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Rentals with Pools in Kailua, HI

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    1 / 12
    5 of 5 bubbles (8) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    4 of 5 bubbles (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
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    Kailua, Oahu 96734
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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,... View all property information
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    Kailua, Oahu 96734
    1 / 14
    4.5 of 5 bubbles (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Studio with private bath, private entrance and kitchenette, close to Kailua Beach & Park and Kailua town. The 240 sq foot Studio features a queen bed, pull out sofa bed, table and chairs, ceiling fan, TV, AC and High speed internet access. Pool on property. The kitchenette counter is equipped with... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed May 6, 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a grill...
    5 of 5 bubbles Reviewed February 16, 2016
    We have stayed in the Garden Studio 3 times. We loved it so much we kept coming back. Excellent location, a five minute walk one direction takes you to beautiful Kailua Beach...
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    1 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    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,... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Over the canal, past the boat ramp and round the bend is where you’ll find the Ocean’s Edge in Lanikai. Just a walk on the beach, afternoon swim or bike ride away! This 5 bedroom, 3.5 bath oceanfront home is set dramatically close to and slightly above the ocean’s edge. The living room’s picture... View all property information
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    Kailua, Oahu 96734
    1 / 6
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles 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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    1 / 44
    7 Bedrooms, 8 Bathrooms, Sleeps 15 | Quick View
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    About this property
    The Essence of Kailua Beach Living Castle Point Estateis 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... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***Longer minimum stay requirements may apply. Rates may vary depending on length of stay. Inquire for possible DISCOUNTS*** Lanikai Beach Cottage The charming beach cottage has two separate dwellings on property that are rented together to provide 3 bedrooms and 2 baths. The main house is 2... View all property information
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    Kailua, Oahu 96734
    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    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... View all property information
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    Kailua, Oahu 96743
    1 / 26
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Peaceful Energy of Maluhia Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The covered barbecue lanai area has... View all property information
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    Kailua, Oahu 96734
    1 / 31
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    MINIMUMREQUIREMENTSAPPLY.INQUIREFOR DETAILS. One-of-a-kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical hardwoods... View all property information
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    Kailua, Oahu 96734
    1 / 24
    4.5 of 5 bubbles (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • x
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    • ?
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed July 4, 2012
    Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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    1 / 30
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life will melt away. Most of the... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed August 19, 2015
    Our stay was enhanced by the fact that the owners were available if and when there was any problem. I wondered what I would do if there were an emergency, car problems or medical...
    5 of 5 bubbles Reviewed August 11, 2015
    We have dreamed of going to Hawaii all of our lives and finally had the opportunity to go for our dream trip. I have to say that all of our expectations of Hawaii were filled...
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    1 / 40
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Ohana Beach House is an elegant beach home ideally located just steps from world famous Lanikai Beach. It’s light blue, sea foam green and white-washed wood décor give it a beachy island style, while warm colors, oversized rooms and fine linens give it a cozy and comfortable feel. The home itself,... View all property information
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    Kailua, Oahu 96734
    1 / 19
    4.5 of 5 bubbles (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed January 10, 2014
    Lots & lots of room. Family of 7 - 2 kids (8&10), 2 couples & single. So there was plenty of space that we could stay out of each others hair and off each others nerves. We...
    5 of 5 bubbles Reviewed December 19, 2013
    Our family of four, my friends family of 5 and my Mom and step father stayed here for 10days. I would recommend it. the beds were comfortable, as was the house. There was no air...
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    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 39
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Sauna
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    • x
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    • x
    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... View all property information
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    Kailua, Oahu 96734
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    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... View all property information
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    Kailua, Oahu 96734
    1 / 37
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 32
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    The Paradise Point Estate is a rare jewel that comes fully appointed with Plantation style finishes and furnishings from around the world. Step from a secure entry and motor court into beachfront luxury that whispers old Hawaii, yet offers all of the latest amenities and technologies of a modern... View all property information
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    Kailua, Oahu 96734
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    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... View all property information
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    Kailua, Oahu
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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... View all property information
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    Kailua, Oahu 96734
    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    5 Minute Walk To Beach * Ocean View Beachside Home * Wrap-around Lanai * Spacious 2,200 SF 3BR, 2.5BA Home * Pool * Full Service Gourmet Kitchen * BBQ * Huge Master * Indoor Laundry * TV & WIFI * Parking * 2 Mile Walking Loop * Golf * Hiking Trail * Playground * Park * Also Available 600 SF 1BR -... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed May 9, 2015
    enjoyed to time at the house. fun time with family to relax, sightseeing, beach adventures.... family enjoyed time here.
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    1 / 15
    1 of 5 bubbles (1) Terrible
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • x
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    • x
    About this property
    A very nice updated 5 bedroom home that is located on a side street with no traffic. The beach entrance is a private street entrance 2 blocks away so you can walk to the beach but not have a large crowd of people on the beach. It is a very safe all white sand beach that is great for family's and... View all property information
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    Kailua, Oahu 96734
    1 / 20
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    A Hawaiian oasis awaits you, located on the island of Oahu, just a spectacular 20 minute drive from Honolulu and Waikiki. This Polynesian luxury home is an open and spacious beach house with exquisite tropical decor and high-end furnishings that flow gracefully out to the beautiful covered lanai... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed August 25, 2014
    We loved the Kailua home. The home was well furnished and beautiful. The pool and location was amazing. Sheila (owner) was wonderful to work with and accommodating. If you are...
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    1 / 13
    8 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    About this property
    8 bedroom, 18,000 square feet under roof, main and guest houses, private courtyard, cinema room, full cooking cabana poolside, laid-back luxury at its finest. View all property information
    Location Information
    Kailua, Oahu
    1 / 1
    8 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • x
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    About this property
    Description Tranquility House is located at the east part of the island of Oahu. It is surrounded by lush green mountains and just a few minutes walk to the sandy beach. The property has a peaceful atmosphere. Enjoy relaxing in this fully furnished home with an authentic island style. In this... View all property information
    Location Information
    Kailua, Oahu 96734