Last Updated: November 05, 2026
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Pineapple Cottage is a peaceful vacation rental offering the perfect balance of privacy, comfort, amazing landscaping, and convenience on Maui’s North Shore. Tucked into a lush, country setting, this charming cottage on 2.5 acres, invites guests to slow down and experience the island in a more relaxed and authentic way, while still being just minutes from some of Maui’s most loved destinations. Inside, Pineapple Cottage features quality interiors designed for comfort and ease. The space is thoughtfully furnished, blending island style with a clean, welcoming aesthetic that makes it easy to feel at home. Natural light fills the cottage, creating a warm and calming atmosphere throughout. Step out onto the lanai and take in beautiful views that capture the essence of Maui. From here, guests can enjoy peaceful ocean views while listening to the gentle sounds of a nearby stream. The surrounding landscape is lush and well cared for, offering a sense of serenity and connection to nature. Whether enjoying morning coffee or unwinding in the evening, the lanai is a favorite spot to relax and take in the scenery. Despite its tranquil setting, Pineapple Cottage is just minutes away from excellent restaurants, local food spots, and some of the best experiences on the island. Hookipa Beach, known for its world-class windsurfing and surfing, Baldwin Beach’s golden sands, and the charm of Paia Town are all close by. Guests can enjoy hiking, shopping, and dining with ease, then return to the cottage for quiet evenings surrounded by natural beauty.. Pineapple Cottage enjoys a consistent 5-star rating. Ivy always welcomes you with her fabolous banana bread, and treats. |
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House Rules- No Pets, 4 guest maximun occupany, no large gathering, Age requirement booking 25, No smoking, on deck allowed, wash sand off feet, Quiet time 9PM to 8AM, check out 10am. Smoking allowed on deck No deeply scented body oils they are hard to get rid of the scent please (Request) Please remove shoes in cottage, no sandy feet (request) Enjoy your stay. We respect your privacy, but feel free to contact us with any needs, or information that you might need.
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 indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a deadbolt lock Property Registration Number 270350050000, BBPH2015/0011, GE-061-240-1152-01, TA-061-240-1152-01 A car is required for transportation to and from this property |
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| Season | Nightly | Weekly | Monthly | Min Nights | Additional person | Other fee |
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| Jan Jan-13-2027 Jan-31-2027 |
$350.00 | - | - | 7 | - | - |
| Feb-Mar Feb-01-2027 Mar-31-2027 |
$375.00 | - | - | 7 | - | - |
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To guarantee a reservation the requested deposit has to be paid by credit card (Visa or Master Card, Direct Bank Wire,Venmo) at the time of reservation has been made. 50% Deposit plus $150 cleaning fee. Rental rates do not include the 3% reservation fee with credit cards., or venmo.
Full payment is due 60 days (90 days Holiday Season) before arrival. Any abuse to the unit beyond “Normal Wear and Tear”, tenants are responsible for any additional cleaning charges. Cancellation Guest understands and acknowledges that the deposit is non-refundable in case of cancellation or reschedule received within 60 days (90 days Holiday Season) of arrival or after arrival date, payments will be retained. If the space can be re-rented, a pro-rata refund will be issued. TRIP INTERRUPTION/CANCELLATION insurance is available from independent providers and is STRONGLY recommended. The owner, in the event of Government Action, Natural Disaster, may cancel this reservation and liability shall be limited to the amount of monies paid to date on the account. Owner/agent shall not be liable for other expenses incurred such as plane tickets, pre paid rental car, etc. |
| Type | Price |
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| Cleaning Fee | $150.00 |
| Tax Rate | 18.00 % |
| Nearest Airport | Kahului Airport | 20 miles |
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| Nearest Bar | Colleens Haiku Center | 1 miles |
| Nearest Beach | 10 minutes Hookipa | - miles |
| Nearest Restaurant | Haiku Market Place | 1 miles |
Why it is Famous : Minutes to Hookipa Beach, Paia Town( old plantation town)
Facts About Destination : close to beaches and Haiku Town, and Paia Town
Area Information : Maui's Northshore, close to beaches, shops, places to eat
Why visit : Tired of condos, hotels, looking for a true island experience
How to reach : Car
Best time to visit : anytime
Transport system : Car
Precautions : you might like it
Life style culture : Laid back, getting back to true island living. Tropical, quiet, birds singing, Guest love it.
Languages spoken : English
Marina E.
We loved Pineapple Cottage. We are two type A personalty clean freaks and were in awe on how clean the entire house inside and out were. Steve and Ivy are very welcoming and have everything you need. They left fruit, snacks, chocolate, coffee and wine for us. Ivy’s banana bread with our morning coffee was the best way to start our day. We highly recommend Pineapple Cottage for a peaceful Hawaiian vacation.
Ann B.
The Pineapple Cottage is a well-appointed and peaceful place to stay with a lanai looking out into lush greenery and the ocean in the distance. Steve and Ivy were welcoming and available as needed. The location is away from the touristy areas and not far from great beaches. Mahalo for a great stay!
Colleen
Pineapple Cottage Visit
