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Holiday Rentals and Homes in Kailua, HI

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    Travellers to Kailua are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 24
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 12
    5 of 5 bubbles (8) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 15
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
    Location Information
    Kailua, Oahu 96734
    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...
    5 of 5 bubbles Reviewed 3 August 2016
    We are in our 70's... but active... and found Simone and her family and the rental to be perfect for us. It's a 5 minute or less walk to the beach and within walking distance from...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach... View all property information
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    Kailua, Oahu 96734
    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 / 13
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 34
    5 of 5 bubbles (12) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Porch
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    • 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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 7 July 2016
    We had a wonderful stay at Suite Aloha. The suite is impeccably clean with cute and tasteful island decor. It is also stocked with everything you would want for a stay at the...
    5 of 5 bubbles Reviewed 14 February 2016
    My husband and I stayed here for 6 days while in Oahu and we were very pleased with the accommodations. The owners were very friendly and we were treated like friends instead of...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Balcony
    • Secure Parking
    • Terrace
    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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 16 April 2016
    Private, near the beautiful beach but also close enough to town and shopping, restaurants, etc. The property shows pride of ownership and has most amenities you will need...
    5 of 5 bubbles Reviewed 3 October 2015
    Wonderful immaculate, quiet, spotlessly clean, idyllic guest bungalow with charming porch and grassy front yard. Walk to Kailua Beach, Kiteboarding, Restaurants, Bike Rental, and...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Mountain Views
    • Ocean Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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 2 weeks ago
    ''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 / 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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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 / 7
    4 of 5 bubbles (1) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
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    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
    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 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 30
    4 of 5 bubbles (2) 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
    • ?
    • 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 4 weeks ago
    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 / 21
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Patio
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    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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 / 17
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • DVD Player
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    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 15
    5 of 5 bubbles (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
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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 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... 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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    • Pet-friendly
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    • x
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    • 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 / 12
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 10
    5 of 5 bubbles (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • 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 / 13
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 9 April 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
    5 of 5 bubbles Reviewed 23 March 2016
    While this property only rents for a month at a time, it was a great retreat from the world. With private beach access to a wide sandy beach and the wind in the palm trees, you...
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    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Satellite TV
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    • 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 / 15
    4.5 of 5 bubbles (35) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • 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
    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...
    4 of 5 bubbles Reviewed 29 May 2016
    The place is in a very good location, you can walk to cafes and restaurants, or the beach. The studio apartment is very nice, with a good bed. We slept very well. But here is one...
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    1 / 8
    4 of 5 bubbles (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. <BR><BR>Complimentary assigned parking on property and laundry... View all property information
    Location Information
    Kailua, Oahu 96734 6734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can... View all property information
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    Kailua, Oahu 96734
    1 / 8
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Cozy Orchid studio in private home. Private entrance and bathroom. Three blocks from the beach. Air-conditioning and ceiling fan. Small covered patio with table & 2 chairs. 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
    1 / 22
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
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    • x
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    • Smoking allowed
    • x
    About this property
    Completely Renovated Cottage in Kailua in very close walking distance to the beach.<BR>High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub.<BR>Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed.<BR>Our... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 12 April 2016
    This is an excellent rental if you're looking for a place away from the resorts and tourists. Great location with a 5 minute walk to the best beach on Oahu. Plenty of...
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    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Mountain Views
    • Grill
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    • Waterfront
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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 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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
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    Kailua, Oahu 96821
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 6
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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 / 14
    4.5 of 5 bubbles (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    Studio with private bath, private entrance and kitchenette, close to Kailua Beach & Park and Kailua town. The 240 sq foot Studio features a queen bed, pull out sofa bed, table and chairs, ceiling fan, TV, AC and High speed internet access. Pool on property. The kitchenette counter is equipped with... View all property information
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    Kailua, Oahu 96734
    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...
    5 of 5 bubbles Reviewed 16 February 2016
    We have stayed in the Garden Studio 3 times. We loved it so much we kept coming back. Excellent location, a five minute walk one direction takes you to beautiful Kailua Beach...
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    1 / 22
    4.5 of 5 bubbles (19) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
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    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 13 July 2016
    If you're looking for 5 star accomodation, this is not the place for you, however if you want a place to stay that's comfortable in a convenient location, then this will suit you...
    5 of 5 bubbles Reviewed 14 May 2016
    This house was everything we saw online. The managers went out of their way to provide us with a VitaMix to make our morning smoothies. We thought there would be bicycles...
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    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    This exquisitely furnished apartment is located in one of Kailua's most coveted neighborhoods on a ridge overlooking Kailua Beach. Watch the surfers on Flat Island as you enjoy breakfast on your beautiful lanai. Between the views, the exquisite furnishings and the generous closets with built-ins,... 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 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,... View all property information
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    Kailua, Oahu 96734
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Outdoor Dining Area
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    • x
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    About this property
    Stay like locals! Hotel in Waikiki doesn't excite you? Quiet and beautiful Kailua is the best option for you and your family! We offer a beautiful Hawaiian-theme guesthouse with spacious, 15 ft high-ceiling 2 bedroom, 1 bath with full kitchen where 4-5 people can sleep. One of the rooms have a... View all property information
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    Kailua, Oahu 96734
    1 / 7
    9 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    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 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Enjoy the island lifestyle at beautiful Mokulua Cottage, situated on beachfront property-just steps from the sand! This incredibly spacious two bedroom/one bathroom home is perfectly suited for your island getaway. A full renovation was recently completed in February 2016 with many upgrades... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Over the canal, past the boat ramp and round the bend is where you’ll find the Ocean’s Edge in Lanikai. Just a walk on the beach, afternoon swim or bike ride away! This 5 bedroom, 3.5 bath oceanfront home is set dramatically close to and slightly above the ocean’s edge. The living room’s picture... View all property information
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    Kailua, Oahu 96734
    1 / 10
    5 of 5 bubbles (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
    Location Information
    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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    1 / 33
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
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    Kailua, Oahu 96734
    1 / 7
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Garden
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    • x
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    About this property
    Guests are sure to enjoy a memorable vacation in this wonderful fully furnished, 3 bedroom/2 bath plantation bungalow in one of the most desired neighborhoods on Oahu; Kaimalino is a small, upscale, very quiet and safe community, situated on the northern end of Kailua town. The house was designed... View all property information
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    Kailua, Oahu 96734
    1 / 14
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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
    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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    1 / 37
    8 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Grand Kailua Beachside Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green... View all property information
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    Kailua, Oahu 96734
    1 / 6
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    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 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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
    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!