Pineapple Hill Kapalua Vacation Home


Rates: $1865 / night (avg.)
Bedrooms: 4
Bathrooms: 5
Bed types: KFQTQF (sleeps 8)
Reviews: 5.00 (from 46 reviews)
Nestled in the luxurious KAPALUA RESORT, this custom home is located in the prestigious gated community of Pineapple Hill. The 4-bedroom, 4.5 bath residence, encompassing over 3500 square feet, has 1 Master Suite, 3 Bedroom Suites (2nd Floor) and 2 smaller rooms that can be used as sleeping areas (1st Floor). All the bedrooms on the 2nd floor have individual baths. From one of the finest locations on Maui, you will enjoy world-class sunsets nightly. A state-of-the-art gourmet kitchen will also please any aspiring chefs.

The Family room, with travertine and marble floors and appointed with a large 50-inch HDTV and surround sound entertainment system, is located directly off the large gourmet kitchen, which features granite counter tops and stainless steel appliances. The master bedroom wing features it's own en suite bathroom with jetted tub, marble, double sinks, walk in shower and large walk in closet. The home also includes central A/C, wireless Internet, phone service, indoor/outdoor pocket doors, private yard with tiled hot tub and heated pool, large bedrooms with designer furniture and electronics, individual lanais furnished for your comfort, all while enjoying year-round ocean view sunsets overlooking the islands of Lanai and Molokai. Exotic art and elegant Asian accents create an interior that complements the natural surroundings. Amenities include two world-class golf courses, including the world-renowned Kapalua Plantation course, ranked #19 in Golf Digest’s Top 100 public courses in the U.S., a community Tennis Garden and pool, fine dining establishments and shopping. The Ritz-Carlton Maui is within walking distance. Kapalua also has miles of walking trails, from coastal to mountain.

A Complimentary Kapalua Resort shuttle service is available to guests. The shuttle will come right to your door, on-demand, and take you anywhere you want to go within the Kapalua Resort as well as to the Kapalua West Maui Airport.

PLUS DISCOUNTS ON GOLF AT BOTH KAPALUA GOLF COURSES ( PLANTATION COURSE / BAY COURSE )

TAT Tax ID # - 069-917-4912-01
GET Tax ID # - 069-917-4912-01
PERMIT NUMBER: STWM 2015/0002

Activities Can Also Be Arranged At a Discounted Price If Requested.


House Policies

1. No motorcycles, motor scooters, roller blades or skateboards are permitted inside gates.

2. All Owners and occupants shall exercise extreme care about causing or permitting noise that may disturb other Owners or occupants.

3. “Quiet Time” begins at 9 pm and ends at 8 am. Amplified sounds that are audible beyond the property boundaries of our home are prohibited. We recommend you move any “party” inside the home by 8 pm to avoid any noise problems with our neighbors. In the event the security guard is called out to our home to respond to a complaint by another Owner or occupant due to a violation of either of these rules, a $1,000 charge shall be deducted from your security deposit for each incident. (This penalty is charged to all Owners by the Homeowners Association for each complaint.

4. All vehicles shall be parked inside the property and shall not be parked on the street.

5. This property is a NON-SMOKING home and smoking is strickly prohibited in the home or near an open windows, or doorways. Any degree of disregard to this condition is subject to a minimum $500 charge for damages.

6. Guest agrees to abide by all House Rules of the property and the Owner, including, but not limited to, agreeing to cook only in areas designated for cooking and adhering to a no pets allowed policy.

7. Guest shall be liable for all acts of their family, friends, employees, and any other invitees otherwise on the property during the rental period.

8. Guest may not sublet or assign this agreement, nor shall Guest permit any use of the property without the prior approval of the property Owner, including, but not limited to, Swimming Pool, Hot Tub, Tennis Courts, Owner Cabana (where applicable) by other non-registered guest and more especially unsupervised children.

9. Guest understand that there are certain risk inherent to persons and property located near the Ocean, as well as at the Swimming Pool, Hot Tub, Tennis Courts, etc. Guest and other permitted persons shall under all circumstances use the Swimming Pool, Hot Tub, Tennis Courts, etc. at their own risk.


10. Guest acknowledges the need to use a Calling Card or Cellular Phone for all long distance calls.

11. Guest shall be responsible for returning all House and Gate Keys upon departure. Lost key charge is $50.

12. There will be no functions held at the property without prior written approval of the Owner. No parties or group gatherings other than registered guest shall occur.

13. Guest shall immediately notify the Owner of any Loss or Damage to the property.

14. Guest acknowledges that the Owner would not rent the property without the Guest acceptance of these conditions.

15. The property shall be in the same condition upon check-out as at check-in, other than normal usage that would be expected for a typical check-out cleaning. Damage or the need for additional cleaning may result in additional fee being incurred.

Registration Number: STWM20150002, 2420030270000, TA-069-917-4912-01, GE-069-917-4912-01

Pineapple Hill Kapalua Vacation Home Reviews



Ryan M.
January 2026
Enjoyed the many extras such as endless coffee, 2 bottles of wine, 3 boxes of Honolulu cookies and chilled bottled waters.


Andrew H.
January 2026
Great house great host


Ruth K.
December 2025
When you first walk into this beautiful home, the view is absolutely stunning! The owner provided Hawaiian themed treats and many other unexpected amenities. The kitchen was well stocked with everything you need to cook a family meal. Air conditioning, ceiling fans, laundry facilities, kitchen appliances and pool controllers all worked as expected. Everything was very clean. An unexpected bonus was the quality of the snorkeling equipment and other beach accessories provided. The neighborhood is peaceful and relaxing with several nice restaurants. One of the best things about this rental is the communication with the manager and the owner. They are helpful, welcoming and answer any questions very promptly. I really can’t say enough good things about this property and would definitely stay here again.


J M.
November 2025
The location was primo, and the house was lovely, but it showed its age. For example, the trash compactor wasn't working, the drapery wasn't fully hanging on the hinges, the carpets were spotted with stains, the main patio door was difficult to open, etc. That said, none of those inconveniences kept us from enjoying our stay.


DeAnne S.
September 2025
The house has a beautiful view of the ocean and spectacular sunsets. The host made sure that we had all the amenities that we needed. It was clean and well stocked with supplies. The house is close to the beach, Ritz Carlton, and has many restaurants nearby. The only downside was the pool needs updating and repairs. Great for groups or families.


Patricia W.
August 2025
Our family of 8 had a fabulous stay here. This house has more things than our own homes! 3 coffee makers?? One for espresso, one for pods and one for regular drip coffee and a built


Charity B.
June 2025
One of the few homes in Kapalua with a private pool and enough space for the whole family. Views are absolutely incredible, the neighborhood is super quiet, and the cherry on top is that the host is so kind and communicative. Thank you Alan for the wonderful stay. Looking forward to the next time!Mahalo….


Rebecca S.
May 2025
This owner was so kind and generous to us! He was very mindful about fragrances, detergents and soaps which he personally bought for us before our stay and exchanged things we requested for allergy friendliness and preferences


Olivia P.
March 2025
During our family vacation in Maui, we experienced an exceptional stay at a property that provided all the amenities we needed to feel comfortable away from home. The house’s prime location in Kapalua was convenient and hassle-free. The check-in process was seamless.One minor observation is that there is ongoing construction next door. However, this did not significantly impact our stay, as the noise level was minimal.We highly recommend this property to anyone visiting Kapalua, Maui. We appreciate your time and consideration in letting us stay on your beautiful home.Mahalo,Pash Family


Dale B.
February 2025
Alan was the perfect host. He accommodated more than we could ever need. The home was clean, comfortable, and well stocked. We’re very thankful to have had such a great place to stay.


Carmen S.
January 2025
Amazing Trip! Thank you for the extras to make our vacation feel like we were home.. Truly beautiful place. Seeing the whales from the house with binoculars was beyond fantastic!!


Trevor H.
October 2024
My friends and I booked Alan’s property for our yearly trip. The stay was flawless. Alan is an amazing host and had a fantastic property with everything you could want. His communications are impeccable and he really did think of everything. The house was great, well maintained and well stocked. The location was perfect as well. If you like golf it’s a no brainer. Plenty of activities and food options nearby. Easy access to grocery stores and the local Ritz Carlton Resort. I can’t imagine a better stay and I highly encourage you to stay at Alan’s home as well.


Sharon F.
February 2024
Beautiful view, nice arrangement of the floor plan. Our family of 8 loved everything about the house. Nice job to the homeowners and the property manager. We would definitely like to come back.


Amy S.
February 2024
My husband and I wanted to get away and the trip to Kapalua and the stay in Alan’s home was just what we needed! The house was comfortable, clean and very relaxing. We sat by the pool, watched the sun set every evening and were conveniently located near the beaches and golf courses. The area is very private and quiet. We look forward to returning to Alan’s beautiful home! We loved every minute of our time away! We felt very welcome and well taken care of! It was the perfect getaway!


Cynthia M.
February 2024
My husband and I traveled with our grown children and two young granddaughters. The host Alan was incredibly helpful and communicative prior to our stay. He went out of his way to accommodate and anticipate our needs for the young children and adults. He had nice cribs and high chairs waiting for us upon arrival along with many tasty treats. The home is very spacious and comfortable. Having a private pool and hot tub allowed for lots of fun family time. Overall it was a fabulous vacation.


adam L.
March 2023
This home is immaculate and the views are undeniable. You will not regret booking this property!


Lamar D.
December 2022
We could not have been more pleased with the property, communication and overall stay on our trip. Everything possible was available and having Alan and Russell help us with a late arrival due to the airlines and doing so in such a wonderful manner made a bad thing turn in to a good thing. We don't have enough kind words to say about the top notch property and service afforded us.


Brian G.
November 2022
If you are looking at this house just stop your search now and book it. The house, the location in Kapalua and Alan the owner all just exceeded our expectations. Upon our arrival, Alan met us at the house and welcomed us in. The house is well stocked and had everything we needed. Everything from beach gear, beach towels, tennis racquets, beach chairs, a wagon, they thought of everything. This was our third trip to Maui and this house raised the bar on our future visits. We are already looking to come back next year but with a smaller group and are planning on renting another one of Alan’s rentals.


Steve H.
November 2022
Did like the neighborhood and overall home but only one bed is larger than a full, making second and third bedroom awkward for couples. Bath did not drain in a couple bedrooms, even after property manager came and tried, mold in jacuzzi and pool, pool filter does not work. Kitchen was well stocked and although all appliances are old they worked.... lots of air cleaners set up throughout the unit but five of our group had moderate to severe allergies while staying at this home.


tony g.
April 2022
Home had everything you would need. Very lovely neighborhood and home.


Chris B.
April 2022
The owner made this the perfect stay. He thought of everything. The house had everything we needed. Perfect location, gym access, great location for daily walks. We will definitely try to stay again.


Paul S.
March 2022
Excellent


Sharon F.
November 2021
This was a once in a lifetime trip for my entire family. All photos were true to life. Alan was an excellent host. Available 24-7 if you need him. Home was furnished with everything plus anything you need. Beds very comfortable. Boxes of cookies and a bottle of champagne were at the house. Very memorable trip.


Jodie L.
October 2021
Two golf carts to go anywhere you need. You can take them to the Ritz, tennis, general store and close to the beach. The shuttle will take you anywhere else. House and linens very clean. If you need anything, owner will do anything he can to get it for you. We needed extra wine glasses and they showed up immediately. Well equipped kitchen with spices, sandwich bags of every size and foil. Neighborhood is secure and private. If you need to go outside of immediate area, Uber or Lyft are easy to get. Cannot say enough good things. DO IT!


Derek O.
October 2021
Our trip was in July 2021, but we can’t get it off our minds. This was the trip of a lifetime, and this house, along with Alan’s exquisite hospitality, made it a first class experience from start to finish. We arrived to a warm welcome and a house tour from Alan. The house was stocked with champagne, fresh fruit, chocolates, cookies, coffee, and even non-alcoholic champagne for the kiddos. The house has everything you need, from towels, to pool toys, to a telescope for nighttime stargazing. All bedrooms are cozy and comfy, and each person was provided with a robe and slippers (my kids loved this touch and felt so special!). We loved riding around in the golf carts and swimming in the private pool. The grounds are meticulously maintained and the gardener helped us get the fresh bananas from the backyard tree. All beach accessories are in the garage, including boogie boards and a wagon to carry it all. We had 7 people in our party from 12 years and up, and it was a dream vacation. At the last minute, we had the crazy idea to renew our vows on the property, and Alan went out of his way to make our ceremony a fairy tale experience. We can’t wait to go back, and we consider Alan a member of the family!


Barbara S.
October 2021
The house and surrounding area is beautiful. We were so comfortable in this lovely, spacious house. Alan is a GREAT “landlord”, everything was easy breezy. Three sister trip for three glorious weeks, paradise on earth. I highly recommend this property, you wont be sorry! We were greeted with fresh flowers and local fruit, champagne, plenty of towels, comfortable beds, and a well appointed kitchen. Absolutely everything we could need or want. The golf carts were great fun and the community pool is super nice and private, not to dismiss the nice pool and hot tub at the house. It was a joy!


Sharzad W.
May 2021
That’s what we called ourselves during our stay, Hawaii 7-0. Alan was incredible with all the communications before, during, and at departure. A lot of attention to details from fresh cut flowers, fruits, ice. Creams ... to tons of clean towels to fully stocked kitchen hand sanitizers and masks and even Hawaiian cookies and chocolate. Great AC, pool and spa were all great


Jason P.
April 2021
Our time at Pineapple Estates in Kapalua was absolutely incredible. No words can describe how beautiful, clean, friendly, spacious, relaxing, and overall life changing our stay was! The neighborhood, although filled with many houses, was set up so each house felt like they were on its own island! When walking around the neighborhood, we were able to see beautiful landscape and plants that were perfectly maintained. The walk was short to the beach as well as various tasty and fun restaurants. Overall, if you are going to Kapalua. Pineapple Hill Estates is the place to be. You cannot go wrong and it will make you vacation 300% better.


Susan M.
December 2020
We had a wonderful Thanksgiving week at Pineapple Hill. The home was exceptionally clean and very well stocked. Very large, spacious bedrooms and bathrooms. The here views are gorgeous! Alan responded immediately to any questions and even came over to fix the garbage disposal when it stopped working. Lots of pool toys, boogie boards and tennis equipment available in the garage, along with 2 golf carts to use on property. Very convenient location if planning to golf at Kapalua or explore the beaches and sights of west Maui. We highly recommend renting this house - we hope to be back again next year!


Henry B.
November 2019
Truly enjoyed our stay in Maui. Alan the owner and Russell the onsite manager were very helpful and responsive to all our needs. A wonderful home with all the right amenities for a three gen family. Hopefully we can come back sometime.


Ryan W.
July 2019
The pictures for this property don’t do it justice. Stayed here for 14 nights with my family. There were 7 people on our trip and the house was plenty big enough. Pool was great, especially for our 5 and 3 year olds. The views from the property are breathtaking both day and night. Kapalua is absolutely stunning and having the Ritz amenities including their shuttle service gave you the best of both worlds in terms of privacy and service. Shuttle usually shows up 5-10 minutes upon request and will take you anywhere in Kapalua. We used this service daily to head to the beach (3 minute drive). The property has more than everything you need to do the beach the right way, (beach chairs, umbrellas, boogie boards, snorkel gear, beach towels, cooler, etc.) Alan is the best manager we’ve ever dealt with. Quick to respond and come up with a solution. Also gave you complete privacy. The details he delivered upon arrival were impressive. Can’t say enough about this house. Loved our trip so much we are considering buying a property in the same neighborhood! Mahalo Alan, this trip was a special one... Mahalo Maui for showing our family how breathtakingly beautiful you are!


Diane A.
June 2019
Property manager was very responsive. House is large and accommodated our family of 6 with no problem. Very quiet neighborhood other than the pool construction going on next door. Kids enjoyed the ps2. Handy to have the golf carts but would have loved to take them out of the immediate pineapple hill neighborhood.


Jordan P.
April 2019
This home has a great location, lot's of restaurants, close to grocery shopping. There is a shuttle that can pick you up and take you to nearby beaches and the view was amazing!


Paul K.
September 2018
The perfect location, view and amenities made for a wonderful, comfortable and relaxing escape. We loved hanging out by the pool and enjoying the breathtaking view of the ocean and neighboring islands. Alan was responsive to our needs and even furnished us with fresh fruits, wines and suggestions for local activities and restaurants. To say the house is nice is an understatement. Plenty of bedroom options for all our needs, each with its own bathroom. Highly recommend.


Tyler O.
September 2018
We recently stayed with friends and family for our anniversary and Alan and his home were absolutely perfect. Leading up to our stay Alan was very quick to respond to any questions we had about the home, items we needed to bring, etc.... When we arrived he was there to personally great us and walk us through the house and provided us a list of restaurants and their numbers. The home itself exceeded expectations with wonderful views, an amazing pool and great entertaining spaces for our group. Would highly recommend Thanks Alan


Roseanna A.
February 2017
I was just vacationing at this luxurious home in January and it was absolutely amazing! Everyday when we woke up, we ventured on the pool patio and viewed the whales jumping as this view is the perfect location for it. We had so much space for all 8 guests as well as room for relaxing privately. I cannot say enough about Alan, who is the Manager for this property. Not only was he an amazing host, but he went out of his way to ensure our stay was an amazing experience. He let us use his golf carts, gave us any information we may need for our stay. He always ensured me that he was close by if I needed anything! One particular occasion was when I asked if he had binoculars and he went out of his way to get them for us! He also aloud us to use his go pro and is making us up a personal video of our stay as just a kind gesture! Please consider this your next vacation home. It truly was an unforgettable experience that me, my children, and family will NEVER forget!



February 2017
Me and my friends family stayed here for 3 weeks and couldn't be more happy that we picked this house! Allen was sooo wonderful and helpful on any needs or wants we had. He goes out of his way and does more then I've ever seen someone do! He even let us use a GoPro to use on our trip so we can record our time. And then he was making a video for us. The house was so big and beautiful, and everyday we sat and watched whales off our deck! The fresh flowers and treats he left was a nice touch as well. If you are looking for a place THIS is it! At the end of our trip he came to say his goodbyes and gave us presents which I won't say what it was.( a surprise) but even at that ,he didn't have to do but he did.I just want to Thank you Allen for making our trip a trip of a lifetime❤️ You Are The Best Host. thank you again.


Patti W.
July 2016
Our family of 10 (3 generations: 3 yrs. to seniors) rented this amazing, immaculate home for 2 weeks at the end of June/ beginning of July 2016. It's a one hour drive from Kahului Airport. Costco was our first stop near the airport, but there are several other groceries / markets closer to Pineapple Hill. Our host, Alan, was extremely responsive prior to our decision to rent, helping to make sure this home was the right fit for our family. He helped in advising/setting up a crib rental. On our arrival he provided a nice surprise as well as another one for our departure (I won't spoil that here!) The home was so well furnished and supplied w/ everything for a fun beach vacation: beach towels, boogy boards, snorkels, fins. Well-stocked kitchen / state of the art appliances / washer and dryer. Our family in various groupings covered the road to Hana, Haleakala, Black Rock, Wailea, Mama's Fish House, Kapalua golf, Old Lahaina Luau, scuba diving, snorkeling, spa day at nearby Ritz. The community shuttle bus will take you to the beach or into Kapalua for the general store, restaurants (or you could simply take the 2 golf carts supplied by Alan. The home ideally accommodates 8 and with flexibility/ easy going people: 10. Definitely a home to return to again and again.....


Bill B.
June 2016
We rented this home for 9 nights to attend our son's wedding at the nearby Ritz. We had 8 adults and 5 infants. We loved the home. It was exactly as presented in the pictures on this site. Alan was GREAT as a host and went out of his way to help make it a special time for us and remembered personal items that may have come up during our conversations. Gorgeous views....you may not want to leave. We will be back. Mahalo, Alan.


Jonathan W.
February 2016
We recently stayed at this house for 2 weeks over the New Year holiday with 9 members of our family. The views were spectacular and the house was exactly as described on the VRBO website. The owner of the property was a "pleaser," always taking extra steps to make sure our vacation was special. He added extra holiday decorations to the house, had the gardener bring fresh flowers and brought cookies to welcome us. As an added "above the call of duty," he retrieved a wedding ring left at the property and raced to the airport to deliver it to one of our family members before we departed. Now that is service! We had a wonderful and relaxing time at this property and would highly recommend it to others.


ashley h.
November 2015
We stayed for 9 nights with our family 10 people recently. From the moment we arrived the host Alan greeted us and made sure we had everything we needed, an amazing host and very easy to deal with. This was truly a world class property. We spent most time hanging out by the pool and enjoying the great views. It is very close to grocery store and also several beaches. We had a wonderful time and we look forward to our next stay.


Robert B.
November 2015
MY FAMILY I HAVE STAYED AT "SILVERSWORD" TWICE IN THE PAST TWO YEARS. OUR FIRST VISIT IN 2014 WAS FOR 13 NIGHTS. WE LOVED THE HOUSE, THE HOSTS, AND THE EXPERIENCE SO MUCH THAT IN 2015 WE STAYED 6 WEEKS. IT IS HARD TO PUT INTO WORDS WHAT A WONDERFUL TIME WE HAD. FIRST OFF, THE VIEW IS MULTI-MILLION DOLLAR WITH UNIMPEDED VIEWS OF BOTH THE ISLANDS OF LANA'I AS WELL AS MOLOKAI. SUNSETS WERE BREATHTAKING. SECONDLY, OUR HOST, ALAN, WAS TOP NOTCH. 100% RESPONSIVE. WE NEVER HAD A REQUEST HE COULD NOT FULFILL. WE TRULY ADOPTED HIM AS PART OF OUR FAMILY DURING OUR STAY. FINALLY, THE HOUSE FIT OUR NEEDS PERFECTLY. WE HAD PLENTY OF ROOM FOR THE SIX OF US TO SPREAD OUT, THE KITCHEN WAS WELL FURNISHED, FLAT SCREEN TVS WERE IN EVERY ROOM THOUGH WITH THE AWESOME VIEWS, WE FOUND WE RARELY TURNED THE TVS ON AND MOSTLY SPENT OUR TIME IN THE POOL AND HOTTUB. WE HAVE STAYED IN NUMEROUS HOMES IN MAUI. THIS WAS BY FAR THE BEST.


Linda G.
April 2014
Our family just spent 10 days in this house and what a wonderful place. There is nothing you need that it doesn't have. The manager goes out of his way to make your stay enjoyable. The owner was so thoughtful to our family helping us with our vacation above and beyond staying at the house. For golfers this location is great. Several courses to go to, with the shuttle to transport you. The kitchen was so well equiped we stayed in and cooked for most of our meals. Lot's of great walking paths, beautiful views and the greatest sunset everynight!

Note: Vacancy calendar is approximate. Visit the owner/manager's reservation site to verify your dates.

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