North Shore Oahu Gated Private Estate on lush 1 acre near Sunset Beach

Haleiwa, Hawaii

$419 avg/night

Overview

Bed

Bath

Private Vacation Home

Property Type

Max Sleeps

Description

Welcome to The Green Pineapple, an exquisite three-bedroom estate nestled in the tranquil, hilltop enclave of Pupukea on Oʻahu’s fabled North Shore. This distinguished two-story residence evokes the timeless allure of vintage Hawai‘i, gracefully reimagined with contemporary comfort and understated luxury.

Rich hardwood floors, high ceilings, and classic wainscoting set the tone for a serene island retreat. The home’s interiors are adorned with curated Hawaiian artwork and plush furnishings that blend sophistication with the relaxed rhythm of North Shore living.

The upper level features a spacious living area, a fully appointed kitchen, and three inviting bedrooms:

The Primary Suite offers a king bed, walk-in closet, deep soaking tub, and an oversized double shower.

The guest bedrooms—one king and one queen—share a beautifully appointed full bath.

A wet bar and game area provide an intimate setting for evening game of cards or chess and time to unwind..

With 400 Mbps high-speed internet and multiple workspaces, this home is ideally suited for guests seeking both tranquility and productivity.

Outdoors, verdant gardens and fruit-bearing trees (lychee, guava, citrus) surround covered lanais and patio spaces designed for relaxation. Enjoy an al fresco meal prepared on the gas grill, then refresh in the enclosed outdoor shower after a day along the shore. A covered garage and ample driveway parking accommodate multiple vehicles.

Additional Details
Mid-stay cleaning required; additional fees may apply

Main level accessible by stairs

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

***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

Rates exclude taxes, cleaning, and applicable fees

30-day minimum rental period in compliance with the City & County of Honolulu ordinances

Please inquire about adding the lower studio for 10 people MAX.

Hawaii Life Rentals, a locally owned and licensed real estate company, provides on-island assistance and personalized concierge services. A signed rental agreement is required within 48 hours of booking to confirm your reservation.

Experience the Essence of Classic Hawai‘i
At The Green Pineapple, tradition and tranquility meet in perfect harmony — a timeless retreat where vintage elegance and modern comfort define the North Shore experience.

Features
Map
Availability
Review

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
KITCHEN

Coffee/tea Maker Cookware/dishes/utensils Dishwasher Oven Stovetop
LAUNDRY

Laundry Facilities Washing Machine And Dryer
PARKING

Onsite Parking Onsite Parking Options Include A Garage
INTERNET

Free WiFi
OUTDOORS

Gas Grill Patio
BATHROOMS

2 Bathrooms Shower
LANGS SPOKEN

English
ENTERTAINMENT

Smart TV With Cable/satellite Service
LOCATION HIGHLIGHTS

Near The Sea
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

Check-in : 03:00 PM Check-out : 10:00 AM

No Wheelchair No smoking No pets Children allowed

Max occupancy : 6

Map

Availability

Review

Danita C.
Submitted Feb 6, 2025

Stayed Jan 18, 2025

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent a month in this wonderful home. We selected this location because of our desire to be on the North Shore side of Oahu, but not in areas quite as busy or more expensive. And we wanted a place that didn’t seem worn and showing signs of being a bit too close to the sea. My adult sons and I were spending a special time together and it was important we stayed in a location that looked peaceful and well kept - and large enough for the four for of us. The house was beautiful - the photos do not do it justice. It was quiet, cool, well furnished, and exceptionally clean. It had everything we needed including great, new appliances in the kitchen and laundry facilities. Coming from an area that it rapidly becoming urban (a concreate jungle) it was amazing to see so much actual grass and see the starts at night. All rooms had ceiling fans. The house isn’t airconditioned, so I was initially really scared. But the fans and floor plan keep the house cool – in fact some evenings were quite cold. The front of the house has a lanai which we loved sitting on in the cool mornings, and more importantly in the evening during sunset. Also, white the property is not on a beach (it is up hill quite a bit) you can still see the ocean. And the drive down to the beach had amazing views.The area was very, very quiet. It felt isolated from everyone, though in reality there were several homes around. The area was very dark in the evenings, which made for amazing star gazing but roads were very, very dark. That said, we never felt unsafe.
Joaquin C.
Submitted Apr 2, 2021

Stayed Dec 31, 1969

Amazing house, beautiful views during sunrise and sunset, lots of space, surrounded by nature with fruit trees in the property, no noise, and wonderful service from property manager.