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Holiday Rentals near Lanikai Pillboxes

382 Kaelepulu Dr, Aalapapa Drive, Kailua, Oahu, Hawaii 96734-3312
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    Travellers to Kailua are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 79 Rentals in Kailua
    Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $2201 / 26
    (4)Very good
    4.4 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Plantation Charm in Kailua1 / 30
    (5)Very good
    2.8 kilometres from Lanikai Pillboxes
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (29)Excellent
    1.5 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Nancy's Kailua Cottage Makai1 / 32
    (8)Excellent
    1.4 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close...
    Reviewed 12 March 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    About this property
    Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    4.4 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2019
    This place was wonderful. Quiet and lovely beachfront home. We stayed in the Mountain Suite and took advantage of the saltwater pool with the waterfalls. The only issue was the...
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    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period... Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and full size...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOVE RENTALS - FIND YOUR BLISS Ocean-themed studio. Bike to Kailua Town shops, dining, or to the beach! Safe, quiet neighborhood allows for a great experience on your vacation. This studio has a stove top, rice cooker, coffee maker, refrigerator and all things you need to make at-home meals. Relax...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Kailua Beach Aloha Cottage1 / 13
    (1)Average
    3.3 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2018
    First up Ryan said he wanted us to have a 5 star experience in his messaging to me. We booked this for first 3 nights of 2018. Kailua is a great area. You did get was stated but...
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    About this property
    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Sheffield Studio  Walk to Kailua Beach or Town1 / 7
    (3)Very good
    1.9 kilometres from Lanikai Pillboxes
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2017
    I returned to Sheffield Studio in Aug 2017 with my husband for an 11 night stay and it was very much as remembered from my previous visit in 2014. The location is great, you...
    Reviewed 1 February 2017
    This studio really fulfilled all the expectations that me and my wife have when we are out travelling and searching for good accomodation. Rachel and her husband are very...
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    About this property
    Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The Ginger Studio has free off...
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    Kailua, Oahu
    Private Room - 1 Bathroom, Sleeps 2
    1.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this Charming Cottage in beautiful Lanikai. Enjoy the convenience of relaxing on a beautiful Short walk to the beach nightly, and get lost in the comforts of a cozy home with an efficiency kitchen and your own washer and dryer in the home. There is One split AC unit. Property has a Large...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Lanikai Cottage1 / 13
    (3)Very good
    1.1 kilometres from Lanikai Pillboxes
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2019
    The cottage is beautifully updated and is fully stocked with everything you need.It is very spacious, and I love the white decor!The beach chairs are a bit old; the straps...
    Reviewed 9 July 2015
    I enjoyed our stay in Lanikai, the cottage was perfect. The fully stocked kitchen made making tea to cooking a breeze. It was so easy to get to the beach and easy to find hikes...
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    About this property
    This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,...
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    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kailua, Cozy, Spacious Duplex Home, carport, yard, 30 day min.1 / 20
    (3)Excellent
    3.3 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2017
    We enjoyed our recent stay at the duplex home. The living area is very spacious with a fully stocked kitchen. Owner has done an exceptional job with the lighting and ventilation...
    Reviewed 30 August 2017
    Great place with very helpful hosts. Can't wait to go back! Near a number of excellent beaches and places to see.
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    About this property
    This 850 sq ft duplex consists of a very spacious living room with a vaulted ceiling, 1 bedroom, 1 full bath and a full kitchen with oven. All the areas come with ceiling fans and the home is indirectly ventilated with a whole house fan. The bedroom has a queen bed and comfortably sleeps two...
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    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Kailua, Cozy, 2 bedroom, duplex home, carport, yard, 30 day min1 / 22
    (3)Excellent
    3.3 kilometres from Lanikai Pillboxes
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2018
    We loved the beaches that are close to this quaint duplex. Everything you need for the beach is provided - boogie boards, sand toys, mats, umbrellas, towels, cooler. We also...
    Reviewed 30 December 2017
    We enjoyed our stay at this place. J &R were great with suggestions and making us feel at home. The location was great, near 2 of the best beaches in Hawaii. When I was told...
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    About this property
    This 850 sq ft duplex consists of a master bedroom with a queen bed and a huge walk-in closet. Access to the full bathroom is through the master bedroom. The other bedroom also has a queen bed. All the areas come with ceiling fans and the home is indirectly ventilated with a powerful whole house...
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    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Nancy's Kailua Cottage Mauka1 / 15
    (8)Excellent
    1.4 kilometres from Lanikai Pillboxes
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2019
    This was the ideal spot for us, a pair of retired Canadians escaping a cold winter. Imagine walking just a few blocks to a gorgeous mile-long sandy beach, and just a few more...
    Reviewed 30 December 2018
    This was the perfect cottage for me, my wife and two young sons. She was on a maternity leave and I can work wherever there's Internet, so we relocated our family for six weeks...
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    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. Tourist License / Licencia de turismo N °: TATax ID #W40799764-01
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    Kailua, Oahu
    Holiday Rental House - 1 Bathroom, Sleeps 4
    42 feet from Kailua Beach. Exceptional Extended family Getaway1 / 73
    (6)Excellent
    2.0 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2019
    Had a wonderful time!Great location, beautiful beach, the house was well equipped for all beach related activities!
    Reviewed 10 June 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...
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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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    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Sheffield Suite Walk to Kailua Beach or Town1 / 13
    (1)Excellent
    1.9 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
    • Parking
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite...
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    Kailua, Oahu
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
    Beachfront Kailua, Oahu1 / 13
    (4)Excellent
    1.9 kilometres from Lanikai Pillboxes
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2018
    My husband and I took our adult children to this beautiful beach front home. On the beach yet set back enough to enjoy complete privacy. The house was perfect for our needs...
    Reviewed 9 April 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
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    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From...
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    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua All Taxes Included1 / 62
    (21)Excellent
    5.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2018
    We loved our stay with Patty and she made everything very comfortable and pleasant. We loved the view on the lanai and I would definitely stay there again. Lovely welcome...
    Reviewed 24 May 2018
    Loved staying at Patty & Bob's Kauhale apartment. There are lovely views of the mountains and wonderful breezes throughout the apartment which is very large and comfortable...
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    About this property
    Aloha! We are in compliance with Honolulu City and County Ordinance 18-19 (Bill 89), we welcome 30 day renters. The price is negotiable depending on number of occupants and length of stay. Please email owner for questions, current availability and pricing. Our ohana (family) welcomes you to...
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Oahu Apartment w/ Patio - Steps to Kailua Beach!1 / 24
    (1)Excellent
    2.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2018
    Exceptional hospitality; the owner is on site and very responsive. She greeted us and did everything to make our stay enjoyable. The appartment is well maintained and...
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    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    1.7 kilometres from Lanikai Pillboxes
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WElCOME TO PARADISE! Kailua is one of the most sought after vacation destinations in Oahu. Kailua is located on the Windward side of Oahu just 12 miles northeast of Honolulu - over Nu'uanu Pali, tallest mountain peak in the Ko'olau mountain range. Kailua offers picturesque, uncrowded beaches, great...
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    Kailua, Oahu
    Condo/Apartment - 1 Bathroom, Sleeps 2
    2.0 kilometres from Lanikai Pillboxes
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, 1000 sq ft island home in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. We offer a spacious master bedroom with a $3,000 California King bed, a second bedroom with a Queen size bed and...
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    Kailua, Oahu
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2.4 kilometres from Lanikai Pillboxes
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely hideaway two bedrooms are attached ' Ohana' to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.5 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Kailua, one block from a private beach access, our VW Vanagon camper has everything you need to have the most authentic Hawaii experience possible. Stationary unless an additional fee is paid (only for insurance purposes). Comes with access to a 2 man kayak, washer/dryer,...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright and very spacious 600 sq ft 1 bedroom in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. This cozy hide away has a cool prevailing ocean breeze and a quiet setting. In addition, this lanai...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.7 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    The best little Kailua beachtown getaway, this is a private apartment on a residential property. All the conveniences you need to make your vacation the best ever, at an affordable price. Privacy, Comfort and Convenience, with attention to details. Walking distance to shopping and restaurants, it...
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    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright and very spacious 500 sq ft studio in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. This cozy hide away has a cool prevailing ocean breeze and a quiet setting. In addition, this lanai is...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.8 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and inviting one bedroom apartment is on the upstairs of our beautiful Kailua home. With a separate gated entrance, the flat features an outdoor deck surrounded with palm trees and a view of the lush Koolau mountains. The interior is cool and inviting, with plenty of ventilation plus...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.5 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Walk to America's best beach. Run around Kailua.1 / 24
    (1)Very good
    1.4 kilometres from Lanikai Pillboxes
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned parking on property and laundry...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bathroom, Sleeps 3
    Your Private Place in Paradise - Sleeps 2 to 4!1 / 16
    (1)Very good
    2.6 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The majestically beautiful Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home. Tranquil, and safe, this home is in a quiet residential upscale...
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    Location Information
    Kailua, Oahu
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.6 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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 master to...
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    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.5 kilometres from Lanikai Pillboxes
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Boasting breathtaking panoramic ocean and Mokulua Islands views, gorgeous Lanikai Ocean View Villa awaits for your enjoyment and relaxation. Complete with a private pool and central air conditioning, this four-bedroom residence comfortably accommodates eight guests for the ultimate Hawaiian...
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    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.0 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Charming Cottage in beautiful Lanikai. Short walk to the beach. Enjoy comforts of home with efficiency kitchen and own washer and dryer. One split AC unit. Large lanai to extend the living space and room to BBQ and dine. Garden setting. Licensed B&B. This vacation home has been registered as a...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.5 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Experience the ultimate Hawaiian getaway at Kailani Villa, a modern two-story masterpiece nestled into a lush mountainside in Lanikai. Set back from the street and behind gates, it offers private island living. The villa’s spacious open floor plan, high ceilings, and travertine floors create a calm...
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    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.7 kilometres from Lanikai Pillboxes
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Nestled in the highly sought after wonderful Lanikai community, this beautiful executive home was newly built in 2014. This home is a perfect vantage point. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the spacious living area is...
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    Kailua, Oahu
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    1.0 kilometres from Lanikai Pillboxes
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming Lanikai Cottage features two dwellings on the same property, providing a total of three bedrooms and two bathrooms. Although separate, the dwellings share a private fenced-in yard with a new pool. Furnished in a beach-chic style, both offer the option of relaxing in air conditioning or...
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    Kailua, Oahu
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    4.1 kilometres from Lanikai Pillboxes
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it’s new...
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    Kailua, Oahu
    Condo/Apartment - 7 Bedrooms, 8 Bathrooms, Sleeps 14
    1.3 kilometres from Lanikai Pillboxes
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    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 and modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea, inhale the fragrant...
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    Kailua, Oahu
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    3.4 kilometres from Lanikai Pillboxes
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in central Kailua with private beach access steps from your front door, Hale Kalio will enchant you with its breathtaking views, central yet private location, and chic, Hawaii-modern decor. Experience the sounds of the waves and tradewinds from every room of this newly-remodeled...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    4.0 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    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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    Location Information
    Kailua, Oahu
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3.6 kilometres from Lanikai Pillboxes
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    Kailua’s famous white sand beach awaits! Hale Kimo offers guests a unique opportunity to enjoy a premier beach with private neighborhood access. Just follow the walking path from the home and you’ll find yourself on Kailua Beach, one of the most spectacular slices of shoreline on Oahu. With its...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.8 kilometres from Lanikai Pillboxes
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    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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    Location Information
    Kailua, Oahu
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
    1.3 kilometres from Lanikai Pillboxes
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 and modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea, inhale the fragrant...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.1 kilometres from Lanikai Pillboxes
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
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    Pet friendly
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    Smoking allowed
    About this property
    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze. Built in 2017, this brand new construction boasts upgraded appliances and furnishings meticulously hand picked by local designer, Lotus Home Staging. Throughout the home you will find many up-cycled wood...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    2.3 kilometres from Lanikai Pillboxes
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    Ke’aloha means “love,” and once you step inside this beachside Kailua cottage you’ll see why the name is so fitting. This four-bedroom, 2.5-bathroom home provides everything you need to enjoy island life. Separate guest quarters with a private entrance offer additional flexibility in accommodating...
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    Location Information
    Kailua, Oahu
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    4.3 kilometres from Lanikai Pillboxes
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement elegant indoor and lush outdoor spaces. Live each moment of your relaxing...
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    Kailua, Oahu
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.2 kilometres from Lanikai Pillboxes
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    2.1 kilometres from Lanikai Pillboxes
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Housekeeping Included
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    Pet friendly
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    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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    Location Information
    Kailua, Oahu
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.4 kilometres from Lanikai Pillboxes
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.2 kilometres from Lanikai Pillboxes
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how...
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    Location Information
    Kailua, Oahu
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    0.3 kilometres from Lanikai Pillboxes
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Mountain Views
    • Washer
    • Cable/satellite TV
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    • DVD Player
    • Grill
    • Balcony
    Suitability
    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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    Location Information
    Kailua, Oahu
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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