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Kailua House Rentals

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    Travellers to Kailua are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    69 Matching Rentals in KailuaView all 127 rentals
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    Affordable Place on the Best Beach in Hawaii1 / 18
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (22)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Hale Ohana steps to Kailua Beach1 / 15
    (37)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua, Cozy, Spacious Duplex Home1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    We enjoyed our recent stay at the duplex home. The living area is very spacious with a fully stocked kitchen. Owner has done an exceptional job with the lighting and ventilation...
    Reviewed 30 August 2017
    Great place with very helpful hosts. Can't wait to go back! Near a number of excellent beaches and places to see.
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    About this property
    This 850 sq ft duplex consists of a very spacious living room with a vaulted ceiling, 1 bedroom, 1 full bath and a full kitchen with oven. All the areas come with ceiling fans and the home is indirectly ventilated with a whole house fan. The bedroom has a queen bed and comfortably sleeps two...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming 1 bedroom  house1 / 12
    (2)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 Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2018
    My grand daughter an I had the best time ever!!! Thomas was very nice and the house was perfect, the beach was beautiful . Our stay in Oahu could not have been better!!!
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    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tropical Kailua Studio on the Water w/Private Pool1 / 36
    (17)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2018
    Remember that time you went to stay with family at their lake house in Hawaii… Just like that, only better! Friendly hosts, and perfect location to base your Oahu adventures.
    Reviewed 28 December 2017
    Wonderful, quiet neighbourhood a short drive or cycle into Kailua town centre. Large well-equipped lanai with lots of seating, stacks of beach toys to use and a gas barbecue...
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    About this property
    Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bathroom, Sleeps 5
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    ON BEAUTIFUL KAILUA BEACH1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 February 2018
    Ania, the owner, was friendly and helpful. The location is ideal - just around the corner from a beach with few people and trees for shade. Plenty of restaurants nearby. We had...
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    About this property
    Welcome to the most beautiful spots in Hawaii. Perfect location- just 1 min barefoot walk to warm sands and close to Oahu attractions. Comfortable, large studio with king size bed and double futon, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes, flat boards....
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beachfront Plantation Cottage1 / 23
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2018
    Our family of four ( two teens 13.5 and 16 yrs) stayed at the plantation cottage and loved that it was right on Kailua/kalama beach. The house is older and has some wear and...
    Reviewed 7 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...
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    About this property
    Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely hideaway two bedrooms are attached ' Ohana' to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2015
    I enjoyed our stay in Lanikai, the cottage was perfect. The fully stocked kitchen made making tea to cooking a breeze. It was so easy to get to the beach and easy to find hikes...
    Reviewed 10 April 2015
    Lanikai cottage is less than 1 block from Lanikai beach, with a fantastically equipped kitchen- toaster, blender, mixer etc . There are ceiling fans in every room. Views are of...
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    About this property
    This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hale Maluhia Lanikai1 / 6
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2017
    Beautiful ocean front rental in a quiet neighborhood. Nice pool area. Very relaxing. We enjoyed our 6 night stay very much!
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    About this property
    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Kailua, Cozy, 2 bedroom, Duplex Home1 / 29
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    We enjoyed our stay at this place. J &R were great with suggestions and making us feel at home. The location was great, near 2 of the best beaches in Hawaii. When I was told...
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period... Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and full size...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5-minute drive to the beach. It's just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Mountain Views
    • Grill
    • Parking
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tranquil Tropical Beach Retreat1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Terrace
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    We had the most amazing vacation solely due to our hosts, Amber and Matt, in their beautiful guest house. We absolutely had everything available to us that we could think of...
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    About this property
    Come enjoy this two story private Hawaiian style guesthouse in a tranquil setting of tropical flowers and fruit trees. Sip a cup of coffee or glass of wine while you enjoy the view of the Ko'olau mountains and listen to the birds sing from your covered upstairs lanai. Take a dip and catch some...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 25 February 2017
    This is a modest 2-bedroom, 1-bathroom cottage in a wonderful location. You take exactly 85 steps across the private lawn shown in the PR photo and are on one of the most...
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    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Mountain Views
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!1 / 70
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Perfect place to stay, just a short walk to a great beach. We stayed there with 8 people and had plenty of room for all of us. Gracious and attentive hosts.
    Reviewed 29 September 2017
    First let me start by saying the hospitality from Mike and Kelly were above and beyond what I expected. The process was super simple from check in to check out. All texts and...
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    About this property
    This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor plan offers a serene Hawaiian...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy Cottage 5 Minute Walk to Kailua Beach1 / 13
    (17)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Garden
    • Grill
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The cottage is a one bedroom located within walking distance to beach and shopping area that has a variety of restaurants, local stores and chains (Whole Foods and Longs...
    Reviewed 16 January 2018
    Cute and spacious cottage! No problems checking in or out. Stores, restaurants and beach is near by. Restaurants close by were vegan and vegetarian friendly. The kitchenette...
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    About this property
    Our 1 bedroom/1 bath Cottage is located on our Ali'i property which is centrally located in Kailua with a short 5 minute walk to one of the top rated beaches in the world Kailua Beach, and a 10-15 minute walk into Kailua town. Our cozy cottage is equipped with king size beds, spacious living room...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Palione Papalani Two Bedroom Steps to Kailua Beach1 / 16
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2018
    This a very well maintained, clean, and attractive apartment on the second floor of a private residence with private entrance. The rooms are ample and as the owners describe...
    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...
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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 one bedroom rental unit...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Parking
    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Wi-Fi
    • Terrace
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and cheerful Tropical Garden Studio closer to award winning Kailua Beach and Lanikai. The Studio is close to public transport, the city center, Kailua Beach, art and culture. You’ll love my place because of the location and the people. My place is good for couples, solo adventurers,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Shangri La By The Sea - Stunning views with pool - ID1 / 42
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description 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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note the homeowner lives on site, in a completely separate unit, and may be present during your stay* Your next Hawaiian getaway eagerly awaits at this 3-bedroom, 1-bath vacation rental house, just a 5 minute-drive from Kailua Beach. This home sleeps 5 guests and offers Koolau Mountain...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful beachfront home set in a security gated neighborhood. Decorated with island style rattan furnishings, ceiling fans throughout, cool white tile and wooden floorings. Central A/C, gourmet kitchen with granite flooring and countertops. Enjoy the ocean view from the living room, dining...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beachfront Kailua, Oahu1 / 13
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
    Reviewed 24 March 2016
    While this property only rents for a month at a time, it was a great retreat from the world. With private beach access to a wide sandy beach and the wind in the palm trees, you...
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    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Hawaiiana home just steps from the world famous Kailua Beach. This Hawaiiana beach house is the perfect place to relax and enjoy paradise. The tropical large living room opens onto a spacious private lawn leading out directly via a gate to a sandy walkway, steps to breathtaking Kailua beach. A...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
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    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Envy of All Paradises In the middle of the great Pacific, on the world's most isolated chain of island, lies a small coastal community that is blessed with heaven-like beauty. LANIKAI, the “heavenly sea”. The envy of all paradises.   It's crystal clear waters, white sand beaches and lapping...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach1 / 22
    (21)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 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...
    Reviewed 15 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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    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....
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Parking
    • Waterfront
    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it's new...
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    Kailua, Oahu 96734
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    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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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Description The Ohana Beachfront Villa is a 5-bedroom, 5.5 bathroom estate that offers a great view of Kailua Beach. You can enjoy the view from the ocean lanai and garden lanai, along with the landscaping. One of the best features of this home is a lagoon-style pavilion with tropical waterfalls...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Create life long memories and experience Hawaiian local living in the comfortable and beautiful 'Kaimana in Kailua'. Kaimana (Diamond) in Kailua is a 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in Kailua! The house resides on the...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • Mountain Views
    • Patio
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Brand New Pool is the gathering spot of this majestic island home. 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...
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    Kailua, Oahu 96734
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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    BEACHFRONT 6BR/4.5BA Kailua family style with Pool1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Patio
    • Grill
    • Waterfront
    • Outdoor Dining Area
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2013
    Wonderful location right on the beach and perfect home to celebrate my birthday with all 16 members of my family. Decor was a little dated but adequate. Loved being on the...
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    About this property
    Kailua Beach House is a casual, two-story 6 bedroom, 4.5 bath beachfront home with 5,000 square feet of living space. The 1/2 acre privacy-fenced property features a large, free-form swimming pool which has a poolside cabana with a shower and a built-in BBQ. The property decor features light...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    Fabulous Luxury 5 Bedroom Kailua Beachfront-Private Pool and Spa1 / 24
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Me and my husband ( grandma and grandpa) and our three adult children, their spouses and their five children just came home from a glorious time in this elegant yet comfortable...
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    About this property
    Three-quarter acre gated estate on Kailua Beach with pool, spa, beach vollyball and unobstructed sunrise ocean views from horizon to horizon. This Luxury Kailua Villa is a fabulous corner of paradise located on world famous Kailua Beach. This property is very secluded, located at the end of a white...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Large Spacious Studio - 5 Min Walk to Kailua Beach1 / 7
    (4)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Mountain Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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...
    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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    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. Our properties Ali'i property is a short 5 minute...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This spacious room has a private bathroom and its own entrance. Located just 5-10 walking minutes from Kailua Beach and Beach Park. Enjoy the shade of the Plumeria trees. This room is furnished with a queen size bed, small refrigerator, television and coffee maker. High speed internet access is...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
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    • Ocean Views
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your White Sand Beach Awaits... Hale Kimo is located just a beach path away from one of the most beautiful beaches in all of Oahu, Kailua beach! The beach has very limited public access, making for an exclusive beach experience on Oahu! This two story custom home is your perfect Hawaiian Hale...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    About this property
    Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu’s northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination. The grounds are covered in lush tropical flora with panoramic views of...
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    Kailua, Oahu 96734
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Charming Cottage in beautiful Lanikai. Short walk to the beach. Enjoy comforts of home with efficiency kitchen and own washer and dryer. One split AC unit. Large lanai to extend the living space and room to BBQ and dine. Garden setting. Licensed B&B. This vacation home has been registered as a...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    42 feet from Beautiful Kailua Beach  Wonderful 4 Bedroom Home  Lots of Extra's1 / 73
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Internet Access
    • Waterfront
    • DVD Player
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    • Mountain Views
    • Children's Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 June 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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