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Kailua Holiday Rentals

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    Travellers to Kailua are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 313 Rentals in Kailua
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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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    Kailua, Cozy, Spacious Duplex Home1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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
    • 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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    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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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • 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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    Hale Ohana steps to Kailua Beach1 / 15
    (36)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Shared Garden
    • Parking
    • 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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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beachfront Plantation Cottage1 / 23
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • 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
    • 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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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely hideaway two bedrooms are attached ' Ohana' to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • 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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay** Escape the hustle and bustle of the city for a revitalizing retreat at this Kailua vacation rental studio with 1-bathroom and sleeping accommodations for 2. This exceptional rental...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Open Air Loft, Steps from beach1 / 16
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
    • Parking
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We spent 11 nights here and could have stayed much longer. With 2 beautiful beaches at the end of the road, fabulous snorkeling and incredible scenery all around, what more...
    Reviewed 4 weeks ago
    If relaxing in calm tropical Hawaiian atmosphere is what you want, look no further. Clean, spacious, nice view, full of cool breeze, kindest owner, and...a few minutes walk...
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    About this property
    Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with microwave, hot plate, toaster...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua Beach Cottage 2BD/2BA walk to the beach!1 / 23
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Secure Parking
    • DVD Player
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The cottage was comfortable, clean and equipped with all you need for a great island vacation! Very private. Christine & Frank are lovely hosts and the location is perfect...
    Reviewed 17 August 2017
    Christine and her family made us feel right at home during our four week stay at their beach cottage with our two kids ages 2 & 6. The cottage met all our needs. There were...
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    About this property
    Sandbar Cottage is an immaculate and beautifully appointed 2 bedroom / 2 bath unit located just a short stroll to one of the most beautiful beaches in the world, Kailua Beach. The unit is fully furnished with A/C in all rooms, cable TV, DVD player, Wi-Fi, washer/dryer, access to beach gear. It is...
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    Kailua, Oahu 96734
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Terrace
    • Ocean Views
    • Mountain Views
    • Washer
    • Balcony
    Suitability
    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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    Beachfront Hideaway1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    The house had everything we needed. The home is peaceful. A quick walk across the lawn and you're at the beach. How great is that! Early morning walks and coffee on the beach...
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    About this property
    Be prepared for absolute seclusion, with an electronic gate that opens and closes upon your arrival. Once inside the property, all you will hear are the birds, the sound of the surf pounding, and the rustle of the palm fronds from the many coconut trees on site. The house is right on the beach, and...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Wi-Fi
    • Housekeeping Included
    • Patio
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (14)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Satellite TV
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    The location was absolutely perfect! We were minutes away from Lanikai beach, hiking spots, food, and shopping. We were able to escape the people and the hustle and bustle by...
    Reviewed 22 February 2017
    I had a lovely week staying in Jacqui's tropical paradise studio with my husband, and two teen-aged sons. Jacqui went out of her way to make our stay welcoming and comfortable...
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    About this property
    Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bathroom, Sleeps 5
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua. The property is secluded with a...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • DVD Player
    • Ocean Views
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a young retired couple with our children all grown up and flown away! So we have decided to rent out the far wing of our home. We are 100 yards from the Ocean, a stroll down the driveway and 4 blocks from beautiful Kailua town where you will find tons of shops, restaurants and a great local...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (19)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 19 February 2017
    My son and I stayed here in the summer of 2015, and that is all my son has been talking about since.....we are going back this summer to stay in the Aloha Suite for a week and...
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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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description The Ohana Beachfront Villa is a 5-bedroom, 5.5 bathroom estate that offers a great view of Kailua Beach. You can enjoy the view from the ocean lanai and garden lanai, along with the landscaping. One of the best features of this home is a lagoon-style pavilion with tropical waterfalls...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
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    • 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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    Tropical Love Shack One Bedroom Steps to Kailua Beach1 / 16
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    • Satellite TV
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    I researched many hours on several applications before finding this rental as I am a seasoned traveler and naturally want to see everything. Nothing fit my expectations until I...
    Reviewed 5 June 2017
    What an amazing place to be... and when you're there, you feel as though you've been dropped into a very special part of heaven. The setting is truly tranquil, peaceful and...
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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. Our beautiful, 3 mile stretch of...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    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 and queen size beds, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes and flat boards....
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, 1000 sq ft island home in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. We offer a spacious master bedroom with a $3,000 California King bed, a second bedroom with a Queen size bed and...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    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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    Peaceful - Romantic - On #1 Rated Beach1 / 20
    (23)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Balcony
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    After two years of planning a long overdue family vacation, we decided that renting a house rather than staying at a hotel, was the best choice. After several searches online...
    Reviewed 11 February 2016
    ALOHA!!Our family has been staying Coral House Dec 27, 2015-Jan 2, 2016 Our family was a total of 11 people, including a nephew I rented the entire house.The most...
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    About this property
    Welcome to the one of the most beautiful spots in Hawaii! Far away reef protects us from big waves, white sands invite for long walks on the beach, warm ocean calls for all water activities. Prime location, just 2 minutes walk to the beach from the house, close to the airport and all Oahu...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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
    • 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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    Hale Maluhia Lanikai1 / 6
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 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
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. <BR>Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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
    • Satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Parking
    • 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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Your Private Place in Paradise - Sleeps 2 to 4!1 / 16
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Wi-Fi
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The majestically beautiful Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home.<BR><BR>Tranquil, and safe, this home is in a quiet residential...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Grill
    • 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the one of the most beautiful spots in Hawaii. Far away reef protects us from big waves, white sands invite for long walks on the beach and the ocean calls for all water activities. Prime location, just 2 minutes walk to the beach from the house, close to the airport and all Oahu...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 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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    • 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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    Kailua, Oahu 96734
    Private Room - 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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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Garden of dreams1 / 15
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Garden
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    • 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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    Charming 1 bedroom  house1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Washer
    • Grill
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • 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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    Dolphin Studio1 / 10
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    Everything you needed was there. The owners were lovely and a door knock away if you needed help. Everything that was in the pictures was there. The new air con was quite and...
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    About this property
    A comfortable and cozy place to stay with its own entrance and bath. Studio with private bath and separate entrance, AC, close to Kailua Beach Park and Kailua town, very reasonable accommodation. This Studio is furnished with a Queen bed, love seat, table and chairs, TV, AC and ceiling fan. You...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Sheffield Studio open 8/21-25 9/15-20, 9/27-10/10, 10/17-2010/23-30, 11/11-12/191 / 7
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • 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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful beachfront home set in a security gated neighborhood. Decorated with island style rattan furnishings, ceiling fans throughout, cool white tile and wooden floorings. Central A/C, gourmet kitchen with granite flooring and countertops. Enjoy the ocean view from the living room, dining...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 37
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the secluded breath taking beach from our fully furnished VERY LARGE 1 BEDROOM, a hideaway for groups from 1-3, our beautiful one bedroom one bath unit is separate and along side of a large 8 bedroom home with a separate entrance from the street, no shared common areas and complete privacy....
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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