Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat

Haleiwa, Hawaii
$521 avg/night
Bed 3

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Welcome to The Green Pineapple, an exquisite three-bedroom estate with an attached studio apartment, situated in the serene, milder temperature, hilltop community of Pupukea on Oʻahu’s North Shore. This distinguished two-story residence embodies the grace and character of vintage Hawai‘i, enhanced by modern amenities and fine finishes throughout.

Property Overview |
Designed with a sophisticated balance of comfort and style, the estate features hardwood floors, wainscoting, high ceilings, and curated Hawaiian artwork. The result is a luxurious retreat that captures the essence of island living in a refined and tranquil setting.

The upper level includes:

Primary Suite with a king bed, walk-in closet, deep soaking tub, and oversized double shower

Second bedroom with a king bed

Third bedroom with a queen bed

A shared full guest bathroom

Elegant living and dining areas, and a fully appointed kitchen

Game area and wet bar — ideal for evening entertainment or quiet relaxation

High-speed 400 Mbps Wi-Fi and ample workspace make this residence particularly well-suited for guests requiring a professional environment while working remotely.

Studio Apartment
The lower level offers a fully equipped studio apartment with a kitchenette, full bath, and private entry. The open-concept suite accommodates up to four guests with a king bed, sofa sleeper, and extra-long twin punee bed. The studio and main residence are offered together as a single rental to ensure exclusivity and privacy.

Outdoor Features
Expansive covered lanais on both levels provide serene outdoor living spaces surrounded by lush tropical foliage and fruit trees (lychee, guava, citrus). The property also features an enclosed outdoor shower for convenience after beach outings, a gas BBQ grill, and a two-car covered garage with ample driveway parking for additional vehicles.

Additional Information
Mid-stay cleaning service required

Main residence accessible via stairs

No check-ins permitted on major holidays (Christmas, New Year’s Day, Easter, Thanksgiving)

Maximum occupancy: 10 guests (6 in main home, 4 in studio)

***DISCLOSURE 9/28/26: Home has been listed for sale, and guests may be required to permit showings with 48 hours notice.

TA#197-424-3328-01

Long-term rental options are available upon request.
Rates do not include taxes, cleaning, or applicable fees. Guests are required to sign a rental agreement within 48 hours of booking to confirm the reservation.

Experience Classic Hawai‘i
At The Green Pineapple, vintage island elegance meets modern comfort. This distinguished estate offers an ideal setting for guests seeking privacy, sophistication, and the authentic beauty of Oʻahu’s North Shore.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Sofa Bed
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Garden Gas Grill
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Golf Nearby Golfing On Site Hiking Nearby Hiking/biking Trails Nearby Horse Riding Nearby Marina Nearby Snorkeling Nearby Tennis On Site Windsurfing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • LOCATION HIGHLIGHTS

    In A Rural Location Near A Hospital Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Cobblestone Flooring In Public Areas Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • A guest from MAN....

    Submitted Apr 1, 2026

    Stayed Mar 1, 2026

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We felt comfortable and secure in the Green Pineapple due to the quality accommodations and physical location, during historical Hawaiian rainfall and flooding at lower elevations of Pupukea. We appreciated Hawaii Life's attentive, quality management and service for a quality, luxury property.

  • EDUARDO Z.

    Submitted May 3, 2024

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything works great out here.Fantastic place.Tks Diana for all of your support.Aloha

  • Michael B.

    Submitted Sep 1, 2021

    Stayed Aug 1, 2021

    The Green Pineapple Estate was a perfect place for my wife and I, our two daughters and my wife's parents to stay. The house itself provided the perfect balance between privacy and togetherness. The north shore location was ideal for us. We hope to stay there again someday!

  • Nathan C.

    Submitted Jan 22, 2020

    Stayed Dec 31, 1969

    We loved our time in Hawaii and this property was very pleasant. We did have a prolonged power outage of around 24 hours which made being so far from the beach a little more difficult but certainly outside the control of the property owners. It is a very clean and very spacious house. Great for a larger group.

  • Glenn A.

    Submitted Aug 19, 2019

    Stayed Aug 9, 2019

    Our family of 5 rented the green pineapple for 9 nights and had an excellent time. The north shore is away from all the hustle and bustle of Honolulu and there are so many things to do within a 15 minute drive. Never a dull moment! The house is beautiful, with plenty of space for a family of five. Our two girls shared the guest room king bed while my son had the third bedroom. Plenty of room for all! The kitchen is well equipped with high end appliances. We enjoyed breakfast and, often, lunch at the property. The property is conveniently located to the local Foodland store, only about 2 miles. The property itself is very well maintained and safe, with a gated fence. The property manager, Diana, was very responsive to all our needs. In all, we had a great stay and would definitely come back.

  • Daniel R.

    Submitted Jul 31, 2019

    Stayed Dec 31, 1969

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I stayed here with my family of 6. The house was spectacular and the property secluded enough to give you privacy yet all the sights and sounds of Hawaii. The downstairs worked as a separate home for my daughter and her Husband. Diane was quick with any questions or assistance! Loved the sounds at night and the views. The home is definitely a must if you have a group of people and enjoy cooking. The kitchen is outstanding. Highly recommend this home!

  • Amy B.

    Submitted Jul 13, 2019

    Stayed Jul 2, 2019

    Everything we could have hoped for and more. Such an amazing property and close to all things North Shore. Thank you!

  • Cynthia K.

    Submitted May 1, 2019

    Stayed Apr 3, 2019

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: where to start arrived totally amazed at the house. when i had a problem Diana was right there to help. it was a great experience for me and my family. thank you very muck

  • Elizabeth B.

    Submitted Mar 13, 2019

    Stayed Feb 17, 2019

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I stayed here with two of my coworkers for 3 weeks while on business. The house had plenty of room for us to spread out and have our own space and had all the amenities we needed to make it feel like home for 3 weeks. It's located a couple miles from the beaches up in the hills which is nice because you're away from the busyness of the North Shore but still aren't far away if you want that experience. This home is well kept and clean. Definitely booking this property again when we are back for work!

  • Debby B.

    Submitted Apr 16, 2018

    Stayed Mar 28, 2018

    Fun for the whole family and plenty of room for everyone. We LOVED this home away from home, gourmet kitchen, beautiful bedrooms, master suite that invites you to stay forever. A view of the valley and the ocean, just a short drive to the North Shore and all of it's wonders. I have already recommended this wonderful home to my family and friends. You won't be disappointed !!!!!!!

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Total

Includes taxes and fees
$521+
View details