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Holiday Rentals in Kailua

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    ₹ 42,330 Average
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    All 145 Rentals in Kailua
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Plantation Charm in Kailua1 / 30
    (5)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (19)Excellent
    Studio, 1 Bathroom, Sleeps 5 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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    • Wi-Fi
    • Shared Garden
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2018
    We thoroughly enjoyed our time at Hale Ohana. It was the perfect spot to base ourselves as we explored Oahu & it’s beautiful countryside & beaches. Tina is so friendly...
    Reviewed 24 February 2018
    Stayed at Hale Ohana on a girls trip last March (sorry that it took me so long to post this) and we had an awesome time! The location is perfect, close to the most beautiful...
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    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach. With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua, Cozy, Spacious Duplex Home1 / 25
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2017
    We enjoyed our recent stay at the duplex home. The living area is very spacious with a fully stocked kitchen. Owner has done an exceptional job with the lighting and ventilation...
    Reviewed 30 August 2017
    Great place with very helpful hosts. Can't wait to go back! Near a number of excellent beaches and places to see.
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    About this property
    This 850 sq ft duplex consists of a very spacious living room with a vaulted ceiling, 1 bedroom, 1 full bath and a full kitchen with oven. All the areas come with ceiling fans and the home is indirectly ventilated with a whole house fan. The bedroom has a queen bed and comfortably sleeps two...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Kailua, Cozy, 2 bedroom, Duplex Home1 / 30
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2018
    We loved the beaches that are close to this quaint duplex. Everything you need for the beach is provided - boogie boards, sand toys, mats, umbrellas, towels, cooler. We also...
    Reviewed 30 December 2017
    We enjoyed our stay at this place. J &R were great with suggestions and making us feel at home. The location was great, near 2 of the best beaches in Hawaii. When I was told...
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    About this property
    This 850 sq ft duplex consists of a master bedroom with a queen bed and a huge walk-in closet. Access to the full bathroom is through the master bedroom. The other bedroom also has a queen bed. All the areas come with ceiling fans and the home is indirectly ventilated with a powerful whole house...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lanikai Cottage1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Mountain Views
    • Wi-Fi
    • Porch
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 9 April 2015
    Lanikai cottage is less than 1 block from Lanikai beach, with a fantastically equipped kitchen- toaster, blender, mixer etc . There are ceiling fans in every room. Views are of...
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    About this property
    This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Best Location in Kailua! D&D's Cottage1 / 15
    (2)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 28 January 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Garden of Dreams - swimming pool on property -1 / 19
    (9)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 20 November 2018
    i now understand why kiki and joe are spoken of so highly on tripadvisor. welcoming aloha spirit is felt in the cosy unit and in the garden areas.everyone wants to return as...
    Reviewed 21 October 2018
    We enjoyed our stay at the Garden of Dreams. It was cozy, comfortable & clean cottage like studio for two. Away from the busy touristy areas & quite. The closet was...
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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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    Tranquil Tropical Beach Retreat1 / 33
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Balcony
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 October 2018
    Accurate pictures of the property, very clean, and quiet with access to many of the islands neat places to visit. The owner was warm and engaging and provided prompt responses...
    Reviewed 14 March 2018
    We had the most amazing vacation solely due to our hosts, Amber and Matt, in their beautiful guest house. We absolutely had everything available to us that we could think of...
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    About this property
    Come enjoy this two story private Hawaiian style guesthouse in a tranquil setting of tropical flowers and fruit trees. Sip a cup of coffee or glass of wine while you enjoy the view of the Ko'olau mountains and listen to the birds sing from your covered upstairs lanai. Take a dip and catch some...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Affordable Place on the Best Beach in Hawaii1 / 54
    (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 1 February 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tropical Garden Studio - Free Wifi1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 7 September 2018
    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 14 August 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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    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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    Kailua Guesthouse with Pool and Views!1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2018
    We enjoyed our time staying at the guesthouse, the grounds are beautiful and the area is quiet and close to all the things we wanted to see, wish we could have stayed longer. We...
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
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    • 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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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (26)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 13 July 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 24 June 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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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cute Beachwalk Bungalow1 / 20
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
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    • Parking
    • Washer
    • 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
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
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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 3
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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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 5
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    Kailua Beach Aloha Cottage1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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
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    ON BEAUTIFUL KAILUA BEACH1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2018
    Ania, the owner, was friendly and helpful. The location is ideal - just around the corner from a beach with few people and trees for shade. Plenty of restaurants nearby. We had...
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    About this property
    Welcome to the most beautiful spots in Hawaii. Perfect location- just 1 min barefoot walk to warm sands and close to Oahu attractions. Comfortable, large studio with king size bed and double futon, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes, flat boards....
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Terrace
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    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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    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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    Pet friendly
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    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
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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 26 October 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 12 April 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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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 14
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2018
    My wife and i love this place,it is simply beautiful.Great place to relax and enjoy the beach, pool, georgous scenery. The owner is super nice and helpful. We strongly recommend...
    Reviewed 17 June 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...
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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
    Holiday Rental House - 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
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    • Internet Access
    • DVD Player
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 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 8 February 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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    Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!1 / 35
    (5)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had such a great experience! We are 2 families, 1 from Australia with a toddler and 2 teenagers and mine with just our 18 year old son. The layout of the house was perfect as...
    Reviewed 5 July 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...
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    About this property
    This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor plan offers a serene Hawaiian...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy Cottage 5 Minute Walk to Kailua Beach1 / 26
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Garden
    • Grill
    • Cable/satellite TV
    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    We have been to Kailua before and knew we loved the beach park, the Kalapawai General Store and Buzz's Steak House. All three of these were in very quick / easy walking distance...
    Reviewed 1 April 2018
    The cottage is a one bedroom located within walking distance to beach and shopping area that has a variety of restaurants, local stores and chains (Whole Foods and Longs...
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    About this property
    Our 1 bedroom/1 bath Cottage is located on our Ali'i property which is centrally located in Kailua with a short 5 minute walk to one of the top rated beaches in the world Kailua Beach, and a 10-15 minute walk into Kailua town. Our cozy cottage is equipped with king size beds, spacious living room...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Holiday Palms - Private -5 min from Kailua beach1 / 12
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
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    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    This accommodation was very clean and well stocked for day trips whether they be for picnics or a day at the beach! Wonderful
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    About this property
    Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off street parking area for 2 or more...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
    • Parking
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    • Air Conditioning
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    • Outdoor Dining Area
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 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 21 July 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
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Mountain Views
    • Grill
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    • Cable/satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    42 feet from Kailua Beach. Exceptional Extended family Getaway1 / 73
    (5)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 9 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...
    Reviewed 31 May 2015
    Our family got to spend a week in paradise in Dan's home. The view from the lanai is outstanding. Steps to the beach, all the beach and water toys one could ever hope for...
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    About this property
    Our home is located DIRECTLY on the Beach. Arguable the BEST BEACH, the BEST VIEWS, and on the BEST BEACH ACCESS in Hawaii. WONDERFULLY soft and manicured yard. LOTS of TEAK: lounge chairs, rocking chairs, porch swing, picnic tables, and accessories -THE HOUSE: Our home is tastefully decorated...
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    Kailua, Oahu 96734 2324
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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 14 March 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 11 March 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 13 August 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Kehaulani is a stunning luxury villa in Kailua, on the Windward Coast of Oahu, just minutes from the beaches of Lanikai. With spectacular views of the Pacific Ocean and Mokulua Islands, this four-bedroom vacation rental is ideal for families, friends, and destination wedding guests seeking palatial...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Washer
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    • Grill
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    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5-minute drive to the beach. It's just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ONCE YOU VISIT, YOU WILL NEVER WANT TO LEAVE! Beautifully furnished and very spacious. Perfect for the working professional, couple, or 2 singles. Loft in Kailua is just three minutes from world famous Kailua Beach, and the town of Kailua with all of it's fabulous shopping and dining! Includes a...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
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    • DVD Player
    • Cable/satellite TV
    • 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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is inspired in part by those...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach1 / 44
    (22)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
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    • Grill
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2018
    Awesome location-Kailua/Lanikai beach right down the street. Shopping/restaurants right there in Kailua. No need to travel outside Kailua, all inclusive. 4-bedroom home was...
    Reviewed 14 July 2016
    If you're looking for 5 star accomodation, this is not the place for you, however if you want a place to stay that's comfortable in a convenient location, then this will suit...
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    About this property
    A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them....
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description The Ohana Beachfront Villa is a 5-bedroom, 5.5 bathroom estate that offers a great view of Kailua Beach. You can enjoy the view from the ocean lanai and garden lanai, along with the landscaping. One of the best features of this home is a lagoon-style pavilion with tropical waterfalls...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    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
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kailua by the Sea Studio1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 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 11 September 2016
    We have been to Oahu before and it is rare to find such a modern/ updated place to stay. It was clean and so convenient. We had enough toiletries, bath towels etc. for our 3...
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    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach...
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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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