Hale Kai Estate


Rates: $2937 / night (avg.)
Bedrooms: 4
Bathrooms: 4
Bed types: TQTQTKK (sleeps 10)
Reviews: 5.00 (from 15 reviews)
Welcome to Hale Kai, a stunning, private, gated historic Hawaiian estate located on nearly 3 acres of oceanfront property (500-foot frontage) directly on the calm waters of historic Keauhou Bay on the Big Island of Hawaii.

This main residence, designed by renowned Hawaiian architect Vladimir Ossipoff, includes a spacious open air living room, outside dining areas (seats 10), fully equipped kitchen and office. All share a breathtaking view of the bay and open ocean. The main residence includes a large master suite, which boasts its own private entrance and views of the bay. Adding to the extravagance of the property is the ocean side emerald blue tiled pool complete with lanai, pool side decking, ping-pong table and a guest suite. Located just behind the pool house are two separate guest hales each with their own bath and private entry.

The magic of this home truly lies in the authentic Hawaiian ambiance. From the cool sea breezes and astonishing views to the lush tropical gardens that stretches all the way to the water's edge to the estate's private dock, where guests can enter the calm waters of Keauhou Bay to snorkel and swim.

Enjoy a top-quality private tennis court nestled on the property.

The residence is fully furnished with resort amenities including: wi-fi, cable TV, BBQ, AC, security system, and ample parking. Onsite caretaker resides on property in a separate cottage.

Special Small Group Packages are available for 1-3 guests. Please contact host for information and pricing. Our rates are comparable to prime hotel rates. No resort fees, parking charges or tipping PLUS no privacy concerns.

Maximum of 8-10 guests per night.

Not Available for Weddings or Events.

Extended Stay Discount: For stays of 14 nights or more, a 10% discount will be applied for each night after the seventh. The first seven nights will be at the posted rate and any following nights after the seventh will receive a 10% discount per night.

Hawaii State Transient Accommodation ID # TA-126-531-7888-01
General Excise Tax ID # GE-126-531-7888-01
Short-Term Vacation Rental (STVR) # 19-353909
NUC Number: N/A - Property is a Permitted STVR

Permitted STVR Registration Number: GE-126-531-7888-01, TA-126-531-7888-01

Hale Kai Estate Reviews



Marguerite S.
July 2022
This home is beautiful and very well stocked. The grounds are lovely and peaceful. We loved being so close to the water and the beautiful dock for snorkeling and boat watching. It was very hard to leave the property to sight see because everything was just perfect at the house!


Steve N.
June 2022
This is the most amazing piece of property on Hawaii. The grounds are beautiful, when you think of a Hawaiian rainforest forest this is it, words can’t descrIbe it. You never need to leave the grounds to experience a Hawaiian vacation. The snorkeling is amazing, just as good if not better than all the areas we swam at, the ladder at the dock makes it easy in and out. The pool as well as all the houses are gorgeous. Everything you could ever need is there. I have stayed in homes on Hawaii and the other islands and this is as good as it gets. The entire staff and owner make sure your stay is perfect. I could go on forever, bottom line is, you will not be disappointed in your stay.


Robert T.
December 2021
This is a unique property with 270 degree water views, dock access into a bay/harbor (your snorkeling here is as good as any boat trip). With the pool, tennis court and ping pong on site, we didn’t need to leave (except for those wanting helicopter sight-seeing, etc.). It is a very well-appointed 1950s property that has been updated. Three acres of beautiful trees and flowers come with lizards and palmetto bugs, but this is to be expected. The hammock, plenty of outdoor seating for enjoying nature, the bay, and fabulous sunsets. We had a great thanksgiving feast with the fridge, freezer and cooking facilities more than sufficient for our large (dinner for 12) group. An on-site caretaker and attentive local support made our stay very easy.


Lawney F.
April 2021
I don't know that I've ever vacationed at a more beautiful oceanfront property. The ocean and bay views, sunsets and lush landscaping at Hale Kai make it a true paradise. Direct access to the bay & ocean via your own private dock for snorkeling, kayaking and paddle boarding is also a huge plus. It is a spacious, calming and magical property. The building layout is in a resort style with mostly separate buildings for each of the 4 (+) bedrooms. The kitchen and living area are also separated from direct access to any of the bedrooms. At first, this seemed a little odd, but after a couple nights it made perfect sense. If they choose to, everyone can have their own privacy and operate to their own schedule without disturbing others. The structures and fixtures could use a little TLC and/or upgrading here and there, and a "common" bathroom would be great, but everything is functional and there is a comfortable and traditional charm to the interior spaces across the board. Ben, the caretaker, was great and super responsive in addressing any minor issues or questions that we had during our 9-day visit. I can assure you that we will be back with more of our family members for a future visit ... this is one of the most beautiful and relaxing vacation venues imaginable.


Thomas C.
March 2020
We loved the big garden, with all the diffrent kinds of fruits in it. We loved the direct sea access. We loved the turtles and the mantas. Surrounding nice and green.


Pascal A.
February 2018
We were two families with 5 children in total from 9 to 14 yo. Everyone, adult and kid, was so happy to spend this time in Hale Kai, we didn't want to go out to visit the rest of the island. The garden and all the facilities are high standard. We enjoyed the sunsets, the pool, the tennis court and the hamac. Just 2 points could be improved. Firstly, the kitchen that is "old school" and the ocean access not very safe. The kitchen has not been upgraded for a while. The pantries, the range and the dishwasher could be changed. Moreover there were just enough set tables for the 9 people. The ocean access is very beautiful but not so convenient. One kid stepped on a sea urchin the first day and one adult who went to swim was stopped by someone on a canoe who told him it was not safe to swim in the bay because of the boat trafic. Except those 2 points, we were so happy to take advantage of that precious house, we would like to come back. We really spent heavenly vacations in that paradise. If you can offer that house, do it!


Sandra C.
October 2017
How to begin? There is so much to say, and only so much space. Hale Kai is a clean, well-kept, historic property, designed in the 1950’s by renowned architect Vladimir Ossipoff, on a breathtakingly beautiful, almost 3 acre property right on Keauhou Bay. The design of the main house allows you to feel both inside and outside at the same time, taking advantage of the cool breezes off the bay to keep the main living area comfortable on all but the warmest days. Hale Kai embodies the spirit of old Hawaii, with an emphasis on comfort, privacy, and a deep connection to nature. Looking out at the bay, you can certainly imagine why John Wayne chose this spot to marry his third wife. The grounds are immaculately kept and make you feel as if you are living in a botanic garden. The property has an abundance of fruit trees, including delicious starfruit, bananas, and mangoes, some of which we had the privilege of sampling. The arrangement of the rooms here allows for maximum privacy, with only the two guest hales sharing a wall. Each bedroom has its own very effective AC unit, which makes it very comfortable to sleep at night. There is a huge table on the lanai, perfect for our group to watch the sunset while eating dinner. In the mornings, we would have coffee there and watch the birds at the nearby feeders. As for activities, there is more than enough to do without ever leaving the property. You can swim, snorkel, or fish from the little dock on the property, explore the tide pools, swim in the pool, or play tennis. There are plenty of pool towels and the house is well stocked with everything you might want. I especially enjoyed the Hawaiian spa and bath amenities. I must point out that the service we received from everyone associated with this property was impressive and impeccable. When they say concierge service, they mean it! Krista was our initial point of contact and a wealth of information about the area. Krista also helped us arrange for a private chef to stock the house in advance and to prepare the most incredible meal to share with our guests. Our chef was Shirley, an absolute gem, and the four-course meal she prepared was one of the highlights of our trip. Derrick is the caretaker, and lives in a house at the back of the property. He let us have our space, but it is so convenient having him there to answer questions, or to fix any minor problem you might encounter. Krista, thank you and your staff for making our stay an amazing one!


Stacy B.
September 2017
FIRST TIME IN HAWAII AND WE COULDN'T HAVE ASKED FOR ANY PLACE MORE PERFECT TO STAY! WE HAD DAY TRIPS PLANNED AND SOME MORNINGS WE DIDNT WANT TO LEAVE THE HOUSE. WE PLAN TO RETURN!!!


Meredith H.
August 2017
I stayed at Hale Kai with 9 family member, 6 adults/3 kids, and could not have been more pleased with the experience. The online photos are beautiful, and they don't come close to doing it justice. The grounds are spectacular and the house was well appointed and comfortable. The layout of the property allows ample space for everyone to enjoy their own pursuit. At any given time, family members were playing tennis or ping pong or snorkeling or reading in a hammock. It provided a perfect balance of space and variety. Something for everyone and we rarely wanted to leave the property! I truly couldn't have loved this property more. In addition to the physical property, the support provided during the booking process and while at the house was great. The onsite caretaker was invisible until you needed him, and then he was there in seconds. I could come back to this property year after year and never get tired of it.


Jim S.
June 2017
Pool was enjoyed by the grand children and adults. Home is quaint and does show its age in certain areas, it is quite comfortable.

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

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