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Kailua Holiday Rentals

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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
    4.5 of 5 bubbles (11) Very good
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 21
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    1 / 12
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Balcony
    • Secure Parking
    • Terrace
    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
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    • x
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    About this property
    Lovely Guest House with lots of upgrades<BR><BR>Large Bathroom with paintings of Lanikai Beach<BR><BR>California King Bed and 60inch Flat-Screen TV<BR><BR>Super Fast High-Speed Internet up to 60MB/s with WiFi Access<BR><BR>Full Kitchen with top of the line appliances <BR><BR>Washer and... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 1 week ago
    Peaceful and close walk to Kailua beach – great owners. This is a well-kept, charming place to visit on the east side of the island. If you're looking for a chill place away from...
    5 of 5 bubbles Reviewed 16 April 2016
    Private, near the beautiful beach but also close enough to town and shopping, restaurants, etc. The property shows pride of ownership and has most amenities you will need...
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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
    • x
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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 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 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 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    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
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    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 / 24
    4.5 of 5 bubbles (2) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • DVD Player
    • Air Conditioning
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    • 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 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...
    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 / 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 / 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 / 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 / 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
    Location Information
    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 March 2017
    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 / 8
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • x
    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles 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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    1 / 30
    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles 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...
    3 of 5 bubbles 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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    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
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    • 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
    Location Information
    Kailua, Oahu 96734
    1 / 10
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Private Garden
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    • DVD Player
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    • Outdoor Dining Area
    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 / 6
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
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    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles 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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    1 / 15
    5 of 5 bubbles (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Washer
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    • 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 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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 / 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 / 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
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    • Washer
    • Patio
    • Grill
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    • 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 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • DVD Player
    • Internet Access
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    • Satellite TV
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    • 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
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    Kailua, Oahu 96734
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
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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 3 | Quick View
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    • Ocean Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you... View all property information
    Location Information
    Kailua, Oahu 96821
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the... View all property information
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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
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    Kailua, Oahu 96734 6734
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Coral Room seaside studio Tax ID 7873026-01 Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard with barbecue. Located in the best neighborhood in Kailua, enjoy the sounds of the ocean and feel the tropical trade winds.Has... View all property information
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    Kailua, Oahu 96734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***Longer minimum stay requirements may apply.  Rates may vary depending on length of stay.  Inquire for possible DISCOUNTS*** Lanikai Beach Cottage The charming beach cottage has two separate dwellings on property that are rented together to provide 3 bedrooms and 2 baths. The main house is 2... View all property information
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    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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    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
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    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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    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
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 16
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... 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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    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 / 15
    4.5 of 5 bubbles (36) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Kailua, Oahu 96734
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    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    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
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Cozy Orchid studio in private home. Private entrance and bathroom. Three blocks from the beach. Air-conditioning and ceiling fan. Small covered patio with table & 2 chairs. Small light meal prep. area. Small Refrig, microwave, toaster, coffee maker, hotplate. Pots, utensils, dishes. Linens,... View all property information
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    Kailua, Oahu 96734
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    Luxury awaits! As Kailua's tallest oceanfront home, Whispering Palms offers unparalleled 280 degree views. Watch the sunrise or moon rise over the Mokulua Islands or the turtles and fish swimming outside your window. Beyond it's magnificent double art glass doors, you'll fine the Hawaiian home of... View all property information
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    Kailua, Oahu 96734
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    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 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    This home located can accommodate up to 12 people comfortably and can also be split in half to accommodate smaller parties. Located directly across the street from the Kailua Beach Park and Boat Launch, this modern rebuilt two-story home has a front main house consisting of 4 bedrooms, 4... View all property information
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    Kailua, Oahu 96734
    1 / 16
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a one bedroom rental unit... View all property information
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    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 20 October 2014
    This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
    5 of 5 bubbles Reviewed 10 March 2014
    I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Peaceful Energy of Maluhia Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The covered barbecue lanai area has... View all property information
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    Kailua, Oahu 96734
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    3.5 of 5 bubbles (3) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means “love,” is certainly appropriate for this cottage. From the moment you step inside this spectacular beach-side... View all property information
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    Kailua, Oahu 96734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can... View all property information
    Location Information
    Kailua, Oahu 96734
    Kailua holiday rentals

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

    What to do in Kailua

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

    Renting an apartment in Kailua

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