Haleiwa Vacation Rentals

This beachfront plantation-style town is the largest community on Oahu's North Shore. Haleiwa offers plenty of dining and shopping opportunities while still retaining a laid-back and relaxed atmosphere. Vacation in Oahu's countryside and enjoy easy access to several world-famous surfing beaches, such as Sunset Beach and Waimea Bay. Haleiwa vacation rentals range from moderately priced homes and cottages to luxurious seaside retreats and villas. Find your perfect Haleiwa vacation rental below.

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  • The Verandah on Sunset Beach

    Hawaiian plantation living. The acre estate is located across from the world famous Sunset Beach, prime location. Located on a private road on...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Haleiwa
    3 night min stay9  reviews
    $400 per night
      Book Now
  • Tropical Waters Hawaii Garden View Home on Ke Iki Beach

    Honu Hale (Unit C) is a recently renovated traditional Hawaiian style plantation home found in Tropical Waters, a vacation rental retreat ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    4 night min stay1  reviews
    $418 per night
      Book Now
  • New Listing! Sunset Beach Home, steps from the beach

    Enjoy the best North Shore has to offer in private home, in a quiet and calm sunset beach neighborhood. You will be steps away from multiple ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    3 night min stay3  reviews
    $325 per night
      Book Now
  • August special!! Book 7 nights, get your 8th night FREE!! Spacious 3bed/2bath.

    Aloha! Our Hale (home) is located in one of ONLY ocean side communities on the sunset side of Haleiwa. We LOVE our neigborhood, it is one of ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    4 night min stay21  reviews
    $287 per night
      Book Now
  • North Shore Escape - Sunset Beach/Backyards Beach

    North Shore - Sunset Beach - Backyards Perfect Location for Triple Crown. Upper level of private home. 3 bedrooms -2 large bedrooms and 1 ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    4 night min stay1  reviews
    $264 per night
      Book Now
  • A Gem In A Peaceful North Shore Community.

    Private, detached, gorgeous, newly built, fully equipped, one bedroom guest house ready and waiting to be booked by you! Superb location! Short ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Haleiwa
    2 night min stay1  reviews
    $150 per night
      Book Now
  • 7 Mile Miracle! Perfect For Surfing, Diving And All Beach Activities.

    This 4 bed 2 1/2 bath home on the North shore has an amazing view of the beach and ocean from almost every window in the house. 4th bedroom is...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 9
    HI> Haleiwa
    5 night min stay8  reviews
    $565 per night
      Book Now
  • LOCATION, LOCATION, LOCATION!

    When you come to Oahu, you want to spend time at the best location. If you want to escape crowds, enjoy many fun and excellent restaurants and ...

    • 5 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> HALEIWA
    6 night min stay9  reviews
    $1,495 per night
      Book Now
  • Hillside Modern Ranch Style House

    Aloha, This is a no smoking property. We are offering our cozy 3 bedroom house sitting in the hills above Sunset Beach and Pipeline. Ideal for ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    hi> haleiwa
    5 night min stay19  reviews
    $300 per night
      Book Now
  • SPECTACULAR WAIMEA OCEANFRONT HOME!

    Enjoy this brand new oceanfront home, completed in 2015. The home sits on a half acre of oceanfront land which is fully landscaped. The property...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Haleiwa
    6 night min stay35  reviews
    $1,022 per night
      Book Now
    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Haleiwa
    3 night min stay1  reviews
    $195 per night
      Book Now
  • BEACHFRONT PARADISE ON THE SAND AT THE WORLD FAMOUS PIPELINE!

    *Longer minimum stay requirements may apply. Rates may vary depending on length of stay* Aloha and welcome to the beautiful Ehukai Hale located ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    HI> Haleiwa
    14 night min stay6  reviews
    $700 per night
      Book Now
  • Smokie Acre Blossoms - North Shore Oahu, Sunset Beach

    Capturing beautiful breezes and scents of a 2-acre Plumeria (Frangipani) flower farm surrounded by tropical fruit & foliage, owned & operated by ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    3 night min stay3  reviews
    $400 per night
      Book Now
  • Sunset Beach Spacious and Comfortable Apartment

    Comfortable and spacious upstairs two bedroom apartment with a third bedroom in the lower floor. Two living rooms, fully equipped large kitchen ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Haleiwa
    1 night min stay1  reviews
    $175 per night
      Book Now
  • Large Affordable 1 bedroom Apartment with Ocean Views-Walk to Beach & Surf

    Awaken to the cheerful songs of birds, gentle trade winds, and views of the ocean. This charming 1-bedroom apartment is nestled on a hill above ...

    • 2 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Haleiwa
    7 night min stay18  reviews
    $85 per night
      Book Now
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