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Rentals with Pools in Kailua, HI

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    Travelers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 12
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 23
    5 of 5 stars (5) Excellent
    1 Bedroom, Sleeps 2 | Quick View
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    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Secure Parking
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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
    Location Information
    Kailua, Oahu
    1 / 14
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Secure Parking
    • Grill
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    • Pet-friendly
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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
    5 of 5 stars 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 stars 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 / 21
    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    • x
    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,... View all property information
    Location Information
    Kailua, Oahu
    3 of 5 stars Reviewed May 21, 2016
    Try to arrive during daylight as the lane/driveway to access the rental is a bit tricky. We arrived very late but once we located it we had east access via key in locked...
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    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Kailua, Oahu
    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • Shared Yard
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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
    Location Information
    Kailua, Oahu
    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Grill
    • Mountain Views
    • Patio
    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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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
    4 of 5 stars 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 stars 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 / 24
    4.5 of 5 stars (3) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Washer
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • 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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars 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 / 40
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Child-friendly
    • x
    • x
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    • x
    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
    Location Information
    Kailua, Oahu
    1 / 1
    8 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    Amenities & Details
    • Terrace
    • Private Outdoor...
    • Hot Tub
    • Parking
    • Grill
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Kailua, Oahu
    1 / 20
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Washer
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    5 of 5 stars 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 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Hot Tub
    • Grill
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 luxurious,... View all property information
    Location Information
    Kailua, Oahu
    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 * More... This Hawaii ocean... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars 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 stars (1) Terrible
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Porch
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Kailua, Oahu
    1 / 16
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Air Conditioning
    • Internet Access
    • Sauna
    • Private Outdoor...
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Kailua, Oahu
    1 / 2
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Washer
    • Hot Tub
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 13
    8 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
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