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Kailua Luxury Vacation Rentals

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    C$2,961 Average
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    Travellers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    19 Matching Rentals in KailuaView all 127 rentals
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    8 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Waterfront
    • Parking
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the largest, most private and secluded Estates on the island of Oahu. A spectacular beachfront location-at Kailua Shores Estate with the comfort of a resort, consisting of separate houses, newly remodeled, set on extensive grounds featuring a pool, hot tub, tennis court, barbeque, plenty of...
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    Kailua, Oahu 96734
    Condo/Apartment - 8 Bedrooms, 9 Bathrooms, Sleeps 18
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    • Hot Tub
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Due to ongoing changes to the General Exercise Tax percentage in Hawaii, bookings may be subject to an adjustment or higher tax percentage. Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Fabulous Luxury 5 Bedroom Kailua Beachfront-Private Pool and Spa1 / 24
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 2, 2018
    Me and my husband ( grandma and grandpa) and our three adult children, their spouses and their five children just came home from a glorious time in this elegant yet comfortable...
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    About this property
    Three-quarter acre gated estate on Kailua Beach with pool, spa, beach vollyball and unobstructed sunrise ocean views from horizon to horizon. This Luxury Kailua Villa is a fabulous corner of paradise located on world famous Kailua Beach. This property is very secluded, located at the end of a white...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Over 3500 square feet of indoor living area, with TV, Stereo,, DVD, wireless internet, Gas BBQ and outdoor shower make this private, gated property a tropical retreat in paradise. Gracious living and tropical paradise are yours to enjoy in this magnificent Hawaiian vacation home. Designed for the...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Unforgettable Beachfront Oasis1 / 39
    (8)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2018
    We celebrated our 50th wedding anniversary with our family for two weeks in this beautiful home. We loved the ocean view from the living room, kitchen and master bedroom. We...
    Reviewed July 30, 2018
    Nice family or couples get away. Beds are comfy, pool while not huge did fine for the 12 of us. Beaches close by, easy to get into Waikiki or North Shore.... lots of Ahi Poke...
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    About this property
    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with a private pool, creating a very...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    BEACHFRONT 6BR/4.5BA Kailua family style with Pool1 / 28
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Patio
    • Grill
    • Waterfront
    • Outdoor Dining Area
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 8, 2013
    Wonderful location right on the beach and perfect home to celebrate my birthday with all 16 members of my family. Decor was a little dated but adequate. Loved being on the...
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    About this property
    Kailua Beach House is a casual, two-story 6 bedroom, 4.5 bath beachfront home with 5,000 square feet of living space. The 1/2 acre privacy-fenced property features a large, free-form swimming pool which has a poolside cabana with a shower and a built-in BBQ. The property decor features light...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr. Walker's inviting...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    42 feet from Kailua Beach. Available for Thanksgiving and until mid-December1 / 73
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    • Mountain Views
    • Children's Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 9, 2018
    We are certainly biased when it comes to ‘beach vacationing.’ We grew making family trips to Myrtle Beach, SC and later to Destin, FL for over 20 years. However, we must say...
    Reviewed May 31, 2015
    Our family got to spend a week in paradise in Dan's home. The view from the lanai is outstanding. Steps to the beach, all the beach and water toys one could ever hope for...
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    About this property
    Our home is located DIRECTLY on the Beach. Arguable the BEST BEACH, the BEST VIEWS, and on the BEST BEACH ACCESS in Hawaii. WONDERFULLY soft and manicured yard. LOTS of TEAK: lounge chairs, rocking chairs, porch swing, picnic tables, and accessories -THE HOUSE: Our home is tastefully decorated...
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    Location Information
    Kailua, Oahu 96734 2324
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lush landscape awaits you as you enter this gated tropical paradise tucked away beachside on a private lane, off Kailua Beach. Surround yourself with Hawaiian ambiance and the feeling of an amazing mini resort all to your own. Enter to this impressive 6-bedroom estate home surrounded by exotic...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This casual Kailua Beach house will transport and inspire you with its panoramic ocean views. All 3 bedrooms, living room and dining spaces offer incredible sites of blue seas and skies, while lush landscaping wraps you in privacy and scenery. This home has undergone a fresh renovation of kitchen,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful, covered lanai for...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Place in Paradise - Kailua Beach - Special Fall Rates Available.1 / 29
    (12)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Due to ongoing changes to the General Exercise Tax percentage in Hawaii, bookings may be subject to an adjustment or higher tax percentage. Located in the Lanikai Beach community, this beach house is perfect for a family vacation, getaway with friends, or a couples retreat. The villa is divided...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can be divided into three...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Mountain Views
    • Grill
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit...
    View all property information
    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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