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Holiday Rentals with Pools in Kailua

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    ₹ 72,837 Average
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    Travellers to Kailua are booking December dates now. Secure your holiday home today, and have the perfect trip.
    41 Matching Rentals in KailuaView all 130 rentals
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    Tropical Kailua Studio on the Water w/Private Pool1 / 24
    (17)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    Tranquil Tropical Beach Retreat1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 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 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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    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 14 June 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 12 June 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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    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 1 week ago
    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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    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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    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 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
    (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 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...
    Reviewed 21 April 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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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    42 feet from Kailua Beach. Kailua Beach, our Home and yard are looking best ever1 / 73
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    • Mountain Views
    • Children's Pool
    • Cable/satellite TV
    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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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2017
    Beautiful ocean front rental in a quiet neighborhood. Nice pool area. Very relaxing. We enjoyed our 6 night stay very much!
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    About this property
    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period... Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and full size...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lanikai Beach Cottage The main house at Lanikai Cottage includes two bedrooms and one bathroom, a well-equipped kitchen, a dining area, and a living space that opens to the back yard. The guest house contains an additional bedroom and bathroom, as well as a partial kitchen, living room, and lovely...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your White Sand Beach Awaits... Hale Kimo is located just a beach path away from one of the most beautiful beaches in all of Oahu, Kailua beach! The beach has very limited public access, making for an exclusive beach experience on Oahu! This two story custom home is your perfect Hawaiian Hale...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming 1 bedroom  house1 / 12
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2018
    My grand daughter an I had the best time ever!!! Thomas was very nice and the house was perfect, the beach was beautiful . Our stay in Oahu could not have been better!!!
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    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is...
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    Kailua, Oahu 96734
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement elegant indoor and lush outdoor spaces. Live each moment of your relaxing...
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    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Washer
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let the tranquil atmosphere of Maluhia whisk you into vacation mode. A favorite of many celebrities and families for the perfect, peaceful getaway, Maluhia is the definition of island contemporary. Its remodeled, modern interior features nearly 5,000 sq. ft. of living space. The villa also offers...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home Away From Home Nestled in an intimate gated community, Kailua Beach House offers privacy, security and all the comforts you'd look for in an ideal vacation home. Featuring 4 bedrooms and 4 bathrooms on a single level, with an open floor plan that offers pool courtyard views from the kitchen...
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    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how...
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    Kailua, Oahu 96743
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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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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    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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    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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    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    • Parking
    • Waterfront
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it's new...
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    Kailua, Oahu 96734
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
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    Shangri-La By The Sea - Tranquil, Gorgeous Stunning views with pool - ID1 / 21
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description Breath-taking views... luxurious details... this is Shangri-La by the sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,...
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    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    8 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Royal Kailua Estate is the crown jewel of Kailua's beachfront properties. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of over sized stones met with manicured grass provides the driveway that meanders past the luscious green...
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    Kailua, Oahu 96734
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 16
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    Oasis Villa -  outdoor kitchen, pool and jacuzzi - ID1 / 29
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit...
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    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can be divided into three...
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    Kailua, Oahu 96734
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 3 separate living spaces, this remodeled and updated Lanikai home is ideal to accommodate up to 14 guests. The main house of Hale Mokulua - Lanikai consists of 3 bedrooms, 3.5 baths with an open floor plan, high ceilings, hard wood floors, modern kitchen and a wonderful, covered lanai for...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ONCE YOU VISIT, YOU WILL NEVER WANT TO LEAVE! Beautifully appointed two bedroom Hawaiian private residence in quaint Enchanted Lakes. Walking distance to schools, shopping, dining, recreation, entertainment, and fabulous Kailua town. From the koi pond at the front entrance to the swimming pool...
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    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and tropical flowers. The spacious yard is perfect for sun bathing, barbecuing or enjoying your favorite cocktail after a dip in the...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A lush landscape awaits you as you enter this gated tropical paradise tucked away beachside on a private lane, off Kailua Beach. Surround yourself with Hawaiian ambiance and the feeling of an amazing mini resort all to your own. Enter to this impressive 6-bedroom estate home surrounded by exotic...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An ideal layout by famous Architect Peter Vincent provides the perfect place for a work retreat or family gathering. The open-concept floor plan of this magnificent home allows a seamless flow from the fully appointed gourmet kitchen stocked with all the essentials, to the formal dining space, to...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Unforgettable Beachfront Oasis1 / 39
    (8)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2018
    We celebrated our 50th wedding anniversary with our family for two weeks in this beautiful home. We loved the ocean view from the living room, kitchen and master bedroom. We...
    Reviewed 31 July 2018
    Nice family or couples get away. Beds are comfy, pool while not huge did fine for the 12 of us. Beaches close by, easy to get into Waikiki or North Shore.... lots of Ahi Poke...
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    About this property
    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with a private pool, creating a very...
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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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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze! Brand new construction, built in 2017, this home features upgraded appliances and furnishings meticulously hand picked by local designer, Lotus Home Staging, highlighting many beautiful up-cycled, custom...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Place in Paradise - Kailua Beach - Special Fall Rates Available.1 / 29
    (12)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Over 3500 square feet of indoor living area, with TV, Stereo,, DVD, wireless internet, Gas BBQ and outdoor shower make this private, gated property a tropical retreat in paradise. Gracious living and tropical paradise are yours to enjoy in this magnificent Hawaiian vacation home. Designed for the...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GORGEOUS (4B/3B) HOME WITH ATTACHED STUDIO, VERY PRIVATE . ENTIRE PROPERTY SLEEPS 10!!! BRING FAMILY AND FRIENDS ON YOUR HAWAIIAN ADVENTURE!!! NEWLY RENOVATED AND UPDATED. ALL NEW LINENS, TOWELS AND MORE! **********BOOK NOW Specials thru APRIL.....SEE RATES!!!!!*********** **********2014 HONDA...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Fabulous Luxury 5 Bedroom Kailua Beachfront-Private Pool and Spa1 / 24
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    Me and my husband ( grandma and grandpa) and our three adult children, their spouses and their five children just came home from a glorious time in this elegant yet comfortable...
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    About this property
    Three-quarter acre gated estate on Kailua Beach with pool, spa, beach vollyball and unobstructed sunrise ocean views from horizon to horizon. This Luxury Kailua Villa is a fabulous corner of paradise located on world famous Kailua Beach. This property is very secluded, located at the end of a white...
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    Location Information
    Kailua, Oahu 96734
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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