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Kailua Vacation Rentals

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    Travelers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 135 Rentals in Kailua
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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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    Cute Beachwalk Bungalow1 / 20
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Hale Ohana steps to Kailua Beach1 / 15
    (38)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Open Air Loft, Steps from beach1 / 16
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Parking
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Simone was a great hostess making herself very available and accommodating to all of our needs including our young kids. we stayed here in 2017 late fall and did have to chase...
    Reviewed August 13, 2018
    This review is from Cecelia and Ronald Tribble's enjoyable family vacation at the Open Air Loft!!The location is great, near the beach and within walking distance, our favorite...
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    About this property
    Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with microwave, hot plate, toaster...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 March 13, 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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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy guesthouse is a separate 2 bedroom cottage located in the back of main house. It is located 1.5 blocks from the beautiful Kailua Beach. On your way to the beach pick up an early morning coffee (they have a variety) breakfast or lunch at Kalapawai Market. You can sit or walk the two and...
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    Kailua, Oahu 96734
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tropical Garden Studio - Free Wifi1 / 17
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Terrace
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    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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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (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 February 9, 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 December 27, 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
    Rental Home - 1 Bathroom, Sleeps 5
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 14
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2018
    Could not have asked for a peaceful and relaxing location! Close to everything yet a world away from Waikiki. Bob & RonI were unobtrusive but available; we were always able...
    Reviewed April 18, 2018
    We loved this little cottage in a quiet neighborhood in Kailua, O’ahu, Hawaii. Bob provides a booklet of necessary information that he titled “Tranquility Base” . It truly is a...
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    About this property
    This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio is detached from the...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Best Location in Kailua! D&D's Cottage1 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2018
    My stay was the perfect vacation. The place is quaint, convenient to everything, and Dayna went way beyond expected in taking care of my needs. I wasn't expecting luxury at this...
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2018
    I took a chance booking this rental for a last minute trip to Kailua to help my son relocate to the area. I have never booked a rental through Tripadvisor before so was a bit...
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    About this property
    Welcome to the one of the most beautiful spots in Hawaii. Far away reef protects us from big waves, white sands invite for long walks on the beach 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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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Garden of Dreams - swimming pool on property -1 / 19
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2018
    This is an attractive, well-maintained, small apartment off the side of the main house where the owners, Kiki and Joe, live, and has its own entrances and access to a private...
    Reviewed June 12, 2018
    I couldn't have asked for a more perfect place to stay on my first solo visit to Hawaii. The neighborhood is very safe and quiet, the property itself has a complete...
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    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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 January 5, 2018
    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 December 29, 2017
    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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    Kailua Beach Aloha Cottage1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    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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    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 Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 27, 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 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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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (25)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 July 13, 2018
    Suite Aloha is a great place to stay while visiting Hawaii. We stayed 8 days, it had everything we needed to make our anniversary stay memorable. Sabine greeted us on our...
    Reviewed June 23, 2018
    Good central location on the east side of Oahu. Near excellent scenic beaches. A few minutes drive to many restaurants. A short drive to several must-see sites.Room is clean...
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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 2 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New, light and airy one room cottage with queen sized bed, bath, kitchenette, sitting area, and lanai. The lanai overlooks the tropical garden with wonderful ocean breezes and the salt water swimming pool. Quiet and peaceful. The unit has parking provided at the front of the house. Swimming pool...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    KAILUA DREAMS-MAKAI:  NEW, LUXURIOUS AND SPACIOUS1 / 23
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2015
    One of the very best places we have stayed in Kailua. Great location, fabulous amenities including a full kitchen and use of the swimming pool! Many thanks to our hosts John...
    Reviewed February 8, 2015
    Between my husband and I, we have been to many different places throughout the world and this by far was the best vacation EVER....and a huge part of it was due to this...
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    About this property
    LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-MAKAI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Banyan Guesthouse is a spacious (400 sq. ft) studio cottage in a private, serene, garden setting a block and a half from world famous Kailua Beach on Oahu's windward side. The former artists studio is newly renovated, beautifully furnished and finished in natural woods. It is very private with off...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Nancy's Kailua Cottage Makai1 / 32
    (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 DREAMS-PALI, the perfect mix of Beach/Town1 / 24
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Balcony
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 25, 2015
    Best location - walk to beach, walk to town (many, many restaurants to choose from). Apartment is very clean, modern, and comfortable, pictures are true to experience. Location...
    Reviewed April 12, 2015
    I know people do not want to overstate their claims about their rental property. These accommodations were over the top!. We had friends who lived in the same side of the...
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    About this property
    LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI is the PERFECT Blend of Town and Beach Living................... Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the world famous...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Hale Maluhia Lanikai1 / 6
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Very spacious, newly renovated, 1-b/1-b suite located just 1.5 blocks away from beautiful Kailua Beach. Enjoy your vacation in our Ohana unit, attached to our home, but with a separate entrance and private/fenced yard, kitchenette, and large living room. You will safe and secure behind our locked...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would...
    Reviewed July 21, 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
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    About this property
    Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. 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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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
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    • 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
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    • Private Yard
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    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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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
    • Internet Access
    • Washer
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    • Grill
    Suitability
    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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Nancy's Kailua Cottage Mauka1 / 15
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Mountain Views
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    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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    Kailua by the Sea Studio1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Balcony
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    • 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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    Holiday Palms - Private -5 min from Kailua beach1 / 12
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
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    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2017
    This accommodation was very clean and well stocked for day trips whether they be for picnics or a day at the beach! Wonderful
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    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Wi-Fi
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    500 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 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, 1000 sq ft island home in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. We offer a spacious master bedroom with a $3,000 California King bed, a second bedroom with a Queen size bed and...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
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    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
    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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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    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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    Pet friendly
    Kid friendly
    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 and queen size beds, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes and flat boards....
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    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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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 24, 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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!1 / 35
    (4)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 July 5, 2018
    Had a wonderful five days in Oahu staying at this gorgeous home just a few blocks from the beach. After a five days in a resort we wanted a more home like setting and privacy...
    Reviewed April 20, 2018
    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.
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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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Peaceful - Romantic - On #1 Rated Beach1 / 20
    (24)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Balcony
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2018
    What a great location! It was an easy walk to the beach. The house had plenty of space for all 12 of us. It is definitely a family friendly house. The house only 4 minutes...
    Reviewed July 18, 2017
    After two years of planning a long overdue family vacation, we decided that renting a house rather than staying at a hotel, was the best choice. After several searches online...
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    About this property
    Welcome to the one of the most beautiful spots in Hawaii! Far away reef protects us from big waves, white sands invite for long walks on the beach, warm ocean calls for all water activities. Prime location, just 2 minutes walk to the beach from the house, close to the airport and all Oahu...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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
    • Cable/satellite TV
    • Patio
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    • Washer
    Suitability
    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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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Washer
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Private Yard
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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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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1
    Kailua Flight and Weather Info
    Airports nearby (1)
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    HNL
    Daniel K. Inouye Intl Airport
    13.4 miles from Kailua
    Low airfares recently found by TripAdvisor travelers
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    Local Weather
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    78° 70°
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    78° 70°
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    76° 68°
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    Additional Kailua Info

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    • Local time: 12:06 PM (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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