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Kailua Luxury Holiday Homes

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    AU$3,107 Average
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    Travellers to Kailua are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in KailuaView all 128 rentals
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    8 Bedrooms, 9 Bathrooms, Sleeps 18 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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    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 3 April 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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    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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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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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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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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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 5 August 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 31 July 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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    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • 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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    BEACHFRONT 6BR/4.5BA Kailua family style with Pool1 / 28
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 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 9 April 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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Balcony
    • Parking
    • Washer
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one house off of the beach in central Kailua with private beach access 10 steps from your front door, Hale Ina Kalio will enchant you with it's breathtaking views, central yet private location and chic, Hawaii-modern decor. This house just completed a total renovation (2017) and is a brand...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    Shangri-La By The Sea - Tranquil, Gorgeous Stunning views with pool - ID1 / 21
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description Breath-taking views... luxurious details... this is Shangri-La by the sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua. The property is secluded with a...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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. Make stunning Mokulua Islands views the backdrop to your holiday photos at Lanikai Ocean View Villa. This welcoming vacation rental overlooks the eastern...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Grill
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home located can accommodate up to 12 people comfortably and can also be split in half to accommodate smaller parties. Located directly across the street from the Kailua Beach Park and Boat Launch, this modern rebuilt two-story home has a front main house consisting of 4 bedrooms, 4...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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