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Holiday Rentals in Kailua

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    Travellers to Kailua are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    All 75 Rentals in Kailua
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    Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $2201 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Plantation Charm in Kailua1 / 30
    (5)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Nancy's Kailua Cottage Makai1 / 32
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Sheffield Studio  Walk to Kailua Beach or Town1 / 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 Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2017
    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 1 February 2017
    This studio really fulfilled all the expectations that me and my wife have when we are out travelling and searching for good accomodation. Rachel and her husband are very...
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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
    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (30)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 6 June 2019
    This is an awesome location with the beach an easy couple of block walk. It is also an easy walk to the city center for restaurants, stores, and more. And you can't ask for...
    Reviewed 4 April 2019
    When you stay in Suite Aloha in Kailua you are guaranteed to have an extremely friendly welcome from Sabine and Ray and to enjoy your stay enormously. The accommodation is...
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    About this property
    Come and Play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find comfort...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Lanikai Cottage1 / 13
    (3)Very good
    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 16 September 2019
    The cottage is beautifully updated and is fully stocked with everything you need.It is very spacious, and I love the white decor!The beach chairs are a bit old; the straps...
    Reviewed 9 July 2015
    I enjoyed our stay in Lanikai, the cottage was perfect. The fully stocked kitchen made making tea to cooking a breeze. It was so easy to get to the beach and easy to find hikes...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Kailua Beach Aloha Cottage1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2018
    First up Ryan said he wanted us to have a 5 star experience in his messaging to me. We booked this for first 3 nights of 2018. Kailua is a great area. You did get was stated but...
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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this Charming Cottage in beautiful Lanikai. Enjoy the convenience of relaxing on a beautiful Short walk to the beach nightly, and get lost in the comforts of a cozy home with an efficiency kitchen and your own washer and dryer in the home. There is One split AC unit. Property has a Large...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Parking
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Kalaheo Beach House is a spacious 2 bedroom, 1 1/2 bath traditional plantation home offering an authentic Hawaiian living experience in a private, serene, garden setting, only steps away from world famous Kailua Beach. Welcome to our charming remodeled vintage Hawaiian style 2 bedroom, 1 1/2...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TAT-*******-7072-01 This property is a legally established dwelling that is rented for period of 30 consecutive days or more at any one time regardless of actual occupancy. Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take advantage of our vacation rental in Kailua Oahu, and enjoy a family style atmosphere where you are provided with all of the comforts of home. Whether it be barbecuing under the covered lanai, or taking a walk to our award winning beaches, there is something here for everyone. A short drive to...
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    Kailua, Oahu 96734
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    510 square feet Apartment with separate bedroom, queen size pull out sofa bed in Living room, washer dryer, full equipped kitchenette, free parking and free Wifi. We offer boogie boards, snorkel equipment, yoga mat, some beach toy's, beach towels, mats and beach chairs. This unique private...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    LOVE RENTALS - FIND YOUR BLISS Ocean-themed studio. Bike to Kailua Town shops, dining, or to the beach! Safe, quiet neighborhood allows for a great experience on your vacation. This studio has a stove top, rice cooker, coffee maker, refrigerator and all things you need to make at-home meals. Relax...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance/Kalapawai Market as well as downtown Kailua. An abundance of shops and restaurants and two of the most beautiful beaches in the world - Kailua and Lanikai Beach – are all in walking distance. Join the...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Terrace
    • Wi-Fi
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Cottage is ideal for a small family and sleeps up to 2 adults and 2 children in a queen-size bed and one twin day-beds plus a futon matress in the living area. After walking down your tropical pathway, enter this gated garden and lanai. The sunny area is filled with tropical flowers - the...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing Mountain Views in a Lush and Peaceful Setting If you appreciate lush and green surroundings you have come to the right place in an exclusive Kailua neighborhood. Kapakai Cottage is a newly renovated modern island style apartment on the second story of our home in Kailua. There are...
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    Kailua, Oahu 96734
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    TAT-*******-7072-01 This property is a legally established dwelling that is rented for period of 30 consecutive days or more at any one time regardless of actual occupancy. Steps from the beach on a private lane in the best neighborhood in Kailua. Large peaceful studio with kitchenette. Close to...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New, light and airy one room cottage with queen sized bed, bath, kitchenette, out door sitting area by the pool. The sun provides for 70 % electricity used in this eco friendly Cottage. The lanai overlooks the tropical garden and the salt water swimming pool. Quiet and peaceful. The unit has...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step back in time and soak up a peaceful, private Hawaiian vacation experience. The Palm Cottage is close to public transport, Kailua city center, Kailua and Lanikai beach an beach park, art and culture. You’ll love this Hawaiian style Cottage because of the high ceilings, the view, the location,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Lanikai studio with stunning ocean view offers the perfect getaway for a single or couple. Ideal for Military personnel transferring to or from O'ahu who need a month or several months rental. Just a ten minute walk to either Lanikai or Kailua Beach, both consistently ranked as two of...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely quiet private studio with gorgeous ocean views from either common deck or your private deck as well as through studio main door. NEW: AC unit for warm nights (although overhead fan is usually all that is needed). Outdoor kitchenette is perfect for travelers with minimal cooking needs....
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *******-6448-01 This property is a legally established dwelling that is rented for period of 30 consecutive days or more at any one time regardless of actual occupancy. This beautiful hillside cottage with stunning ocean view offers the perfect getaway for a couple, small family, or up to four...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A secluded hidden gem, steps away from the beautiful Kailua beach with private beach access. Kailua Ohana Escape is a 3 bedroom, 3 bath family retreat and can comfortably fit 8 people with 2 bunks, a king, 2 queen bed and 1 single bed. One bedroom comes with AC, other bedrooms have either a ceiling...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This air-conditioned Studio is a private retreat away from home. 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, electric frying pan, mixer. Custom...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Private and tropical cottage within easy walking distance to Kailua Beach, Beach Park and Kailua Town. Private entrance & bath, kitchenette. My place is close to public transport and the city center. You’ll love my place because of the location, the people, and the ambiance. My place is good for...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Private Outdoor Pool (Heated)
    • Terrace
    • Parking
    • Wi-Fi
    • Grill
    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 sun provides for 70 % electricity used in this eco friendly Studio It is close to public transport, the city center, Kailua Beach, art and culture. You’ll love my place because of the location...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Terrace
    • Balcony
    • Grill
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take advantage of our vacation rental in Kailua Oahu, and enjoy a family style atmosphere where you are provided with all of the comforts of home. Whether it be barbecuing under the covered lanai, or taking a walk to our award winning beaches, there is something here for everyone. A short drive to...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Nancy's Kailua Cottage Mauka1 / 15
    (8)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 1 March 2019
    This was the ideal spot for us, a pair of retired Canadians escaping a cold winter. Imagine walking just a few blocks to a gorgeous mile-long sandy beach, and just a few more...
    Reviewed 30 December 2018
    This was the perfect cottage for me, my wife and two young sons. She was on a maternity leave and I can work wherever there's Internet, so we relocated our family for six weeks...
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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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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bathroom, Sleeps 4
    Sheffield Suite Walk to Kailua Beach or Town1 / 13
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
    • Parking
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • 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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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
    Beachfront Kailua, Oahu1 / 13
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2018
    My husband and I took our adult children to this beautiful beach front home. On the beach yet set back enough to enjoy complete privacy. The house was perfect for our needs...
    Reviewed 9 April 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua All Taxes Included1 / 62
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2018
    We loved our stay with Patty and she made everything very comfortable and pleasant. We loved the view on the lanai and I would definitely stay there again. Lovely welcome...
    Reviewed 24 May 2018
    Loved staying at Patty & Bob's Kauhale apartment. There are lovely views of the mountains and wonderful breezes throughout the apartment which is very large and comfortable...
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    About this property
    Aloha! We are in compliance with Honolulu City and County Ordinance 18-19 (Bill 89), we welcome 30 day renters. The price is negotiable depending on number of occupants and length of stay. Please email owner for questions, current availability and pricing. Our ohana (family) welcomes you to...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    42 feet from Kailua Beach. Exceptional Extended family Getaway1 / 73
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2019
    Had a wonderful time!Great location, beautiful beach, the house was well equipped for all beach related activities!
    Reviewed 10 June 2018
    We are certainly biased when it comes to ‘beach vacationing.’ We grew making family trips to Myrtle Beach, SC and later to Destin, FL for over 20 years. However, we must say...
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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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed 6 days ago
    This vacation rental is nicely located on a beachfront piece of property. I stayed in the studio that has a view of the mountain and overlooks the pool. While the description of...
    Reviewed 6 July 2019
    This place was wonderful. Quiet and lovely beachfront home. We stayed in the Mountain Suite and took advantage of the saltwater pool with the waterfalls. The only issue was the...
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    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period. It will be available when you arrive. And they are legal - City is closing down illegal vacation rentals. Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
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    • 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
    Oahu Apartment w/ Patio - Steps to Kailua Beach!1 / 24
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2018
    Exceptional hospitality; the owner is on site and very responsive. She greeted us and did everything to make our stay enjoyable. The appartment is well maintained and...
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    About this property
    ** Please note that there is another vacation rental unit on the premises, with a shared yard, and there may be other travelers present during your stay ** Pack your bags and escape to the sleepy beach town of Kailua to stay at this 1-bedroom, 1-bathroom vacation rental apartment. Up to 4 lucky...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Walk to America's best beach. Run around Kailua. Sleep til Noon.1 / 8
    (1)Very good
    Studio, 1 Bathroom, Sleeps 4 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
    Holiday Rental House - 1 Bathroom, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Cable/satellite TV
    • 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
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you...
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    Location Information
    Kailua, Oahu 96821
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Located in the heart of Kailua, one block from a private beach access, our VW Vanagon camper has everything you need to have the most authentic Hawaii experience possible. Stationary unless an additional fee is paid (only for insurance purposes). Comes with access to a 2 man kayak, washer/dryer,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Patio
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    E Komo Mai Private bedrooms are attached ' Ohana' to the main house with private entrance. Home provide a lovely the laid-back Kailua town and the beach lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along with beach...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
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    • Washer
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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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Spacious and inviting one bedroom apartment is on the upstairs of our beautiful Kailua home. With a separate gated entrance, the flat features an outdoor deck surrounded with palm trees and a view of the lush Koolau mountains. The interior is cool and inviting, with plenty of ventilation plus...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful, covered lanai for...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 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 casual Kailua Beach house will transport and inspire you with its panoramic ocean views and is available to be rented for periods of 30 days or more at any one time. All 3 bedrooms, living room and dining spaces offer incredible sites of blue seas and skies, while lush landscaping wraps you...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    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
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    WElCOME TO PARADISE! Kailua is one of the most sought after vacation destinations in Oahu. Kailua is located on the Windward side of Oahu just 12 miles northeast of Honolulu - over Nu'uanu Pali, tallest mountain peak in the Ko'olau mountain range. Kailua offers picturesque, uncrowded beaches, great...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    The best little Kailua beachtown getaway, this is a private apartment on a residential property. All the conveniences you need to make your vacation the best ever, at an affordable price. Privacy, Comfort and Convenience, with attention to details. Walking distance to shopping and restaurants, it...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Mountain Views
    • Washer
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    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A TASTE OF PARADISE LIVING: There is no better way to experience our island lifestyle than living oceanfront in beautiful Lanikai. This property is the perfect destination for capturing all that your hearts and minds conjure up when you dream about tropical paradise living. Your only limitation to...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with a private pool. With 100 feet of...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    1
    Kailua holiday rentals

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

    What to do in Kailua

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

    Renting an apartment in Kailua

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

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