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Elder Access Vacation Rentals in Kailua, HI

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    Travellers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 23
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | 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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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 13
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    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... View all property information
    Location Information
    Kailua, Oahu
    1 / 28
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Mountain Views
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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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 14 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 to...
    5 of 5 stars Reviewed 11 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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    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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    Kailua, Oahu
    1 / 15
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with microwave, hot plate, toaster... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 6 August 2016
    We had a wonderful time at Simone's place. The apartment is very spacious and clean, the ocean really is just a couple of steps away. Simone and her kids are great hosts and were...
    5 of 5 stars Reviewed 3 August 2016
    We are in our 70's... but active... and found Simone and her family and the rental to be perfect for us. It's a 5 minute or less walk to the beach and within walking distance from...
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    1 / 13
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
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    • x
    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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars 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...
    5 of 5 stars Reviewed 23 March 2016
    While this property only rents for a month at a time, it was a great retreat from the world. With private beach access to a wide sandy beach and the wind in the palm trees, you...
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more... View all property information
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    Kailua, Oahu
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • DVD Player
    • Terrace
    • Balcony
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    • x
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    About this property
    Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five bedrooms, including one guest... View all property information
    Location Information
    Kailua, Oahu
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    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and... View all property information
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    Kailua, Oahu
    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
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Waterfront
    • Mountain Views
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    • x
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    • x
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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    Kailua, Oahu
    1 / 15
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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. View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 10 May 2016
    Nancy's Cottage was better than we expected, it was new, clean and had all the amenities we needed for our stay. It was also perfectly located, close to the beach and shops. There...
    5 of 5 stars Reviewed 12 August 2015
    Rick and Nancy's cottage is lovely on the inside, newly renovated, perfectly clean, well stocked, w an incredibly comfortable bed. I have back issues and this bed is as comfy as...
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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
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    • x
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    About this property
    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you... View all property information
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    Kailua, Oahu
    1 / 14
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Studio with private bath, private entrance and kitchenette, close to Kailua Beach & Park and Kailua town. The 240 sq foot Studio features a queen bed, pull out sofa bed, table and chairs, ceiling fan, TV, AC and High speed internet access. Pool on property. The kitchenette counter is equipped with... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 6 May 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a grill...
    5 of 5 stars Reviewed 16 February 2016
    We have stayed in the Garden Studio 3 times. We loved it so much we kept coming back. Excellent location, a five minute walk one direction takes you to beautiful Kailua Beach...
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    1 / 8
    4 of 5 stars (1) Very good
    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. <BR><BR>Complimentary assigned parking on property and laundry... View all property information
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    Kailua, Oahu
    1 / 10
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Private Garden
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    • DVD Player
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
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    • x
    About this property
    Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only 1-1/2 blocks to famous Kailua... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 6 January 2015
    Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • Ocean Views
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    • Balcony
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    • Pet-friendly
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    • x
    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... View all property information
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    Kailua, Oahu
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • Grill
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    • x
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    • x
    About this property
    The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5 minute drive to the beach. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy panoramic views of... View all property information
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    Kailua, Oahu
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    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Kailua, Oahu
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
    Location Information
    Kailua, Oahu
    1 / 24
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • DVD Player
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    • Satellite TV
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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
    5 of 5 stars Reviewed 4 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 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    Two Bedroom Premium Lockoff Villa An experience in rejuvenation, the 1,311-square-foot, two-bedroom, two-bath deluxe lockoff villa comfortably sleeps eight while providing every amenity necessary for your idyllic retreat in paradise. The two bedroom villa is your personal retreat with 1,311... View all property information
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    Kailua, Oahu
    1 / 22
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Coral Room seaside studio Tax ID 7873026-01 Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard with barbecue. Located in the best neighborhood in Kailua, enjoy the sounds of the ocean and feel the tropical trade winds.Has... View all property information
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    Kailua, Oahu
    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
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    • Mountain Views
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    • Pet-friendly
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    • x
    • x
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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
    4 of 5 stars Reviewed 10 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 19 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 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • x
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    • x
    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... View all property information
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    Kailua, Oahu
    1 / 11
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Our private rooms (3 total) are centrally located in Kailua with a short 5 minute walk to one of the worlds most beautiful beaches (Kailua Beach) and around a 10-15 minute walk into Kailua town where one can find a plethora of shopping options, restaurants, and local businesses. These rooms are... View all property information
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    Kailua, Oahu
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    This sweet Ohana apartment is quaintly situated downstairs with it's own private entrance. If you are looking to find a quiet location away from loud downtown Waikiki this Lanikai Ohana is perfect. It has a bedroom and bathroom with a full kitchen, full size refrigerator, living room and charming... View all property information
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    Kailua, Oahu
    1 / 7
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • Mountain Views
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    • x
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    • x
    About this property
    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 separate living quarters when you need privacy. This home is all on one level and... View all property information
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    Kailua, Oahu
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
    • Internet Access
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu