'Hale Kai' - Ocean Front/Beach Front Retreat - Private Tennis Court & Pool

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    $2,600 avg/night

    Hawaii> Kailua
    • 4 bedroom
    • 4 bathroom
    • Sleeps 10

    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.

    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: TA-126-531-7888-01,+GE-126-531-7888-01

    $2,600  avg/night
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    Marguerite S.
    Jul 02, 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.
    Jun 20, 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.
    Dec 18, 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.
    Thomas C.
    Mar 24, 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.
    Sandra C.
    Oct 01, 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!