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Kailua Vacation Rentals

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    Travelers to Kailua are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 306 Rentals in Kailua
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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (13)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    Beachfront Plantation Cottage1 / 23
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Open Air Loft, Steps from beach1 / 16
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • Satellite TV
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2015
    I enjoyed our stay in Lanikai, the cottage was perfect. The fully stocked kitchen made making tea to cooking a breeze. It was so easy to get to the beach and easy to find hikes...
    Reviewed April 9, 2015
    Lanikai cottage is less than 1 block from Lanikai beach, with a fantastically equipped kitchen- toaster, blender, mixer etc . There are ceiling fans in every room. Views are of...
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    About this property
    This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 34
    (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
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 18, 2017
    Attractive clean, quiet studio with well-equipped kitchen and bath. Within walking distance of Kailua beach, Kalapawai Market, and Buzz's Lanikai. My wife and I have stayed...
    Reviewed February 19, 2017
    My son and I stayed here in the summer of 2015, and that is all my son has been talking about since.....we are going back this summer to stay in the Aloha Suite for a week and...
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    About this property
    Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find comfort...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hale Ohana steps to Kailua Beach1 / 15
    (36)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Shared Yard
    • Parking
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 21, 2017
    This was like a new hotel room in a private home. We had a separate side entrance. We were within walking distance from the beach, restaurants, and shopping, in a nice...
    Reviewed September 3, 2016
    If you choose Hawaii, you have to choose Tina's studio. No wonder celebrities have their vacation at Kailua. The apartment is perfect and the lush garden makes both inside and...
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    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach.<BR><BR>With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,...
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    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Nancy's Kailua Cottage Makai1 / 28
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close...
    Reviewed March 11, 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    About this property
    Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would...
    Reviewed July 21, 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
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    About this property
    Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. <BR>Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Serenity Beachfront Cottage1 / 8
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 24, 2017
    This is a modest 2-bedroom, 1-bathroom cottage in a wonderful location. You take exactly 85 steps across the private lawn shown in the PR photo and are on one of the most...
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    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    'E komo mai  "Welcome"1 / 30
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    The house was beautiful and the pool was an added delight. It was a great place for 7 adults. My only complaint was that the mattress in the master bedroom was so bad I had to...
    Reviewed May 21, 2016
    Try to arrive during daylight as the lane/driveway to access the rental is a bit tricky. We arrived very late but once we located it we had east access via key in locked...
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    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Sheffield Studio open 5/3-8, 5/17-26, 4/23, 6/3-13, 6/21-291 / 7
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2017
    This studio really fulfilled all the expectations that me and my wife have when we are out travelling and searching for good accomodation. Rachel and her husband are very...
    Reviewed January 30, 2014
    We were surprised just how spacious this studio is and how nice and fresh it is.Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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    About this property
    Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The Ginger Studio has free off...
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you...
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    Location Information
    Kailua, Oahu 96821
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Lanikai Ocean View Retreat1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 18, 2016
    ''High up in the hill'' overlooking the nice Lanekai beach, giving a fresh breeze and the nice sound of the waves on the reefs. It is recommended to have a car. The driveway...
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    About this property
    My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C in the bedroom. There is a...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Holiday Palms - Private -5 min from Kailua beach1 / 12
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
    • Air Conditioning
    • Washer
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2017
    This accommodation was very clean and well stocked for day trips whether they be for picnics or a day at the beach! Wonderful
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    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely hideaway two bedrooms are attached " Ohana" to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Walk to America's best beach. Run around Kailua.1 / 8
    (1)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. <BR><BR>Complimentary assigned parking on property and laundry...
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    Location Information
    Kailua, Oahu 96734 6734
    Rental Home - 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Hale Maluhia Lanikai1 / 6
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
    • Parking
    • Patio
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Shared Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Satellite TV
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Last minute special rate!  Studio with AC, off street parking, Pool & WiFi1 / 19
    (25)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Patio
    • Outdoor Dining Area
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 5, 2017
    I had a wonderful time staying in this little studio! It's clean and quiet, and I had nightly gecko visitors (which I loved)! The owners are on site, and seemed like very nice...
    Reviewed May 6, 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a...
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    About this property
    Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or outdoor dining on the lanai....
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua by the Sea Studio1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2017
    Pros: close to a very nice, non busy beach. Very private for being on atop of a homeowners garage. Very Clean and updated. Good location to town and other amenities. Close to...
    Reviewed September 11, 2016
    We have been to Oahu before and it is rare to find such a modern/ updated place to stay. It was clean and so convenient. We had enough toiletries, bath towels etc. for our 3...
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    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach...
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming 1 bedroom  house1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Private Yard
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    BEST BEACH---BEST VIEWS---BEST LOCATION--BEST HOME1 / 73
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    • Mountain Views
    • Children's Pool
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 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...
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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...
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    Location Information
    Kailua, Oahu 96734 2324
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute garden cottage - walking distance to Kailua Beach and Beach Park - private entrance & bath - kitchenette - sleeps 2 adults In your private beach cottage you'll sleep soundly on a firm queen-size bed. A three-step ladder accesses the sleeping loft. Safety bar for the bed is available but does...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The quaint Kailua-Kalama "Cottage"1 / 10
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed January 6, 2015
    Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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    About this property
    Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only 1-1/2 blocks to famous Kailua...
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    Kailua, Oahu 96734
    Rental Home - 1 Bathroom, Sleeps 2
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    Nancy's Kailua Cottage Mauka1 / 15
    (5)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
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    Reviewed May 10, 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...
    Reviewed August 12, 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...
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    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun.
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    Kailua, Oahu 96734
    Rental Home - 1 Bathroom, Sleeps 4
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 13
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed April 27, 2017
    From the time we made our reservation to our arrival and our stay, it couldn't have been more smooth and enjoyable.The cottage and property was beautiful and was a piece of...
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    About this property
    This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio is detached from the...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Large Spacious Studio - 5 Min Walk to Kailua Beach1 / 14
    (3)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed December 2, 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...
    Reviewed February 26, 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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    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...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tropical Love Shack One Bedroom Steps to Kailua Beach1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    Reviewed 3 weeks ago
    What an amazing place to be... and when you're there, you feel as though you've been dropped into a very special part of heaven. The setting is truly tranquil, peaceful and...
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    About this property
    Blossoms, palms and tiki’s welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua’s beautiful beach, 75 yards via private right of way. Our beautiful, 3 mile stretch of...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As you step into the Maile Suite the first thing you will notice is how fresh, airy and up to date it is. The full sized bed with crisp white linens begs you to take a late afternoon nap after spending the day playing in the surf. The spacious and clean private bathroom is updated with...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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,...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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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,...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Create life long memories and experience Hawaiian local living in the comfortable and beautiful "Kaimana in Kailua". Kaimana (Diamond) in Kailua is a 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in Kailua! The house resides on the...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Your Private Place in Paradise - Sleeps 2 to 4!1 / 16
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    The majestically beautiful Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home.<BR><BR>Tranquil, and safe, this home is in a quiet residential...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Peaceful - Romantic - On #1 Rated Beach1 / 20
    (22)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Balcony
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    Pet friendly
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    Smoking allowed
    Reviewed February 11, 2016
    ALOHA!!Our family has been staying Coral House Dec 27, 2015-Jan 2, 2016 Our family was a total of 11 people, including a nephew I rented the entire house.The most...
    Reviewed December 10, 2015
    Lanikai Estate is an excellent property and is just as nice in person as it is in the photo description.
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    About this property
    Welcome to the one of the most beautiful spots in Hawaii! Far away reef protects us from big waves, white sands invite for long walks on the beach, warm ocean calls for all water activities. Prime location, just 2 minutes walk to the beach from the house, close to the airport and all Oahu...
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    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua. The property is secluded with a...
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    Kailua, Oahu 96734
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As you step into the Plumeria Suite the first thing you will notice is how fresh, airy and up to date it is. The queen sized bed with crisp white linens begs you to take a late afternoon nap after spending the day playing in the surf. The spacious and clean private bathroom is updated with...
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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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...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
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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...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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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...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom/1 Bath Units-5 min walk to Kailua Beach1 / 21
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 2017
    What a wonderful stay we had. A great holiday let comfortable, cozy, clean and stylish. And they thought of everything you could need from a toaster to a body board. Plus it is...
    Reviewed January 26, 2016
    Convenient Condo in walking distance to the beautiful Kailua Beach, where parking might be a problem. It provides fair space in the living room and bedroom. WiFi and a modern TV...
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    About this property
    We have a 1 bedroom/1 bath Cottage and a 1 bedroom/1 bath Apartment both located on our Alii property. Our Alii property is centrally located in Kailua with a short 5 minute walk to Kailua Beach which is one of the top rated beaches in the world, and around a 10 - 15 minute walk into Kailua town....
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how...
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    Kailua, Oahu 96743
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    About this property
    This 850 sq ft duplex consists of a master bedroom with a queen bed and a huge walk-in closet. Access to the full bathroom is through the master bedroom. The other bedroom also has a queen bed. All the areas come with ceiling fans and the home is indirectly ventilated with a powerful whole house...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    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,...
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    Kailua, Oahu 96734
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Private Outdoor Pool (Heated)
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    • Ocean Views
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Kailua Flight and Weather Info
    Airports nearby (1)
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    HNL
    Honolulu Intl Airport
    13.3 miles from Kailua
    Low airfares recently found by TripAdvisor travelers
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    75° 68°
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    76° 69°
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    78° 70°
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    Additional Kailua Info

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    • Local time: 02:51 AM (HST)
    • Peak travel: March - April
    Kailua Vacation Rentals

    Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

    A Kailua Vacation

    Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

    Family-Friendly Kailua

    From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.

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