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Kailua Vacation Rentals

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    Travelers to Kailua are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 127 Rentals in Kailua
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Shangri La By The Sea - Stunning views with pool - ID1 / 21
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Book this lovely 3-bedroom, 2-bath vacation rental home in Kailua for a memorable beach getaway! Offering accommodations for 6 to 7 guests 6 to 7 guests with the 7th guest being a child, a spacious yard with outdoor amenities, and a prime location, just a leisurely walk from the sandy shores of...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront Hideaway1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
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    About this property
    Be prepared for absolute seclusion, with an electronic gate that opens and closes upon your arrival. Once inside the property, all you will hear are the birds, the sound of the surf pounding, and the rustle of the palm fronds from the many coconut trees on site. The house is right on the beach, and...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Mountain Views
    • Washer
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    • Grill
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A TASTE OF PARADISE LIVING: There is no better way to experience our island lifestyle than living oceanfront in beautiful Lanikai. This property is the perfect destination for capturing all that your hearts and minds conjure up when you dream about tropical paradise living. Your only limitation to...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This amazing studio is settled across the street from Kalama Beach in Kailua. Take a morning stroll to the white-sand beach with your coffee or head out to close-by, fun attractions such as snorkeling, kayaking, hiking, and more! Bike to Kailua Town for shopping, dining and exploring the charm...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    An open concept floor plan melds the two living areas, kitchen, dining area, and bar downstairs. All of the bedrooms are ensuite with 4 of the 5 offering ocean views. The seaside patio offers shade and a place to relax and enjoy the outdoors while taking in the glorious oceanviews all the way out...
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    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
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    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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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    BEACHFRONT 6BR/4.5BA Kailua family style with Pool1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Patio
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    • Waterfront
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note the homeowner lives on site, in a completely separate unit, and may be present during your stay* Your next Hawaiian getaway eagerly awaits at this 3-bedroom, 1-bath vacation rental house, just a 5 minute-drive from Kailua Beach. This home sleeps 5 guests and offers Koolau Mountain...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    About this property
    Walk to Kailua Beach or Kailua Town. Take a bus anywhere. This large 1 bedroom plus den has plenty of space and is so convenient! There's an outdoor shower to rinse off after the beach and a dedicated parking space. The minimum rental period is 30 days. Stay as long as you like. Each month is...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this home: Located in a great location in Kailua, this home is the perfect place to stay with friends or family! Recently built, this secondary-unit has private entry, an open shared space, comfortable sleeping area, and everything you need to cook for your group. As an ADA accessible home,...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Steps to Lanikai beach License #90_BB00181 / 13
    (34)Excellent
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    • Terrace
    • Air Conditioning
    • Balcony
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blossoms and palms welcome you as you enter the property. You are surrounded by shading trees and tropical flora. Just steps away is beautiful Lanikai Beach approximately 30 yards, just across the street. Lanikai is a quaint beachside community in Kailua on the island of Oahu.Our private,...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Balcony
    • Grill
    • Cable/satellite TV
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    • Patio
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Hawaiian vacation begins at this 4-bedroom, 2-bathroom vacation rental house in Kailua! Up to 8 guests can enjoy days soaking up some sun at the nearby beach, and their evenings relaxing with a refreshing tropical beverage on the lanai that spans the length of the house. If you'd rather be...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Hot Tub
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    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    Kailua, a relaxed lifestyle, and a Hawaiian home to relax and vacation with your family and friends. The beauty of Judys' Beachside Corner is that you can have one bedroom upstairs, or open up the downstairs and have an additional bedroom that can sleep 2-4 more guests. Upstairs is the master...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    • Private Yard
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kailua beach is about 1 mile from Kailua town. Kailua Guesthouse is located half-way between. It's about a 10-minute walk to the beach, a 10-minute walk to town. TheBus stop is about 300 feet from our front gate. My father acquired the property in 1947 and built our home here. My mother...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Private Yard
    • 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 967345
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Patio
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    E Komo Mai Private bedrooms are attached ' Ohana' to the main house with private entrance. Home provide a lovely the laid-back Kailua town and the beach lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along with beach...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • DVD Player
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    • Ocean Views
    • Internet Access
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will enjoy your one bedroom, king size bed, and fully furnished kitchen. Beautiful full service resort with a beautiful beach. Your ocean view room gives you views of Molokai Island. Watch the surfers, outriggers, kite surfing from your large balcony. Two world class golf courses close by. The...
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    Kailua, Oahu 96761
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch your worries melt away the moment you arrive at 'Lani Hale,' a 3-bedroom, 1-bathroom vacation rental home! Ideally situated among the peaceful streets of Kailua, this Hawaiian paradise boasts sleeping arrangements for 8, a furnished lanai, and an incredible location just 0.5 miles from Kalama...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, with a shared yard, and there may be other travelers present during your stay ** Say aloha to this quaint vacation rental studio in the beachside town of Kailua! Make the most of your romantic getaway with a myriad of...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Unforgettable Beachfront Oasis1 / 39
    (6)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
    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, with a shared yard, and there may be other travelers present during your stay ** Pack your bags and escape to the sleepy beach town of Kailua to stay at this 1-bedroom, 1-bathroom vacation rental apartment. Up to 4 lucky...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
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    • Terrace
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    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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    Kailua Flight and Weather Info
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    Daniel K. Inouye Intl Airport
    13.4 miles from Kailua
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