Kailua Shores Estate 5 Bedroom
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Resort-style pool area with loungers and umbrellas for ultimate relaxation in the sun.
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Aerial view of the stunning estate, showcasing its luxurious layout and lush surroundings.
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Kailua Shores Estate - USTA approved private Tennis Court nestled within tropical foliage for an exclusive playing experience.
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Formal living space in the beach house with cozy seating and panoramic ocean views.
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Stunning pool adjacent to the tennis house, ideal for cooling off after activities.
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Twilight Garden Path
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Spacious and inviting entrance surrounded by vibrant greenery.
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Twilight Tropical Gardens
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Twilight Outdoor Pool and Garden
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Stroll through enchanting grounds featuring a tranquil koi pond and tropical foliage.
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Beautifully landscaped pathways leading to serene and scenic areas of the estate.
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Living room overlooking a beautiful green garden
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Den and living area, offering a cozy space for relaxation or entertainment.
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Casual living area with comfortable seating, designed for unwinding and socializing.
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Beach house modern kitchen with high-end appliances and sleek countertops, perfect for preparing meals.
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Pool House chef’s kitchen and bar with modern appliances and a breakfast counter seating 3.
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Kitchen and dining space featuring modern appliances and an island with seating for 6.
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Tennis house dining area with seating for 6, ideal for enjoying meals with garden views.
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Dining area with a table that comfortably seats 6, featuring scenic views of the outdoors.
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Outdoor Dining area with seating for six, offering a cozy setting for al fresco meals amidst tropical surroundings.
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Tennis house guest bedroom featuring a king-size bed, elegant furnishings, and tranquil ambiance.
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Beach house spacious guest bedroom with a king-size bed, cozy seating, and garden vistas.
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Beach house spacious guest bedroom with a king-size bed, cozy seating, and garden vistas.
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Tennis house guest bedroom featuring a king-size bed, elegant furnishings, and tranquil ambiance.
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Pool house bedroom featuring a king-size bed and airy, coastal-inspired decor.
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Beach house modern amenities with a double vanity, large mirror, and spa-like finishes.
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Experience the estate’s tranquil beauty during sunset with expansive views.
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Expansive manicured lawns leading to breathtaking ocean views, perfect for outdoor relaxation.
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Twilight Panoramic View showcasing the estate's serene beauty as the evening sky.
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Twilight Palm Trees swaying gently under the enchanting colors of dusk.
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Private Pool at Kailua Shores Estate surrounded by lush greenery, offering a tranquil retreat at Kailua Shores Estate.
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Tranquil poolside retreat illuminated for serene nighttime relaxation.
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Perfect for day or night games amidst the serene estate grounds.
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Enjoy a match on the well-lit private tennis court, surrounded by tropical scenery.
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Comfortable seating by the private tennis court, perfect for a break between games.
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Play an evening match under the well-lit private tennis court.
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Stunning nighttime ambiance around the private tennis court.
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Shaded lounge chairs by the tennis court for spectators and post-game rest.
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Tennis court under glowing lights provides the perfect space for an evening match.
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Aerial view of the tennis court surrounded by lush tropical landscaping.
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Stunning sunset backdrop over a vibrant pool area creates a magical ambiance.
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.
Welcome to Kailua Shores Estate by Gather, one of Oahu’s most secluded and private beachfront estates. This expansive beachfront property on Kailua Beach offers all the amenities of a luxury resort, making it perfect for family reunions, a retreat with friends, or an intimate Hawaiian wedding. Featuring four newly remodeled homes surrounded by lush tropical landscaping, this estate creates a personal oasis for your dream Hawaii getaway.
What we love about Kailua Shores Estate:
* Prime Beachfront Location: Situated on land once cherished by Hawaiian royalty, this estate offers direct access to the white sands of Kailua Beach.
* Luxurious Resort Amenities: Enjoy a private pool, hot tub, chef’s kitchen, and professional- USTA tennis court with a practice wall, spinshot plus tennis ball launcher, basketball, and pickleball.
* Spacious Accommodations: Four separate homes, each with Cal King beds and en-suite baths, provide optimal comfort and privacy.
* Historical Charm: The original beach villa hosted celebrities like The Beatles, adding a touch of nostalgia and glamour to your stay.
* Versatile Gathering Spaces: Whether relaxing by the lily pond, hosting a barbecue, or enjoying cocktails on a lanai, this estate offers countless options for both relaxation and celebration.
The estate’s four homes—Main House, Tennis House, Beach House, and Pool House—are designed for both luxury and convenience. Each home features high ceilings, modern island-style furnishings, and glass doors that lead to private lanais. The Main House includes two bedrooms plus a convertible den, while the Tennis House and Beach House each offer two and three bedrooms, respectively. The Pool House is a cozy one-bedroom retreat, perfect for a honeymoon-style getaway.
The property’s chef’s kitchen is fully equipped for preparing gourmet meals, and the outdoor bar and BBQ area provide a fantastic space for entertaining. Spend your days lounging by the pool, playing a match on the USTA-approved tennis court with practice wall and Spinshot Plus tennis ball launcher, basketball and pickleball court and equipment, or simply soaking in the serene ambiance of the estate’s tropical gardens.
When you’re ready to explore, Kailua Beach is just a short drive away, as are the charming shops and restaurants of Kailua Town. Golf enthusiasts can choose from three nearby courses, and for a night out, the excitement of Waikiki and downtown Honolulu are within easy reach.
Kailua Shores Estate by Gather combines the privacy and space of a luxury residence with the amenities and service of a top-tier resort. Book your stay and create unforgettable memories in this idyllic Hawaii setting.
The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.
TA-098-284-1344-01
TMK 430130050000
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Memories of Kailua Shores Estate will last a lifetime! The setting is hard to beat, and all separate villas are truly comfortable, spacious and offered a lot of privacy! The place was incredibly tidy and well maintained. The owners ensured we had everything and on top of that, they greeted us with the most bountiful “Aloha Welcome Basket” and exquisite flowers. Their generosity was felt throughout our entire stay. The estate was well stocked and prepared, plentiful toys and games to play.
Everything from start to finish was just perfect. The home and property were wonderful and everything that we had hoped it would be. If we needed anything, someone was always there to help, but if we wanted private family time that was always there too. Wonderful spot! Very special indeed!
Beautiful Beachfront Estate!
by Claudia past guestA slice of private paradise!
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| Room | Beds | Amenities |
| Primary Bedroom |
Cal King (1)
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AC, Beach View, Lanai, Ocean View, Ensuite Bathroom |
| Guest Bedroom 2 |
Cal King (1)
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AC, Beach View, Lanai, Ocean View, Ensuite Bathroom |
| Guest Bedroom 3 |
King (1)
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AC, Beach View, Lanai, Ocean View, Ensuite Bathroom |
| Guest Bedroom 4 |
Cal King (1)
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AC, Beach View, Lanai, Ocean View, Ensuite Bathroom |
| Guest Bedroom 5 |
Cal King (1)
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AC, Beach View, Lanai, Ocean View, Ensuite Bathroom |
| Primary Ensuite | ||
| Guest Bedroom 2 Ensuite | ||
| Guest Bedroom 3 Ensuite | ||
| Guest Bedroom 4 Ensuite | ||
| Guest Bedroom 5 Ensuite |