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Holiday Rentals and Homes in Kailua, HI

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    Travellers to Kailua are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    5 of 5 stars (11) Excellent
    1 Bedroom, 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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    1 / 21
    5 of 5 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    1 / 28
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
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    • Patio
    • Grill
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    • Pet-friendly
    • Wheelchair access
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    • Elder access
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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 96734
    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 / 12
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Balcony
    • Secure Parking
    • Terrace
    • Mountain Views
    • Private Garden
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    • Child-friendly
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    About this property
    Lovely Guest House with lots of upgrades Large Bathroom with paintings of Lanikai Beach California King Bed and 60inch Flat-Screen TV Super Fast High-Speed Internet up to 60MB/s with WiFi Access Full Kitchen with top of the line appliances Washer and Dryer Amazing patio with outdoor... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 16 April 2016
    Private, near the beautiful beach but also close enough to town and shopping, restaurants, etc. The property shows pride of ownership and has most amenities you will need...
    5 of 5 stars Reviewed 3 October 2015
    Wonderful immaculate, quiet, spotlessly clean, idyllic guest bungalow with charming porch and grassy front yard. Walk to Kailua Beach, Kiteboarding, Restaurants, Bike Rental, and...
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    1 / 24
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Secure Parking
    • Balcony
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI is the PERFECT Blend of Town and Beach Living................... Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the world famous... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 25 October 2015
    Best location - walk to beach, walk to town (many, many restaurants to choose from). Apartment is very clean, modern, and comfortable, pictures are true to experience. Location is...
    5 of 5 stars Reviewed 12 April 2015
    I know people do not want to overstate their claims about their rental property. These accommodations were over the top!. We had friends who lived in the same side of the...
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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Shared Garden
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Washer
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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    Kailua, Oahu 96734
    1 / 21
    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Balcony
    • Private Outdoor...
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,... View all property information
    Location Information
    Kailua, Oahu 96734
    3 of 5 stars Reviewed 6 days ago
    Try to arrive during daylight as the lane/driveway to access the rental is a bit tricky. We arrived very late but once we located it we had east access via key in locked...
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    1 / 22
    4.5 of 5 stars (18) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Washer
    • Secure Parking
    • Wi-Fi
    • Grill
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 1 week ago
    This house was everything we saw online. The managers went out of their way to provide us with a VitaMix to make our morning smoothies. We thought there would be bicycles...
    5 of 5 stars Reviewed 10 August 2015
    We loved staying in this house. My family of 3, my mother, and my sister and one of her kids stayed in this house. It was perfect for cooking meals, and hanging out. The front...
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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • Wi-Fi
    • Outdoor Dining Area
    • Patio
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    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 96734
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    1 / 7
    4 of 5 stars (1) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed 31 January 2014
    We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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    1 / 13
    5 of 5 stars (1) Excellent
    Private Room, 3 Bathrooms, Sleeps 3 | Quick View
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    • Balcony
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    BOOK DIRECTLY THROUGH OWNER AND SAVE 5%! Step back in time and soak up a peaceful, private, quintessential Hawaiian vacation experience. (if this suite is booked, please ask me about our other suites!) Please note we do charge $15 extra per night for a third person. The PINEAPPLE SUITE is a NEWLY... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 14
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Secure Parking
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Lets be honest... one of the main reasons you're visiting Hawaii is for the beautiful weather year round and the jaw dropping beaches. Our vacation rentals are all within walking distance to one of the worlds most beautiful beaches, Kailua beach. Two of our properties (our Awakea & Ali'i... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed 26 February 2016
    Nice place to stay!!!!! I stayed with my 15 years old son for about 10 days.. This studio was very confortable and very well ubicated, we walk around Kailua from the studio and...
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
    • Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Kailua, Oahu 96821
    1 / 10
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Parking
    • Washer
    • Private Garden
    • Grill
    • DVD Player
    • Wi-Fi
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • 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 96734
    5 of 5 stars Reviewed 7 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 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
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 11
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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 a... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 3 weeks ago
    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 / 15
    5 of 5 stars (4) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 96734
    5 of 5 stars Reviewed 2 weeks ago
    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 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
    • Wi-Fi
    • Washer
    • Mountain Views
    • Secure Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Completely Renovated Cottage in Kailua in very close walking distance to the beach. High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub. Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed. Our Cottage... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 12 April 2016
    This is an excellent rental if you're looking for a place away from the resorts and tourists. Great location with a 5 minute walk to the best beach on Oahu. Plenty of...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
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    • Outdoor Dining Area
    • Patio
    • Private Garden
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cute Bungalow! 2 1/2 blocks from beautiful Kailua Beach. Cool AC. King size bed. Kitchenette for cooking with all you need to make meals and eat at home to save $ . Nestled in a private lane and just a 10 min walk to the beach. This is a stand alone unit, so you have the place to yourself. Our... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 15
    4.5 of 5 stars (32) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Shared Garden
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach. With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed 18 November 2015
    This is a very cute and comfortable room and it was very reasonable for Ohau. My husband and I had stayed right on the ocean and paid a lot more on Kuai, but we were looking for...
    5 of 5 stars Reviewed 28 July 2015
    We were blown away for how great this place was given the pricetag. A beautiful comfortable room in a really great part of Oahu. The host was lovely to deal with. Short walking...
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    1 / 10
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Grill
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 stars Reviewed 20 October 2014
    This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
    5 of 5 stars Reviewed 10 March 2014
    I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
    • Satellite TV
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
    Location Information
    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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    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Washer
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    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 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 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    • Housekeeping...
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Kailua, Oahu 96734
    1 / 26
    5 of 5 stars (23) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    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 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • DVD Player
    • Waterfront
    • Grill
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This relaxing beach house is a well-maintained, nicely furnished four bedroom, three bath contemporary home with den and approx. 2,200 sq. ft. located in a security-gated neighborhood near the center of Kailua Beach. High ceilings and sliding glass doors in the main living areas provide a feeling... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    • Washer
    • Ocean Views
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    • Pet-friendly
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    • x
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    About this property
    Kailua Ohana is a 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... View all property information
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    Kailua, Oahu 96734
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    About this property
    The Pineapple Ohana is situated in a quiet neighborhood where the local experience of the 50th state comes alive daily. Kailua Town and beach are a 3 block walk. Newly remodeled and furnished, this fun house is filled with all the necessary kitchen and bath amenities along with an outdoor grill and... View all property information
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    Kailua, Oahu
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Mountain Views
    • Outdoor Dining Area
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    About this property
    Stay like locals! Hotel in Waikiki doesn't excite you? Quiet and beautiful Kailua is the best option for you and your family! We offer a beautiful Hawaiian-theme guesthouse with spacious, 15 ft high-ceiling 2 bedroom, 1 bath with full kitchen where 4-5 people can sleep. One of the rooms have a... View all property information
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    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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    • Internet Access
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    • 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 96734
    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 / 9
    5 of 5 stars (2) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Garden
    • Wi-Fi
    • Private Garden
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    • Mountain Views
    • Porch
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Airy and bright bedroom with private bathroom in house with resident owner in Kailua. Backyard faces a canal that empties into ocean. Dock and barge boat for afternoon relaxation. Hiking, windsurfing and ocean sports, lovely beaches, and shopping within 2 miles. Waikiki and airport easy to... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 21 April 2016
    Georgia provided a clean bedroom and bathroom, free access to the common kitchen and living areas, and delightful conversation. We rented her spare vehicle, which was reliable...
    5 of 5 stars Reviewed 29 July 2015
    Georgia T is an excellent host whose hospitality made my stay in Kailua really memorable. As well as the large, en suite room I stayed in, I had access to kitchen, lounge and...
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    1 / 20
    6 Bedrooms, 5 Bathrooms, Sleeps 19 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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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
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    Kailua, Oahu
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Parking
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    • Pet-friendly
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    • Child-friendly
    • x
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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
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Child-friendly
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    About this property
    Cozy 'Ginger suite' studio in private home. Private entrance and bathroom. Three blocks from the beach. 1 block from the 57 bus stop. 3 blocks to shopping, restaurants and market. Air-conditioning and ceiling fan. Small covered patio. Little kitchenette for light meal prep. Small Refridg,... View all property information
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    Kailua, Oahu 96734
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Internet Access
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    • Waterfront
    • Satellite TV
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    • Mountain Views
    • Parking
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    • Pet-friendly
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    • x
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    About this property
    Enjoy the island lifestyle at Mokulua Cottage! This spacious two bedroom, one bath house is perfectly suited for your island getaway. A full renovation was just completed in February 2016, making this home feel brand new! Master bedroom is complete with King sized bed and walk in closet, our guest... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Hot Tub
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    • ?
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    About this property
    Over the canal, past the boat ramp and round the bend is where you'll find the Ocean's Edge in Lanikai. Just a walk on the beach, afternoon swim or bike ride away! This 5 bedroom, 3.5 bath oceanfront home is set dramatically close to and slightly above the ocean's edge. The living room's picture... View all property information
    Location Information
    Kailua, Oahu 96734
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
    • Outdoor Dining Area
    • Mountain Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
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    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach... View all property information
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    Kailua, Oahu 96734
    1 / 25
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Welcome to the old Oahu world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870s, he become the contractor of choice for Queen Liliuokalani. Walker erected such notable buildings as the Bishop Museum and Honolulu Hale, or City Hall. John Walker’s inviting and... 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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    • Internet Access
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    • Pet-friendly
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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 / 15
    1 of 5 stars (1) Terrible
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Private Outdoor...
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    • Porch
    • DVD Player
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    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
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    Kailua, Oahu 96734
    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. Complimentary assigned parking on property and laundry... View all property information
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    Kailua, Oahu 96734 6734
    1 / 13
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
    • Satellite TV
    • Patio
    • Grill
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
    • 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 96734
    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 / 24
    8 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Terrace
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Balcony
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    About this property
    Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu’s northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination. The grounds are covered in lush tropical flora with panoramic views of... View all property information
    Location Information
    Kailua, Oahu 96734
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Patio
    • Waterfront
    • Ocean Views
    • Mountain Views
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Ocean Front House, 2 Bdrm/2 Bath + Ohana Room, Sleeps 4-6. Great outdoor spaces. Honu Hale Lanikai (Honu means turtle, Hale means house) is a simple and comfortable two bedroom oceanfront vacation home in beautiful Lanikai on the island of Oahu. It has one bedroom/one bath in the main house and a... View all property information
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    Kailua, Oahu 96734
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
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    • Pet-friendly
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    About this property
    This executive beachfront home is right on Kailua Beach. Decorated with island-style rattan furnishings, ceiling fans throughout, cool white tile, and wood flooring. Central air conditioning, wonderful ocean views are just a few of the amenities. The gourmet kitchen comes with granite accents... View all property information
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    Kailua, Oahu 96734
    1 / 36
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • x
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    About this property
    KAILUA SURF TAT# W99825381-01 BEACHFRONT luxury on world renowned Kailua Beach. Ocean and beach views are the focus of this contemporary home with expansive living and dining areas. Has an ultra-modern kitchen with German appliances. Travertine Flooring and wood finishes. Large Master Bedroom... View all property information
    Location Information
    Kailua, Oahu 96734
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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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 / 42
    5 of 5 stars (13) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Patio
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    • DVD Player
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    • Hot Tub
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • x
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    About this property
    Hawaii GET and TAT ID# OII968I4-OI Our ohana (family) welcomes you to 'Kauhale' our beautiful Hawaiian home. We offer a large cool and breezy 1000 sq ft, 1 bedroom, 1 bath, private, 2nd floor apartment, includes all utilities, located in a great family neighborhood, vaulted open beam ceilings... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 11 February 2016
    My niece, her husband and twins age 17 months visited Hawaii for the first time, stayed in this amazing unit. They were impressed with the expanse of the unit, the beautiful...
    5 of 5 stars Reviewed 12 January 2016
    My husband, 26 year old daughter and I spent 6 nights at Patty and Bob's apartment and loved it. The apartment is spacious and although only one BR, the second bed is in an...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cozy Orchid studio in private home. Private entrance and bathroom. Three blocks from the beach. Air-conditioning and ceiling fan. Small covered patio with table & 2 chairs. Little kitchenette for light meal prep. Small Refridg, microwave, toaster, coffee maker, hotplate. Pots, utensils, dishes.... View all property information
    Location Information
    Kailua, Oahu 96734
    Kailua holiday rentals

    Kailua is a town on the Windward Coast of Oahu in Hawaii. The coast in general is renowned as an area of outstanding natural beauty, and Kailua is a great place to see some spectacular sunrises. With some great beaches and a laidback lifestyle, Kailua is the ideal destination for a relaxed family holiday. And with a huge amount of self-catered accommodation available in the town, you can find a home from home in this idyllic island setting. A trip to Hawaii might not sound like a money saving holiday, but there are rental homes available to suit every budget, and free up cash to enjoy the rest of your family holiday.

    What to do in Kailua

    Kailua Beach Park will be the first stop for many tourists, and this amazing ocean beach is bound to take up a few days of your visit. Work on your tan, and admire the sea turtles which can be seen in the area. Also, watersports enthusiasts will love the opportunities provided by Kailua Beach, including kayaking, windsurfing, kiteboarding and scuba diving. All necessary equipment can be hired nearby for some unforgettable holiday experiences. Quite apart from exploring the rest of the Windward Coast and Oahu in general, you will also have to take a boat out to the Mokulua Islands, two small islands just off Oahu's coast which provide great surfing opportunities and slightly less crowded white sandy beaches.

    Renting an apartment in Kailua

    With a huge variety of family friendly rental homes available in and around Kailua, it is easy to find deals on luxurious apartment rentals. With rental costs starting from just £390 for apartments large enough to accommodate a family of four or more, it can work out much less expensive than booking hotel rooms for the entire family. Many of the apartments come with spectacular ocean views, as well as access to private pools, tennis courts and other facilities, so it will certainly not feel like a low cost option! The extra privacy and space that comes with a rented holiday property also means that they're great for kids - the youngest members of your family can run around and let off steam without you having to worry about them disturbing the neighbours!