Kailua Shores Estate 8 Bedroom

Kailua, HI 8 Bedrooms Vacation Rental

8 Beds 9 Baths Sleeps 18
Formal living space in the beach house with cozy seating and panoramic ocean views. Main House outdoor Dining area with seating for six, offering a cozy setting for al fresco meals amidst tropical surroundings.
Main House outdoor Dining area with seating for six, offering a cozy setting for al fresco meals amidst tropical surroundings.

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Rooms

  • bed icon

    Bedroom # 1

    Primary Bedroom

    1 Cal King

  • bed icon

    Bedroom # 2

    Guest Bedroom 2

    1 Cal King

  • bed icon

    Bedroom # 3

    Guest Bedroom 3

    1 King

  • bed icon

    Bedroom # 4

    Guest Bedroom 4

    1 Cal King

  • bed icon

    Bedroom # 5

    Guest Bedroom 5

    1 Cal King

  • bed icon

    Bedroom # 6

    Guest Bedroom 6

    1 Cal King

  • bed icon

    Bedroom # 7

    Guest Bedroom 7

    1 King

  • bed icon

    Bedroom # 8

    Guest Bedroom 8

    1 King

8 Beds 9 Baths Sleeps 18

Amenities

Private pool
Air conditioning
Beach Front
Ocean View

Reviews

  • Oct 06, 2021 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. Admin K
  • Jul 01, 2021 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! Joelle R

Description

Welcome to Kailua Shores Estate 8 Bedroom, one of Oahu’s most private and storied beachfront estates. Set on land once cherished by Hawaiian royalty, this 7,500-square-foot retreat spans four newly remodeled homes along the white sands of Kailua Beach. Designed for gatherings yet offering serene corners of solitude, the estate is ideal for multi-generational families, milestone celebrations, or retreats that balance leisure with luxury.

What You’ll Love About Kailua Shores Estate 8 Bedroom
* Prime beachfront location with direct access to Kailua Beach
* Private pool, hot tub, and USTA-certified tennis court with ball launcher
* Four distinct homes, each with Cal King or King suites and ensuite baths
* Historic villa where celebrities like The Beatles once stayed
* Expansive tropical gardens with lily pond, BBQ areas, and open lanais

Living & Dining
Each of the four residences—Main House, Tennis House, Beach House, and Pool House—has its own style, blending airy island architecture with contemporary furnishings. Multiple living areas feature vaulted ceilings, walls of windows, and seating that frames views of the ocean, pool, or gardens. Formal and casual dining rooms, both indoor and out, provide settings for family-style meals or sunset dinners.

Chef-Ready Kitchen
The estate’s kitchens are fully equipped with high-end appliances, espresso machines, dishware, and essentials for large-scale entertaining. The Main House offers a chef’s kitchen with generous counter space and an island perfect for gathering while meals are prepared. Outdoors, a bar and BBQ area extend the culinary experience to al fresco evenings.

Outdoor Oasis
Surrounding the estate are manicured lawns, koi ponds, and tropical gardens filled with palms and flowering plants. The private pool and hot tub are bordered by cushioned loungers, while multiple lanais provide shaded retreats. Active guests will appreciate the professional tennis court with practice wall, basketball, and pickleball setup, as well as direct beach access for kayaking, paddleboarding, or barefoot walks along the sand.

Sleeping Quarters
* Primary Suite – Cal King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 2 – Cal King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 3 – King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 4 – Cal King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 5 – Cal King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 6 – Cal King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 7 – King bed, ensuite bath, lanai, AC, ocean view
* Guest Suite 8 – King bed, ensuite bath, lanai, AC, ocean view
* Guest Bathroom 9 – Full bathroom

Extras
* Central air conditioning
* High-speed Wi-Fi
* Washer and dryer
* Smart TVs and cable
* Luxury linens and extra pillows/blankets
* Beach gear (chairs, umbrellas, mats, boogie boards, coolers)
* Toys and family-friendly amenities
* Private parking and secure entry
* Event-friendly spaces for gatherings

Nearby
Kailua Beach is just outside your door, while the boutiques, cafés, and markets of Kailua Town are minutes away. Three golf courses are nearby, and for nightlife or fine dining, Waikiki and downtown Honolulu are within a short drive. Hiking, snorkeling, horseback riding, and cultural sites are also easily accessible.

Good to Know
* The property is offered exclusively as a 30-day rental. The full monthly rate applies regardless of length of stay, as prorated rates are not available. Please inquire for details.
* Tax ID: TA-098-284-1344-01
* TMK: 430130050000

Reserve your dates at Kailua Shores Estate 8 Bedroom and experience the rare blend of beachfront seclusion, historic charm, and modern luxury.

Room

Beds

Primary Bedroom

Cal King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 2

Cal King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 3

King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 4

Cal King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 5

Cal King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 6

Cal King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 7

King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Guest Bedroom 8

King (1)

AC, Beach View, Lanai, Ocean View, Ensuite Bathroom

Primary Ensuite

full bathroom

Guest Bedroom 2 Ensuite

full bathroom

Guest Bedroom 3 Ensuite

full bathroom

Guest Bedroom 4 Ensuite

full bathroom

Guest Bedroom 5 Ensuite

full bathroom

Guest Bedroom 6 Ensuite

full bathroom

Guest Bedroom 7 Ensuite

full bathroom

Guest Bedroom 8 Ensuite

full bathroom

Guest Bathroom 9

full bathroom

Nearby Activities

  • Cycling
  • Fishing
  • Golfing
  • Hiking
  • Horseback riding
  • Museums
  • Scuba diving or Snorkeling
  • Shopping
  • Spa and wellness
  • Tennis
  • Watersports

Kitchen and Dining

  • BBQ
  • Blender
  • Coffee Maker
  • Dining Area
  • Dishes Utensils
  • Dishwasher
  • Espresso Machine
  • Freezer
  • Kettle
  • Kitchen
  • Kitchen Basics
  • Microwave
  • Oven
  • Refrigerator
  • Rice Cooker
  • Stove
  • Toaster

Amenities

  • Dryer
  • Essentials
  • Extra Pillows And Blankets
  • Hair Dryer
  • Iron
  • Linens
  • Parking space
  • Private Entrance
  • Safe
  • Shampoo
  • Washer
  • Wifi/Internet

Cleanliness

  • 24Hr Check-In
  • Self Check In / Check Out

Suitability

  • Air Conditioning
  • Bath Tub
  • Ceiling fans
  • Children Welcome
  • Free Parking
  • Hot Water
  • Minimum Age Limit
  • Pets Not Allowed
  • Smoking Not Allowed
  • Suitable For Events

Entertainment

  • Satellite or Cable TV
  • Television
  • Toys

Pool/Spa

  • Hot Tub
  • Private Pool

Internal Amenities

  • Beach Chairs
  • Beach Towels
  • Boogie Boards

Outdoor Amenities

  • Beach Bag
  • Beach Equipment Rentals Available ($)
  • Beach Mats
  • Beach Umbrella
  • Cooler - Ice Chest
  • Garden
  • Insulated Cooler Bag
  • Lanai/Balcony
  • Outdoor Shower
  • Private yard

Themes

  • Family
  • Luxury
  • Romantic

Car

  • Car Recommended

Location/Property Types

  • Beach Front
  • Beach View
  • Garden View
  • Near Ocean
  • Ocean View
  • Walk to Shops / Restaurants

Property Manager

  • 30 Day Properties
  • Claudia Evenschor
  • Mark LeRoy Hualalai

promos

  • Concierge

Leave a review:

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Comments

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Oct 06, 2021 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. Admin K
Jul 01, 2021 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! Joelle R

January 2026

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February 2026

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April 2026

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May 2026

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June 2026

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July 2026

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August 2026

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September 2026

S M T W T F S
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$3,002
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October 2026

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$3,002
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November 2026

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$5,336
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$9,571
          

December 2026

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$9,571
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$9,801
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$10,121
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$10,221
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$9,571
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$12,439
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$12,488
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$12,705
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$12,654
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$12,988
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$13,398
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$16,072
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$16,492
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$18,389
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$18,491
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$18,563
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$18,594
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$20,482
    
    Available     Unavailable  Check-In Only  Check-Out Only

Adults

Ages 18 or above

Children

Ages 2-17

Infants

Under 2

Pets

Bringing your pets?

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