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Kailua Luxury Vacation Rentals

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    C$3,494 Average
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    Travellers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    20 Matching Rentals in KailuaView all 135 rentals
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    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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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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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description The Ohana Beachfront Villa is a 5-bedroom, 5.5 bathroom estate that offers a great view of Kailua Beach. You can enjoy the view from the ocean lanai and garden lanai, along with the landscaping. One of the best features of this home is a lagoon-style pavilion with tropical waterfalls...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
    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 plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is inspired in part by those...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Private Garden
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Lani Kai' means Ocean in the paradise in Hawaiian language, This historical original Lanikai Beach villa represents all the ALOHA spirit, open the windows in the morning, rising sun just coming out from the famous Mokes(Twin Island) in front of you. The Villa resides on the shimmering sands of...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lanikai By The Sea With front row seats to the ocean and the famous Mokulua Islands of Kailua, Lanikai Oceanside offers the best seats in the house. Newly renovated, this tropical chic, modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea,...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 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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    • 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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Washer
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the tranquil atmosphere of Maluhia whisk you into vacation mode. A favorite of many celebrities and families for the perfect, peaceful getaway, Maluhia is the definition of island contemporary. Its remodeled, modern interior features nearly 5,000 sq. ft. of living space. The villa also offers...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze! Brand new construction, built in 2017, this home features upgraded appliances and furnishings meticulously hand picked by local designer, Lotus Home Staging, highlighting many beautiful up-cycled, custom...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Unforgettable Beachfront Oasis1 / 39
    (8)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • 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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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • 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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    6 Bedrooms, 5 Bathrooms, Sleeps 14 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 14
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 between the three-bedroom Main House, and single dwelling Pool House and Studio Cottage, both with en-suites and kitchenettes, so privacy is...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home Away From Home Nestled in an intimate gated community, Kailua Beach House offers privacy, security and all the comforts you'd look for in an ideal vacation home. Featuring 4 bedrooms and 4 bathrooms on a single level, with an open floor plan that offers pool courtyard views from the kitchen...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    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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