps 16
    HI> Honolulu
    3 night min stay18  reviews
    from $1,700 per night
      Book Now
  • 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
    HI> Honolulu
    30 night min stay1  reviews
    from $311 per night
      Book Now
  • Oceanfront Resort-like executive home AC, waterfalls, saltwater pool, spa

    **To see (50+) 5-star reviews for this property, please search listing ID 969030. This home SLEEPS A MAXIMUM OF 6 PEOPLE including children. Please provide names of all registered guests so our property manager can check you in. Unregistered ...
    Registration Number: TA-098-033-4592-01, 39092

    • 4 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Honolulu
    30 night min stay16  reviews
    from $1,025 per night
      Book Now
  • Luxurious & Private Modern Home w/Pool, AC & 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-01

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    HI> Honolulu
    10 night min stay11  reviews
    from $2,600 per night
      Book Now
  • Hawaiian Waterfront Home with Private Swimming Pool and Mountain Views

    This property is a legally established dwelling rented for periods of 30 consecutive days or more at any one time. Contact owner for more details. A Rare Private House in Hawaii! This family-friendly house is 'On the Water' with boat dock, ...
    Registration Number: TA-071-856-5376-01, 39032

    • 4 bedroom
    • 3 bathroom
    • Sleeps 10
    HI> Honolulu
    10 night min stay59  reviews
    from $599 per night
      Book Now
  • 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-13

    • 3 bedroom
    • 3 bathroom
    • Sleeps 10
    HI> Honolulu
    5 night min stay23  reviews
    from $795 per night
      Book Now
  • Honolulu Waterfront Oasis! 30 day rental

    True Hawaiiana at its best! Luxury 3 bedroom 2.5 bath waterfront home with pool, spa, tiki bar, 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 numerous...
    Registration Number: TA-092-645-7856-01, GE-09

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Honolulu
    28 night min stay28  reviews
    from $483 per night
      Book Now
  • 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-211-784-0896-01, GE-21

    • 5 bedroom
    • 4 bathroom
    • Sleeps 13
    HI> Honolulu
    7 night min stay5  reviews
    from $1,804 per night
      Book Now
  • Spectacular sea views

    MONTHLY RATE - $9000 To be in compliance with local regulations, this property is rented for periods of 30 consecutive days or more. Aloha and welcome! This lovely home is located in Portlock, one of Honolulu's most prestigious areas. The ...
    Registration Number: TA-065-699-8400-01, W0558

    • 5 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Honolulu
    30 night min stay52  reviews
    from $300 per night
      Book Now
  • Spring Special 15% Off Select Dates! Luxury Oceanfront Estate: Ocean House

    Last Minute Spring Special - 15% OFF Rates!! Promotion applies to booking dates NOW until April 30th This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Oahu's Newest Luxury EstateOcean House...
    Registration Number: TA-199-064-7808-01, GE-19

    • 6 bedroom
    • 7 bathroom
    • Sleeps 12
    HI> Honolulu
    7 night min stay4  reviews
    from $8,871 per night
      Book Now
  • Resort Like Experience with Ocean Views!

    Amazing ocean, marina and mountain views.. Enjoy the relaxing resort lifestyle, great unit high floor, remodeled (2018). Designer decorated, new flooring, upgraded appliances, kitchen and bathroom. Resort like amenities include fitness center,...
    Registration Number: TA-178-926-5920-01, GE-17

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Honolulu
    40 night min stay0  reviews
    from $138 per night
      Book Now
  • Luxury Home with Breath Taking Views in Hawaii Kai (Luxury area) 30 nights

    With breathtaking views of the beautiful Pacific Ocean, Koko Head, Hawaii Kai Marina, and Diamond Head, this mansion is perfectly situated above Kalama Valley. This 4BR, 4BA home is noteworthy for its impressive design elements including ...
    Registration Number: TA-136-130-3552-01, GE-13

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Honolulu
    30 night min stay0  reviews
    from $981 per night
      Book Now

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