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

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

Living Area
Entry to Studio
Studio arrangement
Living Area
Living Area

Reviews

9.8 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Outdoor Space
  • Parking available

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Other Space 1

1 Twin Bed, 1 King Bed and 1 Double Sofa Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Outdoor shower

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Kitchenette
Balcony
Separate dining area
Garden
Dining area

About this property

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

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)

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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Outdoor Space
Parking available

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House Rules

Check in after 3:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Property Registration Number 590220050000, TA-197-424-3328-01, GE-197-424-3328-01

About the neighborhood

Haleiwa

Located in Pupukea, a neighborhood in Haleiwa, this vacation home is in a rural area and near the beach. Sharks Cove and Pupukea Beach Park are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Turtle Bay Beach and James Campbell National Wildlife Refuge. Polynesian Cultural Center and Waimea Arboretum and Botanical Garden are also worth visiting. Scuba diving and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and hiking/biking trails nearby.
View more Vacation Homes in HaleiwaOpens in a new window
Map
Haleiwa, HI

What's nearby

  • Waimea Valley - 1 min drive - 0.8 km
  • Waimea Bay - 4 min drive - 3.8 km
  • Sharks Cove - 4 min drive - 3.8 km
  • Pupukea Beach Park - 4 min drive - 3.4 km
  • Ke Iki Beach - 4 min drive - 3.4 km

Getting around

  • Hālaulani / Leeward Community College Station - 45 min drive
  • Daniel K. Inouye Intl. Airport (HNL) - 67 min drive

Restaurants

  • ‪Ted's Bakery - ‬10 min drive
  • ‪Toa Luau - ‬10 min drive
  • ‪Kikoni Bar - ‬9 min drive
  • ‪Beach House by Roy Yamaguchi - ‬18 min drive
  • ‪Sunrise Shack Sharks Cove - ‬5 min drive

Frequently asked questions

Is Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat?

As of Apr 8, 2026, prices found for a 1-night stay for 2 adults at Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat on Apr 2, 2026 start from $411, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat?

Check-in begins at 3:00 PM.

What time is check-out at Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat?

Check-out is at 10:00 AM.

Where is Luxury | North Shore Oahu 4 Bed 4.5 Bath Private Beachfront Gated Retreat located?

Located in Pupukea, this vacation home is within a 15-minute walk of Waimea Valley and Waimea Waterfall. Pu'u o Mahuka Heiau State Monument and Three Tables Beach are also within 3 mi (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 2 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

A guest from MANHATTAN BEACH, CA

Quality Aloha Vacation Vibe

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.
Verified

10/10 Excellent

Amy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple paradise

Everything we could have hoped for and more. Such an amazing property and close to all things North Shore. Thank you!
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Debby B.

Absolitely PARADISE

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 !!!!!!!
Stayed 7 nights in Mar 2018
Archival

10/10 Excellent

Eva R.

Beautiful and peaceful

Perfect north shore experience away from the south shore bustle. Close to (20 min) Wheeler AFB for commissary grocery shopping and right down the street from Foodland for quick items. Check out the state park you pass everyday that looks over Waimea Valley and bay. Very close to the East coast to see the sunrise. Check out the sunset every night from the house deck for a partial view or any north shore beach. The house was equipped with everything we needed to make nightly meals and even baking and grilling. Thank you Green Pineapple for housing our family of 9. What a blessed 10 day visit.
Stayed 10 nights in Aug 2017
Verified

10/10 Excellent

Brittany F.

Amazing property, beautiful views, PERFECT location!

From the minute we arrived, we knew we booked the perfect property! Tucked up in the mountain, you're only a short drive (5 mins) to sharks cove, Waimea Bay, foodland/coffee beanery, and several food trucks! We are so glad we booked on the north shore - Haleiwa was only a 15 minute drive away as was the Dole plantation! We were close to everything we wanted to be without the hustle and bustle of Honolulu. The home is immaculate. Clean and updated, and the decor emulates a true, upscale Hawaiian vacation. Diana, the realtor, was in constant communication with us - making sure we were enjoying every minute of our stay. I am so glad our family booked this property! If I could give it 10 stars, I would!
Stayed 8 nights in Feb 2018
From a partner site

10/10 Excellent

EDUARDO Z.

home sweet home

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
Verified

10/10 Excellent

Michael B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for us

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!
Stayed 30 nights in Aug 2021
Verified

8/10 Good

Nathan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay on ohau

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.
Verified

10/10 Excellent

Glenn A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family getaway!

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.
Stayed 9 nights in Aug 2019
From a partner site

10/10 Excellent

Daniel R.

Hawaii Getaway

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!
From a partner site

10/10 Excellent

Cynthia K.

Best vacation ever

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
Stayed 7 nights in Apr 2019
From a partner site

10/10 Excellent

Elizabeth B.

Great Property!

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!
Stayed 20 nights in Feb 2019
Verified

10/10 Excellent

Darran B.

Outstanding

Thoroughly OUTSTANDING...Perfect location, georgious property, spotlessly clean and well maintained The property manager, Diana, is wonderfully helpful, incredibly cordial, and a total pleasure to work with
Verified

8/10 Good

Janine B.

A beautiful home with all the amenities of home.

We spent 6 lovely days at the Green Pineapple. We really appreciated the well stocked kitchen. The only thing we were short on were dishcloths and tea towels (with one of each). The beds were very comfortable and the rooms were clean and well looked after. The bathrooms were clean and the towels were lovely. It was much appreciated that there were beach chairs and towels to take to the beach. The location was perfect for exploring a variety of beaches. We loved that the Foodland was on our way home after each day's excursions as it made it easy for meal planning. If you stay here, make sure that you also find Ted's Bakery - they sure know what they are doing when it comes to pleasing your palette. This home was immaculate and we were a bit nervous having our children with us. The welcome book was very clear about the do's and don'ts. It was a little off putting that we were told that our children could not colour or do crafts at the table. Our children aren't into arts and crafts as they are 11 and 13 year old boys but reading that comment in the welcome book made it hard for us to relax completely. This house is better suited to families without children. Our only complaint was the yard. Our children were eager to play soccer and frisbee in their down time but they had to be careful about stepping in dog doodoo. Unfortunately someone's dog was using the grass to do their business. We would definitely return and we must point out that their reading materials were fantastic. Sincerely, Janine
Stayed 6 nights in Dec 2017
Archival

10/10 Excellent

Raymond T.

AMAZING

This property was immaculate and smelled so clean on our arrival. The house and grounds are so beautiful and well kept. The interior is well decorated, the beds are comfortable, the linens are soft and clean, there are plenty of towels for the bath and the beach, the kitchen is perfect for preparing meals and eating in, the master bathroom is amazing, and there's always a breeze to keep you cool. We had a 9 adults and and one baby in our group. We rented the house and the studio downstairs, so we had plenty of private space and room to hang out, eat, and play games. The shower outside was great for us to rinse off after the beach. The covered porch was great to hang out on too. The location is close to the highway, Foodland, and beaches. Our agent, Diana was responsive, courteous, and helpful. We will definitely return to the Green Pineapple when we come back to the North Shore area.
Stayed 8 nights in Jun 2017
Archival

10/10 Excellent

Diana N.

Best stay-cation ever!!

This house was the best get-away that we could have ever imagined.. If you want an immaculate, well appointed and quiet home to enjoy your North Shore experience, this house is the place. The whole house has a cozy feel, every room is charming and has everything you need. Outside hot/cold shower was a bonus for days coming in from the beach and hikes. Outdoor grill and table was the perfect setting for evening grilling surrounded by the tropical landscaped acre lot. Love, loved, the deep soaking tub in the master bedroom and the gas stove in the large open kitchen! There is a fun game table with chess and other card games available that brought out our inner-child.. WIFI signal is strong in every room. We left refreshed with amazing memories.. Will definitely be back again~
Stayed 3 nights in Feb 2017
Archival

10/10 Excellent

MARC L.

Absolutely Stunning!

We could not be more satisfied with our stay. The property was flawlessly decorated, immaculate, and clean, and the grounds were well-maintained. This property feels as if it was designed for travelers' enjoyment, unlike some properties that feel like someone lives there most of the time, and they're just gone while you're staying there. Each room was superb. The kitchen was perfect. The neighborhood is super quiet. I would recommend this property to anyone wishing to visit the North Shore of Oahu. It's only a 5 minute drive down to the beach, but provides a soothing sanctuary from the crowds at the coast.
Stayed 18 nights in Jan 2017
Archival

10/10 Excellent

Danae P.

Beautiful Hawaii

The home was beautiful and well-kept. Everything we could have asked for and more. Such a pleasure to deal with. Thank you for the wonderful vacation!
Stayed 5 nights in Aug 2016

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