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Kailua Vacation Rentals

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    Travelers to Kailua are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    All 129 Rentals in Kailua
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    Open Air Loft, Steps from beach1 / 80
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Kailua Beach Cottage 2BD/2BA walk to the beach!1 / 23
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Holiday Palms - Private -5 min from Kailua beach1 / 24
    (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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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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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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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (16)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 2 weeks ago
    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...
    Reviewed November 25, 2017
    Our family of two adults and 10-year-old visited in mid-November and loved it! Truly a gem, if you want to escape the tourists and live like a local. Unit is as pictured and...
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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
    Rental Home - 1 Bathroom, Sleeps 5
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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
    • Cable/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. 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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    Lanikai Cottage1 / 26
    (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 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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    Beachfront Plantation Cottage1 / 46
    (3)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 January 6, 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...
    Reviewed November 27, 2015
    We had a marvelous time at this great location. The setting was perfect and the easy beach access and large lawn made for the best vacation in a long time.
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Cable/satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 1, 2017
    Great place, roomy, comfortable, enjoyed staying here...great location. Close to beach. Clean. Hosts are considerate and helpful. Wonderful atmosphere, perfect little getaway!
    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...
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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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refrigerator and freezer, You can...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Plantation Charm in Kailua1 / 30
    (5)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 1 week ago
    My family and I had a great time staying at Judy’s place. The location was perfect. It wasn’t too far of a drive to the places we needed to go, like Waikiki. Anywhere we went...
    Reviewed 2 weeks ago
    We booked this house for our family Christmas in Hawaii this year. We stayed 8 days: 3 adults and 1 elderly mom. The house is lovely. It's an older home that feels like classic...
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the most beautiful beach in Hawaii. Perfect location-just 1 min barefoot walk to warm sands. Modern , clean, safe and comfortable accommodations close to all Oahu attractions and just 17 min away from Honolulu airport. The 3 bedrooms , 3 bathrooms, the kitchen and the living room condo...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sheffield Studio open 10/22-27, 12/10-12/191 / 7
    (3)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    I returned to Sheffield Studio in Aug 2017 with my husband for an 11 night stay and it was very much as remembered from my previous visit in 2014. The location is great, you...
    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...
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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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    Kailua, Oahu 96734
    Private Room - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Kailua, Cozy, Spacious Duplex Home1 / 23
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 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 August 29, 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
    Rental Home - 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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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 and the 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Nancy's Kailua Cottage Makai1 / 28
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Cable/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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    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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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • Cable/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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    Kailua, Oahu 96734
    Condo/Apartment - 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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. 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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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Cable/satellite TV
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    • 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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    Nancy's Kailua Cottage Mauka1 / 15
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2017
    Nancy's Kailua Cottage is a wonderful place to stay. It was within walking distance to both the beach and Kailua town. The cottage is filled with all the amenities to make your...
    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...
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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. Tourist License / Licencia de turismo N °: TATax ID #W40799764-01
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
    • Parking
    • Patio
    • Cable/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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Spacious and quiet apartment at the back garden site of our home in Kailua, on the windward side of Oahu. Beautiful Kailua Bay invites you to relax or walk on the white sandy beach, enjoy the ocean (great for boogie boarding) year round balmy weather, and the special Hawaiian atmosphere. Hosts...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Garden of dreams1 / 15
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed July 27, 2017
    This place is wonderful! The owners are very welcoming and polite. It was a short distance to the beach and the owners actually have a pool and lounge area that we had full...
    Reviewed July 26, 2017
    Located in a quite area of Kailua, this place is a unique hidden gem. The studio is very comfortable, clean, well equipped with everything you may need for a perfect relaxing...
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    About this property
    Studio with private bath and entrance, air conditioning, internet access, kitchenette, use of pool. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toaster, vegetable steamer,...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Kailua Beachide- 2 houses from Kailua Beach!1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed June 17, 2017
    Thank you so much for the beach house! The beach was amazing - so close so beautiful ! Kailua is a treasure and such a wonderful escape from the leeward crowds. We so much...
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    About this property
    The lovely Kailua Beachside House is a 2 bedroom 2 bath house that is great for families and couples alike. It's location can't be beat only 2 houses from the world famous white sands of Kailua Beach. This house is perfect for those wanting fun in the sun! On your short stroll back from the beach...
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    Kailua, Oahu 96734
    Private Room - 2 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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    Pet friendly
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    Smoking allowed
    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. Tranquil, and safe, this home is in a quiet residential upscale...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Kalaka Beachside Welcome to Paradise in beautiful Kailua, Hawaii! This beautifully appointed 5-bedroom, 3 bathroom Hawaiiana home is the perfect retreat for family and friends. Just one house off the beach, Kalaka Beachside has a lovely park and ocean view from the kitchen, great room and pool. A...
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    Kailua, Oahu 96734 2301
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 52
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
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    • Mountain Views
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Serenity Beachfront Cottage1 / 8
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Palione Papalani Two Bedroom Steps to Kailua Beach1 / 16
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Washer
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 20, 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...
    Reviewed March 10, 2014
    I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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    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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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming 1 bedroom  house1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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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
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
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    • Porch
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    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. Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings is...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 37
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Grill
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    • Hot Tub
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    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come bask in the gentle trades of the windward side at the Kailua Palms Estate Guest House, a fabulous two bedroom, two bath vacation guest house located in sleepy Kailua Town near Kailua Beach. The two bedrooms are spacious and comfortable. You will like the relaxed and casual indoor/outdoor...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    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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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Hawaiian style home is a perfect peaceful getaway for you and your extended family. It's just steps from one of the most beautiful tourist-free beaches on the island of Oahu. Listen to the waves crashing as you relax on the lanai, or barbeque for your group in true outdoor Hawaiian fashion....
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
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    Pet friendly
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    Smoking allowed
    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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    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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 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 March 23, 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 6 bedroom, 5 bath beachfront home reminiscent of Old Hawaii. Coconut trees abound throughout the spacious lush green lawns which leads directily on to the white sandy beach of Kailua. The home sits on one of the most breath taking beaches in the world. Walk the beach in the...
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    Location Information
    Kailua, Oahu 96734 2726
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Kailua Flight and Weather Info
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    Honolulu Intl Airport
    13.4 miles from Kailua
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    Additional Kailua Info

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    • Local time: 12:06 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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