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Holiday Rentals in Kailua, HI

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    Travellers to Kailua are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 12
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 30
    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 34
    5 of 5 bubbles (16) 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
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    • Pet-friendly
    • Child-friendly
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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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 1 week ago
    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 there...
    5 of 5 bubbles 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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    1 / 23
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Kailua, Oahu 96734
    1 / 16
    5 of 5 bubbles (4) 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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with microwave, hot plate, toaster... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 3 weeks ago
    The location was fantastic with a very short walk to the beautiful Kailua Beach Park. Our unit was roomy, light, well appointed and the bathroom was spacious. We enjoyed using...
    5 of 5 bubbles Reviewed 6 August 2016
    We had a wonderful time at Simone's place. The apartment is very spacious and clean, the ocean really is just a couple of steps away. Simone and her kids are great hosts and were...
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    1 / 13
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Outdoor Dining Area
    • Parking
    • Patio
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Shared Garden
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 23
    4.5 of 5 bubbles (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
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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 to...
    5 of 5 bubbles 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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    1 / 12
    4 of 5 bubbles (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...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles 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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    1 / 12
    4.5 of 5 bubbles (11) Very good
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Outdoor...
    • Internet Access
    • Waterfront
    • DVD Player
    • Patio
    • Satellite TV
    • Mountain Views
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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...
    4 of 5 bubbles Reviewed 3 February 2017
    Very pleasant place on a canal with swimming pool. Nice light. Dead-end Street with little traffic. Nice patio. Only issue was kitchen facilities, very small refrigerator, no sink...
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    1 / 15
    5 of 5 bubbles (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 10 May 2016
    Nancy's Cottage was better than we expected, it was new, clean and had all the amenities we needed for our stay. It was also perfectly located, close to the beach and shops. There...
    5 of 5 bubbles Reviewed 12 August 2015
    Rick and Nancy's cottage is lovely on the inside, newly renovated, perfectly clean, well stocked, w an incredibly comfortable bed. I have back issues and this bed is as comfy as...
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    1 / 7
    4.5 of 5 bubbles (2) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The Ginger Studio has free off... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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...
    4 of 5 bubbles Reviewed 31 January 2014
    We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool...
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C in the bedroom. There is a... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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 might...
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    1 / 24
    4.5 of 5 bubbles (2) Very good
    Private Room, 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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 2 weeks ago
    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...
    5 of 5 bubbles 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 night...
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 13
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 10
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Parking
    • Washer
    • Private Garden
    • Grill
    • DVD Player
    • Wi-Fi
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only 1-1/2 blocks to famous Kailua... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 7 January 2015
    Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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    1 / 21
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Patio
    • Parking
    • Wi-Fi
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    • Washer
    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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 be...
    5 of 5 bubbles 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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    1 / 28
    5 of 5 bubbles (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 14 March 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close to...
    5 of 5 bubbles Reviewed 11 March 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    1 / 19
    4.5 of 5 bubbles (25) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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...
    5 of 5 bubbles Reviewed 6 May 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a grill...
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • Grill
    • Patio
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5 minute drive to the beach. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy panoramic views of... View all property information
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    Kailua, Oahu 96734
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Grill
    • Patio
    • Hot Tub
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
    • Private Garden
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is... View all property information
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    Kailua, Oahu 96734
    1 / 15
    4.5 of 5 bubbles (36) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Shared Garden
    • Parking
    • Satellite TV
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    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach.<BR><BR>With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles 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 residential...
    5 of 5 bubbles 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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    1 / 33
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Parking
    • Mountain Views
    • Washer
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Experience true island living in this stunning historic beachfront residence on the white sandy shores of Lanikai. Hale Hinano is one of the original mansions built on the best part of Lanikai Beach in the 1940's, and has been beautifully renovated with extensive upgrades to become the luxurious... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Washer
    • Grill
    • Parking
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ** Please note that the owner of this home lives on the property, in an attached house with its own separate entrance. She's very friendly, but will be extremely respectful of your privacy. She will also serve as your own personal local contact, making it easy to assist you with any questions or... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 73
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
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    • Children's Pool
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    • Pet-friendly
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    • x
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    About this property
    Our home is located DIRECTLY on the Beach. Arguable the BEST BEACH, the BEST VIEWS, and on the BEST BEACH ACCESS in Hawaii. WONDERFULLY soft and manicured yard. LOTS of TEAK: lounge chairs, rocking chairs, porch swing, picnic tables, and accessories -THE HOUSE: Our home is tastefully decorated... View all property information
    Location Information
    Kailua, Oahu 96734 2324
    5 of 5 bubbles Reviewed 31 May 2015
    Our family got to spend a week in paradise in Dan's home. The view from the lanai is outstanding. Steps to the beach, all the beach and water toys one could ever hope for, perfect...
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    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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    • x
    About this property
    Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
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    Kailua, Oahu 96734
    1 / 7
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • x
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    • x
    About this property
    Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can be divided into three separate living quarters when you need privacy. This home is all on one level and... View all property information
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    Kailua, Oahu 96744
    1 / 41
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Private Garden
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This island style, open floor plan, family home is a five minute walk to Kailua beach. The huge lawn, play house, fire pit and saltwater pool (child safety fence upon request for a nominal set up charge) make this a fabulous home for families with kids. The adults will appreciate the gourmet, all... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 14 February 2017
    From the moment we pulled into the private gated driveway of this beautiful island home, we new we were in for a vacation we would never forget! The home is impeccably...
    5 of 5 bubbles Reviewed 10 February 2017
    We can't say enough good things about our recent stay at Holona Hale in Kailua! Our three sons are 9, 7 and 4, and if it was up to them we would have never left the property!! The...
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    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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... View all property information
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    Kailua, Oahu 96734
    1 / 15
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Porch
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    • x
    • ?
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    • x
    About this property
    A very nice updated 5 bedroom home that is located on a side street with no traffic. The beach entrance is a private street entrance 2 blocks away so you can walk to the beach but not have a large crowd of people on the beach. It is a very safe all white sand beach that is great for family's and... View all property information
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    Kailua, Oahu 96734
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
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    • x
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    • x
    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... View all property information
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    Kailua, Oahu 96734
    1 / 44
    7 Bedrooms, 8 Bathrooms, Sleeps 15 | Quick View
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    • x
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    About this property
    The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it's new... View all property information
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    Kailua, Oahu 96734
    1 / 30
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
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    About this property
    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR DETAILS. One-of-a-kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical... View all property information
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    Kailua, Oahu 96734
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This beautiful executive home in the wonderful Lanikai community was newly built in 2014. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the spacious living area is open and flows nicely for family gatherings. The kitchen with custom... View all property information
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    Kailua, Oahu 96734
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • x
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    About this property
    Kailani Villa Nestled on a lush mountainside in Lanikai, just one block from Lanikai Beach, you will find Kailani Villa: a two-story modern and luxurious masterpiece. Kailani Villa embodies modern elegance, punctuated by Hawaiian touches throughout.  Set behind gates and back from street level, it... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 37
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 30
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life will melt away. Most of the... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 19 August 2015
    Our stay was enhanced by the fact that the owners were available if and when there was any problem. I wondered what I would do if there were an emergency, car problems or medical...
    5 of 5 bubbles Reviewed 11 August 2015
    We have dreamed of going to Hawaii all of our lives and finally had the opportunity to go for our dream trip. I have to say that all of our expectations of Hawaii were filled...
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Private Outdoor...
    • Wi-Fi
    • Ocean Views
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement elegant indoor and lush outdoor spaces. Live each moment of your relaxing... View all property information
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    Kailua, Oahu 96734
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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    Kailua, Oahu 96734
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    Charming, Private, Hawaiian Style Home Kai Mele cottage has been featured in Coastal Living as guest house of the month, due to this private Kailua beachfront estate being nestled in among 40+ coconut trees and lush tropical gardens. With over 700 feet of an ancient lava rock wall surrounding this... View all property information
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    Kailua, Oahu 96734
    1 / 8
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. <BR><BR>Complimentary assigned parking on property and laundry... View all property information
    Location Information
    Kailua, Oahu 96734 6734
    1 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This executive beachfront home is right on Kailua Beach. Decorated with island-style rattan furnishings, ceiling fans throughout, cool white tile, and wood flooring. Central air conditioning, wonderful ocean views are just a few of the amenities. The gourmet kitchen comes with granite accents... View all property information
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    Kailua, Oahu 96734
    1 / 12
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Cozy "Ginger suite" studio in private home. Private entrance and bathroom. Three blocks from the beach. 1 block from the 57 bus stop. 3 blocks to shopping, restaurants and market. Air-conditioning and ceiling fan. Small covered patio. Little kitchenette for light meal prep. Small Refridg,... View all property information
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    Kailua, Oahu 96734
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Terrace
    • Balcony
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    • x
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    • x
    About this property
    Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five bedrooms, including one guest... View all property information
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    Kailua, Oahu 96734
    1 / 8
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 4 weeks ago
    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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    1 / 14
    3.5 of 5 bubbles (3) Average
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    About this property
    Lets be honest... one of the main reasons you're visiting Hawaii is for the beautiful weather year round and the jaw dropping beaches. Our vacation rentals are all within walking distance to one of the worlds most beautiful beaches, Kailua beach. Two of our properties (our Awakea & Ali'i... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 2 December 2016
    I stayed with a friend who has never been to Hawai'i! It was great showing her the part of the Island I grew up on. We walked to Kailua beach almost every morning. Everything we...
    4 of 5 bubbles Reviewed 26 February 2016
    Nice place to stay!!!!! I stayed with my 15 years old son for about 10 days.. This studio was very confortable and very well ubicated, we walk around Kailua from the studio and...
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    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!