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
  • 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

Leave a review:

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Comments

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Thank you for submitting your review. It will be processed shortly!

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

July 2026

S M T W T F S
      01 02 03 04
05 06 07 08 09 10 11
12 13 14 15 16 17
$1,601
 18
$1,601
19
$1,601
 20
$1,601
 21
$1,601
 22
$1,601
 23
$1,601
 24
$1,601
 25
$1,601
26
$1,601
 27
$1,601
 28
$1,601
 29
$1,601
 30
$1,601
 31
$1,601
  

August 2026

S M T W T F S
            01
$1,601
02
$1,601
 03
$1,601
 04
$1,601
 05
$1,601
 06
$1,601
 07
$1,601
 08
$1,601
09
$1,601
 10
$1,601
 11
$1,601
 12
$1,601
 13
$1,601
 14
$1,601
 15
$1,601
16
$1,601
 17
$1,601
 18
$1,601
 19
$1,601
 20
$1,601
 21
$1,601
 22
$1,601
23
$1,601
 24
$1,601
 25
$1,601
 26
$1,601
 27
$1,601
 28
$1,601
 29
$1,601
30
$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
 05
$1,601
06
$1,601
 07
$1,601
 08
$1,601
 09
$1,601
 10
$1,601
 11
$1,601
 12
$1,601
13
$1,601
 14
$1,601
 15
$1,601
 16
$1,601
 17
$1,601
 18
$1,601
 19
$1,601
20
$1,601
 21
$1,601
 22
$1,601
 23
$1,601
 24
$1,601
 25
$1,601
 26
$1,601
27
$1,601
 28
$1,601
 29
$1,601
 30
$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
 06
$1,601
 07
$1,601
 08
$1,601
 09
$1,601
 10
$1,601
11
$1,601
 12
$1,601
 13
$1,601
 14
$1,601
 15
$1,601
 16
$1,601
 17
$1,601
18
$1,601
 19
$1,601
 20
$1,601
 21
$1,601
 22
$1,601
 23
$1,601
 24
$1,601
25
$1,601
 26
$1,601
 27
$1,601
 28
$1,601
 29
$1,601
 30
$1,601
 31
$1,601

November 2026

S M T W T F S
01
$1,601
 02
$1,601
 03
$1,601
 04
$1,601
 05
$1,601
 06
$1,601
 07
$1,601
08
$1,601
 09
$1,601
 10
$1,601
 11
$8,750
 12
$10,052
 13
$10,045
 14
$10,173
15
$9,373
 16
$7,225
 17
$7,225
 18
$7,225
 19
$7,511
 20
$7,399
 21
$8,730
22
$9,524
 23
$9,967
 24
$10,481
 25
$10,801
 26
$11,543
 27
$10,382
 28
$8,866
29
$7,225
 30
$7,225
          

December 2026

S M T W T F S
    01
$7,225
 02
$7,225
 03
$7,225
 04
$7,225
 05
$7,225
06
$7,225
 07
$7,225
 08
$7,225
 09
$7,225
 10
$7,225
 11
$7,360
 12
$7,541
13
$7,557
 14
$7,225
 15
$7,225
 16
$7,225
 17
$7,731
 18
$9,915
 19
$10,060
20
$10,305
 21
$10,520
 22
$10,745
 23
$11,313
 24
$12,739
 25
$12,883
 26
$13,053
27
$14,571
 28
$14,658
 29
$14,721
 30
$14,755
 31
$16,338
    

January 2027

S M T W T F S
          01
$16,338
 02
$13,003
03
$11,771
 04
$11,767
 05
$8,508
 06
$8,759
 07
$9,269
 08
$8,936
 09
$9,824
10
$9,901
 11
$9,164
 12
$8,741
 13
$8,988
 14
$9,380
 15
$10,141
 16
$10,459
17
$10,269
 18
$9,882
 19
$8,928
 20
$9,052
 21
$9,496
 22
$10,090
 23
$10,173
24
$9,700
 25
$9,355
 26
$8,969
 27
$9,280
 28
$9,596
 29
$10,330
 30
$10,484
31
$9,518
            

February 2027

S M T W T F S
  01
$9,185
 02
$8,494
 03
$9,330
 04
$9,251
 05
$9,629
 06
$10,148
07
$8,923
 08
$8,748
 09
$7,931
 10
$9,647
 11
$9,943
 12
$11,082
 13
$11,614
14
$10,606
 15
$10,509
 16
$9,287
 17
$10,090
 18
$10,358
 19
$11,048
 20
$11,063
21
$9,999
 22
$9,834
 23
$8,815
 24
$9,080
 25
$9,345
 26
$10,365
 27
$10,230
28
$9,455
            

March 2027

S M T W T F S
  01
$9,502
 02
$8,922
 03
$8,849
 04
$9,211
 05
$10,492
 06
$10,580
07
$9,752
 08
$10,130
 09
$9,923
 10
$9,837
 11
$10,396
 12
$11,517
 13
$11,776
14
$10,556
 15
$10,689
 16
$10,033
 17
$9,519
 18
$9,692
 19
$10,286
 20
$10,518
21
$9,378
 22
$9,422
 23
$9,177
 24
$8,915
 25
$9,240
 26
$11,079
 27
$11,324
28
$10,302
 29
$9,164
 30
$8,997
 31
$8,895
      

April 2027

S M T W T F S
        01
$9,404
 02
$10,126
 03
$10,054
04
$9,095
 05
$8,713
 06
$8,734
 07
$8,717
 08
$9,074
 09
$9,523
 10
$9,102
11
$8,328
 12
$8,164
 13
$8,164
 14
$8,189
 15
$8,498
 16
$8,882
 17
$8,543
18
$8,164
 19
$8,164
 20
$8,164
 21
$8,164
 22
$8,164
 23
$8,164
 24
$8,164
25
$8,164
 26
$8,164
 27
$8,164
 28
$8,164
 29
$8,164
 30
$8,164
  

May 2027

S M T W T F S
            01
$8,164
02
$8,164
 03
$8,164
 04
$8,164
 05
$8,164
 06
$8,164
 07
$8,164
 08
$8,164
09
$8,164
 10
$8,164
 11
$8,164
 12
$8,164
 13
$8,164
 14
$8,393
 15
$8,518
16
$8,164
 17
$8,164
 18
$8,176
 19
$8,164
 20
$8,574
 21
$8,631
 22
$8,695
23
$8,167
 24
$8,355
 25
$8,569
 26
$8,164
 27
$8,600
 28
$9,863
 29
$9,923
30
$9,927
 31
$9,946
          

June 2027

S M T W T F S
    01
$8,648
 02
$8,188
 03
$8,808
 04
$8,746
 05
$8,802
06
$8,794
 07
$8,899
 08
$8,643
 09
$8,443
 10
$8,805
 11
$8,655
 12
$8,564
13
$8,604
 14
$8,643
 15
$8,199
 16
$8,565
 17
$8,947
 18
$9,499
 19
$9,648
20
$9,347
 21
$9,338
 22
$8,842
 23
$9,442
 24
$9,597
 25
$9,539
 26
$9,542
27
$9,423
 28
$9,355
 29
$8,860
 30
$9,467
      
    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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