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Kailua Holiday Rentals

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    Travellers to Kailua are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 130 Rentals in Kailua
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    Open Air Loft, Steps from beach1 / 16
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (15)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    Kailua Beach Cottage 2BD/2BA walk to the beach!1 / 46
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Cable/satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Great place, roomy, comfortable, enjoyed staying here...great location. Close to beach. Clean. Hosts are considerate and helpful. Wonderful atmosphere, perfect little getaway!
    Reviewed 18 March 2017
    Attractive clean, quiet studio with well-equipped kitchen and bath. Within walking distance of Kailua beach, Kalapawai Market, and Buzz's Lanikai. My wife and I have stayed...
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    About this property
    Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find comfort...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Kailua, Cozy, Spacious Duplex Home1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We enjoyed our recent stay at the duplex home. The living area is very spacious with a fully stocked kitchen. Owner has done an exceptional job with the lighting and ventilation...
    Reviewed 29 August 2017
    Great place with very helpful hosts. Can't wait to go back! Near a number of excellent beaches and places to see.
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    About this property
    This 850 sq ft duplex consists of a very spacious living room with a vaulted ceiling, 1 bedroom, 1 full bath and a full kitchen with oven. All the areas come with ceiling fans and the home is indirectly ventilated with a whole house fan. The bedroom has a queen bed and comfortably sleeps two...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2017
    Beautiful ocean front rental in a quiet neighborhood. Nice pool area. Very relaxing. We enjoyed our 6 night stay very much!
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    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...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Plantation Charm in Kailua1 / 30
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2016
    The house was beautiful and the pool was an added delight. It was a great place for 7 adults. My only complaint was that the mattress in the master bedroom was so bad I had to...
    Reviewed 21 May 2016
    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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    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,...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Beachfront Plantation Cottage1 / 46
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2017
    We arrived and were delighted to discover this special spot ..... Paradise. Exactly how it is depicted in photos - quaint, roomy, well equipped and so beautiful being so close...
    Reviewed 27 November 2015
    We had a marvelous time at this great location. The setting was perfect and the easy beach access and large lawn made for the best vacation in a long time.
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    About this property
    Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Nancy's Kailua Cottage Makai1 / 28
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    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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    About this property
    Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Holiday Palms - Private -5 min from Kailua beach1 / 24
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    This accommodation was very clean and well stocked for day trips whether they be for picnics or a day at the beach! Wonderful
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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...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the most beautiful beach in Hawaii. Perfect location-just 1 min barefoot walk to warm sands. Modern , clean, safe and comfortable accommodations close to all Oahu attractions and just 17 min away from Honolulu airport. The 3 bedrooms , 3 bathrooms, the kitchen and the living room condo...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Nancy's Kailua Cottage Mauka1 / 15
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    Nancy's Kailua Cottage is a wonderful place to stay. It was within walking distance to both the beach and Kailua town. The cottage is filled with all the amenities to make your...
    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...
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    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. Tourist License / Licencia de turismo N °: TATax ID #W40799764-01
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bathroom, Sleeps 4
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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2015
    I enjoyed our stay in Lanikai, the cottage was perfect. The fully stocked kitchen made making tea to cooking a breeze. It was so easy to get to the beach and easy to find hikes...
    Reviewed 9 April 2015
    Lanikai cottage is less than 1 block from Lanikai beach, with a fantastically equipped kitchen- toaster, blender, mixer etc . There are ceiling fans in every room. Views are of...
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    About this property
    This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kaimalino Retreat1 / 13
    (1)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2017
    A very nice place to relax. The studio is big and has everything you expect from a condo. The private garden invites to eat outside or hang on the outdoor sofa. The night is...
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    About this property
    Kaimalino translates to 'calm waters' in Hawaiian and is a very quiet, restful place...as is this unit. Relax indoors or outdoors under a large pergola, in a private enclosed courtyard looking out at the many fruit and flower trees on the property. The studio has a full kitchen, and the covered...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Hale Ohana steps to Kailua Beach1 / 15
    (36)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Garden
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 January 2017
    This was like a new hotel room in a private home. We had a separate side entrance. We were within walking distance from the beach, restaurants, and shopping, in a nice...
    Reviewed 3 September 2016
    If you choose Hawaii, you have to choose Tina's studio. No wonder celebrities have their vacation at Kailua. The apartment is perfect and the lush garden makes both inside and...
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    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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming 1 bedroom  house1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua by the Sea Studio1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2017
    Pros: close to a very nice, non busy beach. Very private for being on atop of a homeowners garage. Very Clean and updated. Good location to town and other amenities. Close to...
    Reviewed 11 September 2016
    We have been to Oahu before and it is rare to find such a modern/ updated place to stay. It was clean and so convenient. We had enough toiletries, bath towels etc. for our 3...
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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...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lanikai Ocean View Retreat1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 November 2016
    ''High up in the hill'' overlooking the nice Lanekai beach, giving a fresh breeze and the nice sound of the waves on the reefs. It is recommended to have a car. The driveway...
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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...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sheffield Studio open 10/22-27, 12/10-12/191 / 7
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2017
    This studio really fulfilled all the expectations that me and my wife have when we are out travelling and searching for good accomodation. Rachel and her husband are very...
    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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    About this property
    Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The Ginger Studio has free off...
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    Kailua, Oahu 96734
    Private Room - 1 Bathroom, Sleeps 2
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    Garden Studio1 / 15
    (25)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Patio
    • Outdoor Dining Area
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2017
    I had a wonderful time staying in this little studio! It's clean and quiet, and I had nightly gecko visitors (which I loved)! The owners are on site, and seemed like very nice...
    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...
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    About this property
    Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or outdoor dining on the lanai....
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua, Cozy, 2 bedroom, Duplex Home1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 850 sq ft duplex consists of a master bedroom with a queen bed and a huge walk-in closet. Access to the full bathroom is through the master bedroom. The other bedroom also has a queen bed. All the areas come with ceiling fans and the home is indirectly ventilated with a powerful whole house...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Garden of dreams1 / 15
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2017
    This place is wonderful! The owners are very welcoming and polite. It was a short distance to the beach and the owners actually have a pool and lounge area that we had full...
    Reviewed 27 July 2017
    Located in a quite area of Kailua, this place is a unique hidden gem. The studio is very comfortable, clean, well equipped with everything you may need for a perfect relaxing...
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    About this property
    Studio with private bath and entrance, air conditioning, internet access, kitchenette, use of pool. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toaster, vegetable steamer,...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Serenity Beachfront Cottage1 / 8
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    This is a modest 2-bedroom, 1-bathroom cottage in a wonderful location. You take exactly 85 steps across the private lawn shown in the PR photo and are on one of the most...
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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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    From the time we made our reservation to our arrival and our stay, it couldn't have been more smooth and enjoyable.The cottage and property was beautiful and was a piece of...
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    About this property
    This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio is detached from the...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Spacious and quiet apartment at the back garden site of our home in Kailua, on the windward side of Oahu. Beautiful Kailua Bay invites you to relax or walk on the white sandy beach, enjoy the ocean (great for boogie boarding) year round balmy weather, and the special Hawaiian atmosphere. Hosts...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Private Lanikai house w/tropical gardens & hot tub1 / 30
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    Plumeria, avocado, and mango trees surrounded by red and pink ginger; red, pink, white, and yellow hibiscus; orchid; heliconia; anthurium, and many more tropical plants enclosed by rocks walls, fencing, and an 8 foot hedge to create a private tropical paradise. The sounds of the small waterfall...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
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    • Porch
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    Pet friendly
    Kid friendly
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    Reviewed 11 March 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would...
    Reviewed 21 July 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
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    About this property
    Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings is...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Create life long memories and experience Hawaiian local living in the comfortable and beautiful 'Kaimana in Kailua'. Kaimana (Diamond) in Kailua is a 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in Kailua! The house resides on the...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Walk to America's best beach. Run around Kailua.1 / 8
    (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...
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    Kailua, Oahu 96734 6734
    Holiday Rental House - 1 Bathroom, Sleeps 3
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home located can accommodate up to 12 people comfortably and can also be split in half to accommodate smaller parties. Located directly across the street from the Kailua Beach Park and Boat Launch, this modern rebuilt two-story home has a front main house consisting of 4 bedrooms, 4...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cozy Cottage 5 Minute Walk to Kailua Beach1 / 26
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 4 weeks ago
    If you are looking for a five star Motel on Waikiki, this is the wrong place. But, if you are looking for a great place to rest and sleep after days filled with adventure and...
    Reviewed 12 October 2017
    We stayed at Kay's vacation rental for 5 nights and we have a great experience. The family who runs the place were very attentive and quick to response to any of our questions...
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    About this property
    Our 1 bedroom/1 bath Cottage is located on our Ali'i property which is centrally located in Kailua with a short 5 minute walk to one of the top rated beaches in the world Kailua Beach, and a 10-15 minute walk into Kailua town. Our cozy cottage is equipped with king size beds, spacious living room...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!1 / 28
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Housekeeping Included
    • Patio
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2017
    First let me start by saying the hospitality from Mike and Kelly were above and beyond what I expected. The process was super simple from check in to check out. All texts and...
    Reviewed 24 August 2017
    We loved our stay here! The home was clean and well laid out offering space for our group of 7 adults. Kitchen was clean and well appointed. The beach was just an easy walk away...
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    About this property
    This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor plan offers a serene Hawaiian...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    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...
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    Location Information
    Kailua, Oahu 96821
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
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    • Shared Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period... Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and full size...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach1 / 44
    (21)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2016
    If you're looking for 5 star accomodation, this is not the place for you, however if you want a place to stay that's comfortable in a convenient location, then this will suit...
    Reviewed 14 May 2016
    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...
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    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....
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Terrace
    • Ocean Views
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one house off of the beach in central Kailua with private beach access 10 steps from your front door, Hale Ina Kalio will enchant you with it's breathtaking views, central yet private location and chic, Hawaii-modern decor. This house just completed a total renovation and is a brand new...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    The quaint Kailua-Kalama 'Cottage'1 / 10
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bathroom, Sleeps 2
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    Palione Papalani Two Bedroom Steps to Kailua Beach1 / 16
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Washer
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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 one bedroom rental unit...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your White Sand Beach Awaits... Hale Kimo is located just a beach path away from one of the most beautiful beaches in all of Oahu, Kailua beach! The beach has very limited public access, making for an exclusive beach experience on Oahu! This two story custom home is your perfect Hawaiian Hale with...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beachfront Kailua, Oahu1 / 13
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kailua Beachide- 2 houses from Kailua Beach!1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Patio
    • Internet Access
    • Washer
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2017
    Thank you so much for the beach house! The beach was amazing - so close so beautiful ! Kailua is a treasure and such a wonderful escape from the leeward crowds. We so much...
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    About this property
    The lovely Kailua Beachside House is a 2 bedroom 2 bath house that is great for families and couples alike. It's location can't be beat only 2 houses from the world famous white sands of Kailua Beach. This house is perfect for those wanting fun in the sun! On your short stroll back from the beach...
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    Kailua, Oahu 96734
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Cute garden cottage - walking distance to Kailua Beach and Beach Park - private entrance & bath - kitchenette - sleeps 2 adults In your private beach cottage you'll sleep soundly on a firm queen-size bed. A three-step ladder accesses the sleeping loft. Safety bar for the bed is available but does...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Relaxing Private Room- 5 Min Walk to Kailua Beach1 / 7
    (3)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    Great place to spend time in Kailua. Beach is close, shops and poke even closer...Looking forward to return. Thanks!
    Reviewed 11 March 2017
    Room was a 2 minute drive to the beach and ~5-10 minute walk. Room has all you need and clean but definitely is on the smaller side. Air conditioning worked perfectly. The...
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    About this property
    Our private room is the perfect accommodation for parties of 2 who are looking to relax and enjoy Kailua without breaking the bank. Enjoy our centrally located property in Kailua with a short 5 minute walk to one of the worlds most beautiful beaches (Kailua Beach) and a 10-15 minute walk into...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Washer
    • Cable/satellite TV
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    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description 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. It's just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the most beautiful spots in Hawaii. Perfect location- just 1 min barefoot walk to warm sands and close to Oahu attractions. Comfortable, large studio with king size bed and double futon, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes, flat boards....
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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!

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