Kailua Shores Estate 5 Bedroom

Kailua, HI 5 Bedrooms Vacation Rental

5 Beds 5 Baths Sleeps 10
Resort-style pool area with loungers and umbrellas for ultimate relaxation in the sun. Formal living space in the beach house with cozy seating and panoramic ocean views.
Formal living space in the beach house with cozy seating and panoramic ocean views.

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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

5 Beds 5 Baths Sleeps 10

Amenities

Private pool
Air conditioning
Beach Front
Mountain View

Reviews

  • Jul 10, 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
  • Mar 19, 2021 Wonderful spot! 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

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

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

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

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

Safety Features

  • Fire Extinguisher
  • First Aid Kit
  • Outdoor Lighting
  • Smoke Detector

Suitability

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

Entertainment

  • Satellite or Cable TV
  • Television

Pool/Spa

  • Private Pool

Internal Amenities

  • Beach Chairs
  • Beach Towels

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
  • Garden View
  • Mountain 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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Jul 10, 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
Mar 19, 2021 Wonderful spot! 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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$1,601

March 2026

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$1,601
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$1,601
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April 2026

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$1,601
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$1,601
    

May 2026

S M T W T F S
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$1,601
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June 2026

S M T W T F S
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
        

July 2026

S M T W T F S
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$1,601
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$1,601
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$1,601
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$1,601
05
$1,601
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$1,601
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$1,601
  

August 2026

S M T W T F S
            01
$1,601
02
$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
 29
$1,601
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$1,601
 31
$1,601
          

September 2026

S M T W T F S
    01
$1,601
 02
$1,601
 03
$1,601
 04
$1,601
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$1,601
06
$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
      

October 2026

S M T W T F S
        01
$1,601
 02
$1,601
 03
$1,601
04
$1,601
 05
$1,601
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$1,601
 07
$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601

November 2026

S M T W T F S
01
$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
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$1,601
 11
$8,750
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$10,052
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$10,045
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$10,173
15
$9,373
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$7,261
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$7,261
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$7,261
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$7,737
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$7,570
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$7,812
22
$9,331
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$9,608
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$10,360
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$10,633
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$11,669
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$11,290
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$9,134
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$7,769
 30
$7,769
          

December 2026

S M T W T F S
    01
$7,769
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$7,769
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$7,769
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$7,769
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$7,769
06
$7,769
 07
$7,769
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$7,769
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$7,769
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$7,769
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$8,538
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$8,205
13
$8,221
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$7,769
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$7,769
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$7,551
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$7,551
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$9,814
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$9,853
20
$10,024
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$10,272
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$10,542
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$10,877
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$12,751
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$13,048
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$13,388
27
$14,941
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$15,026
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$15,087
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$15,113
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$16,647
    
    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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