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Holiday Rentals with Pools in Kailua, HI

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    1 / 13
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 12
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C in the bedroom. There is a... View all property information
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    Kailua, Oahu 96734
    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    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... View all property information
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    Kailua, Oahu 96743
    1 / 13
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 27 February 2015
    I was visiting on my way back from TN and it was a very nice,quaint,quiet place and right outside a beautiful pool with lush landscaping... The couple that managed the place were...
    3 of 5 stars Reviewed 18 February 2015
    There are three separate rental residences on this property, and we rented all of them so that our family (daughter, her husband and two children, as well as our two adult sons...
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    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Kailua, Oahu
    1 / 37
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • x
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    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
    1 / 1
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This gated, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy, comfort, and social interaction. The seven bedrooms and seven... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 of 5 stars (23) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This gorgeous, beautifully furnished Ocean View home is a stone's throw from Kailua Beach and sleeps up to 8 comfortably. There is a large, sparkling, fully tiled swimming pool, 2 jacuzzi tubs, central air conditioning, 3 large bedrooms with ocean views, and 4 baths. Dolphin Manor is an... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 14 March 2016
    We loved the house. Big enough for everyone to have their own room and bathroom. Dining area to accommodate our family. The pool was our grandson's favorite part. We enjoyed the...
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    1 / 52
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    The Perfect BlendOhana Beach House is an elegant beach home ideally located just steps from world famous Lanikai Beach. It's light blue, sea foam green and white-washed wood décor give it a beachy island style, while warm colors, oversized rooms and fine linens give it a cozy and comfortable feel.... View all property information
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    Kailua, Oahu 96734
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***Longer minimum stay requirements may apply. Rates may vary depending on length of stay. Inquire for possible DISCOUNTS***Lanikai Beach CottageThe charming beach cottage has two separate dwellings on property that are rented together to provide 3 bedrooms and 2 baths. The main house is 2 bedroom,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed 11 January 2014
    Lots & lots of room. Family of 7 - 2 kids (8&10), 2 couples & single. So there was plenty of space that we could stay out of each others hair and off each others nerves. We...
    5 of 5 stars Reviewed 20 December 2013
    Our family of four, my friends family of 5 and my Mom and step father stayed here for 10days. I would recommend it. the beds were comfortable, as was the house. There was no air...
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    1 / 44
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    • x
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    About this property
    Royal Kailua Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green lawn,... View all property information
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    Kailua, Oahu 96734
    1 / 26
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Peaceful Energy of Maluhia Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The covered barbecue lanai area has... View all property information
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    Kailua, Oahu 96734
    1 / 24
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • 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
    5 of 5 stars Reviewed 5 July 2012
    Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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    1 / 15
    1 of 5 stars (1) Terrible
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Porch
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    • x
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    • x
    About this property
    A very nice updated 5 bedroom home that is located on a side street with no traffic. The beach entrance is a private street entrance 2 blocks away so you can walk to the beach but not have a large crowd of people on the beach. It is a very safe all white sand beach that is great for family's and... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 44
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    The Essence of Kailua Beach Living Castle Point Estateis 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... View all property information
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    Kailua, Oahu 96734
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is... View all property information
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    Kailua, Oahu 96734
    1 / 36
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Sauna
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    • x
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    About this property
    BALI RESORT TAT# W-89407732-02 Relax in the lap of luxury at this exquisite beachfront estate totaling nearly 60,000 sq ft. Spend lazy mornings strolling along the gorgeous stretch of the world-renowned Kailua Beach and sleepy afternoons relaxing beside the resort style pool with its bubbling... View all property information
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    Kailua, Oahu 96734
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    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... View all property information
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    Kailua, Oahu 96734
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    HONU HEAVEN TAT# W27612003-01 Just remodeled, beautiful vacation rental home at the beginning of Oahu's famous Lanikai Beach! 2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with privacy and manicured yard space, a... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 31
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    HALE HIKINA TAT# W17314247-01 Ensconce yourself in unpretentious luxury at Hale Hikina, where the indoors flow seamlessly into the outdoors with kingly travertine marble floors and exquisite custom furnishing. Enjoy soft sands, the warm embrace of the Pacific, cooling trade winds, and endless... View all property information
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    Kailua, Oahu 96734
    1 / 17
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    ROYAL BEACH ESTATE TAT# W54448892-01 Royal Beach Estate is one of the newest , most striking and contemporary executive beachfront estates on world renowned Kailua beach. Constructed in 2008, the estate features two homes (main house and guest house) separated by a resort-style pool with elegant... View all property information
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    Kailua, Oahu 96734
    1 / 16
    4.5 of 5 stars (24) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    Beautiful, licensed, newly remodeled 3 Bedrm, 3 Bath Kailua Beach side villa, surrounded with lush tropical gardens, on private estate with swimming pool and jacuzzi.. Just walk down a private beach lane and in less than 2 minutes you would be at the most beautiful beach in the country! It is a... View all property information
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    Kailua, Oahu 96734
    5 of 5 stars Reviewed 24 February 2015
    We stayed for one week and rented the three properties available for our extended family. Grandparents and two families of four with small children and babies. The rentals were...
    5 of 5 stars Reviewed 20 April 2014
    We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
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    1 / 32
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    The Paradise Point Estate is a rare jewel that comes fully appointed with Plantation style finishes and furnishings from around the world. Step from a secure entry and motor court into beachfront luxury that whispers old Hawaii, yet offers all of the latest amenities and technologies of a modern... View all property information
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    Kailua, Oahu 96734
    1 / 31
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR DETAILS. One-of-a-kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air... View all property information
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    Kailua, Oahu 96734
    1 / 10
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Located in Kailua and only minutes away from Kailua beach. Come and enjoy the nicest beaches on Oahu and one of the most beautiful stretches of sand in the world. This private unit is located off the main roads in residential Kailua, part of a family home. The suite is similar to a one-bedroom... View all property information
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    Kailua, Oahu 96734
    1 / 40
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Ohana Beach House is an elegant beach home ideally located just steps from world famous Lanikai Beach. It’s light blue, sea foam green and white-washed wood décor give it a beachy island style, while warm colors, oversized rooms and fine linens give it a cozy and comfortable feel. The home itself,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 19
    5 of 5 stars (5) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Located in the most prestigious area of Kailua, only a few houses away from where President Obama spends his Christmas vacation. This house is only one off the beach with Private Beach access. The house is 4 bedrooms with an additional room that can convert to a sleeping room. There are 4... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 5 April 2016
    We are a family of 10, including 4 young grandchildren, and we all loved our stay at "Kailua Beach Dream". This home is so spacious, clean and inviting! We found the beach to be...
    5 of 5 stars Reviewed 25 February 2016
    Our family of 10 has been traveling to warm climes together for the past 6 years and this house was our favorite so far! We were all able to comfortably relax together and...
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    1 / 39
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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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... View all property information
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    Kailua, Oahu 96734
    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Parking
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    • Pet-friendly
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    • x
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    About this property
    5 Minute Walk To Beach * Ocean View Beachside Home * Wrap-around Lanai * Spacious 2,200 SF 3BR, 2.5BA Home * Pool * Full Service Gourmet Kitchen * BBQ * Huge Master * Indoor Laundry * TV & WIFI * Parking * 2 Mile Walking Loop * Golf * Hiking Trail * Playground * Park * Also Available 600 SF 1BR -... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 9 May 2015
    enjoyed to time at the house. fun time with family to relax, sightseeing, beach adventures.... family enjoyed time here.
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    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Grill
    • Private Outdoor...
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A Hawaiian oasis awaits you, located on the island of Oahu, just a spectacular 20 minute drive from Honolulu and Waikiki. This Polynesian luxury home is an open and spacious beach house with exquisite tropical decor and high-end furnishings that flow gracefully out to the beautiful covered lanai... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 26 August 2014
    We loved the Kailua home. The home was well furnished and beautiful. The pool and location was amazing. Sheila (owner) was wonderful to work with and accommodating. If you are...
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    1 / 13
    8 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    8 bedroom, 18,000 square feet under roof, main and guest houses, private courtyard, cinema room, full cooking cabana poolside, laid-back luxury at its finest. View all property information
    Location Information
    Kailua, Oahu