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Beach Rentals and Condos 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.
    1 / 23
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 23
    5 of 5 stars (12) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 24
    5 of 5 stars (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed October 25, 2015
    Best location - walk to beach, walk to town (many, many restaurants to choose from). Apartment is very clean, modern, and comfortable, pictures are true to experience. Location is...
    5 of 5 stars Reviewed April 12, 2015
    I know people do not want to overstate their claims about their rental property. These accommodations were over the top!. We had friends who lived in the same side of the...
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    1 / 15
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed August 6, 2016
    We had a wonderful time at Simone's place. The apartment is very spacious and clean, the ocean really is just a couple of steps away. Simone and her kids are great hosts and were...
    5 of 5 stars Reviewed August 3, 2016
    We are in our 70's... but active... and found Simone and her family and the rental to be perfect for us. It's a 5 minute or less walk to the beach and within walking distance from...
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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C in the bedroom. There is a... View all property information
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    Kailua, Oahu
    1 / 12
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Outdoor...
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    About this property
    Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed December 28, 2015
    We just returned from 10 fabulous days at Jacqui's beautiful island home ... we virtually had the entire place to ourselves for the whole time - spacious suite with tons of shady...
    5 of 5 stars Reviewed November 1, 2015
    Lots of water sport opportunities... kayaking and fishing from the house, not forgetting the lovely pool, and close to excellent beaches for swimming, snorkelling and...
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    1 / 21
    5 of 5 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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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. <BR>Hale Luana, meaning a house to be at leisure and enjoy pleasant surroundings... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed March 11, 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would be...
    5 of 5 stars Reviewed July 21, 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
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    1 / 23
    5 of 5 stars (5) Excellent
    1 Bedroom, Sleeps 2 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
    • x
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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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed March 16, 2015
    One of the very best places we have stayed in Kailua. Great location, fabulous amenities including a full kitchen and use of the swimming pool! Many thanks to our hosts John...
    5 of 5 stars Reviewed February 8, 2015
    Between my husband and I, we have been to many different places throughout the world and this by far was the best vacation EVER....and a huge part of it was due to this incredible...
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    1 / 12
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • x
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    About this property
    Lovely Guest House with lots of upgrades<BR><BR>Large Bathroom with paintings of Lanikai Beach<BR><BR>California King Bed and 60inch Flat-Screen TV<BR><BR>Super Fast High-Speed Internet up to 60MB/s with WiFi Access<BR><BR>Full Kitchen with top of the line appliances <BR><BR>Washer and... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed April 16, 2016
    Private, near the beautiful beach but also close enough to town and shopping, restaurants, etc. The property shows pride of ownership and has most amenities you will need...
    5 of 5 stars Reviewed October 3, 2015
    Wonderful immaculate, quiet, spotlessly clean, idyllic guest bungalow with charming porch and grassy front yard. Walk to Kailua Beach, Kiteboarding, Restaurants, Bike Rental, and...
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    1 / 7
    4 of 5 stars (1) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
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    • x
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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... View all property information
    Location Information
    Kailua, Oahu
    4 of 5 stars Reviewed January 30, 2014
    We were surprised just how spacious this studio is and how nice and fresh it is. Lots of storage and it's well equipped. There were a plate of muffins waiting for us as well as...
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    1 / 8
    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. <BR><BR>Complimentary assigned parking on property and laundry... View all property information
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    Kailua, Oahu
    1 / 17
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • DVD Player
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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    Kailua, Oahu
    1 / 28
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed March 14, 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close to...
    5 of 5 stars Reviewed March 11, 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    1 / 13
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    About this property
    Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground floor unit. The Garden Suite... View all property information
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    Kailua, Oahu
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    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
    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Yard
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    • x
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    • x
    About this property
    Completely Renovated Cottage in Kailua in very close walking distance to the beach.<BR>High Speed Internet with WiFi Access, HD-TV, Oven, Microwave, Toaster, Coffee Maker, Refrigerator, Washer, Dryer, Bathtub.<BR>Eastern King Size Bed and additional sleeper couch for another Queen-Size Bed.<BR>Our... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed April 12, 2016
    This is an excellent rental if you're looking for a place away from the resorts and tourists. Great location with a 5 minute walk to the best beach on Oahu. Plenty of...
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    1 / 9
    5 of 5 stars (2) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Yard
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    • Waterfront
    • Mountain Views
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    • x
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    • x
    About this property
    Airy and bright bedroom with private bathroom in house with resident owner in Kailua. Backyard faces a canal that empties into ocean. Dock and barge boat for afternoon relaxation. Hiking, windsurfing and ocean sports, lovely beaches, and shopping within 2 miles. Waikiki and airport easy to... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed April 20, 2016
    Georgia provided a clean bedroom and bathroom, free access to the common kitchen and living areas, and delightful conversation. We rented her spare vehicle, which was reliable...
    5 of 5 stars Reviewed July 29, 2015
    Georgia T is an excellent host whose hospitality made my stay in Kailua really memorable. As well as the large, en suite room I stayed in, I had access to kitchen, lounge and...
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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
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    • x
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    • x
    About this property
    This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite countertops and all the utensils you... View all property information
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    Kailua, Oahu
    1 / 10
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • ?
    • x
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    • x
    About this property
    Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only 1-1/2 blocks to famous Kailua... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed January 6, 2015
    Happy we stayed here - Janet was friendly and easy to reach before and during our visit. Wonderful place for our staycation! Quiet neighborhood, comfy bed, clean accommodations...
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    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three miles of pristine white sand and... View all property information
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    Kailua, Oahu
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    The majestically beautiful Koolau mountains, palm trees swaying in the distance, beautiful bougainvillea and other tropical flora plus spectacular sunrises are all yours in this large, airy one-bedroom lower level of a two-story home.<BR><BR>Tranquil, and safe, this home is in a quiet residential... View all property information
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    Kailua, Oahu
    1 / 13
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    • x
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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 / 12
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • x
    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... View all property information
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    Kailua, Oahu
    1 / 15
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed May 10, 2016
    Nancy's Cottage was better than we expected, it was new, clean and had all the amenities we needed for our stay. It was also perfectly located, close to the beach and shops. There...
    5 of 5 stars Reviewed August 12, 2015
    Rick and Nancy's cottage is lovely on the inside, newly renovated, perfectly clean, well stocked, w an incredibly comfortable bed. I have back issues and this bed is as comfy as...
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    1 / 15
    4.5 of 5 stars (34) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    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.<BR><BR>With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed 3 weeks ago
    If you choose Hawaii, you have to choose Tina's studio. No wonder celebrities have their vacation at Kailua. The apartment is perfect and the lush garden makes both inside and...
    4 of 5 stars Reviewed May 29, 2016
    The place is in a very good location, you can walk to cafes and restaurants, or the beach. The studio apartment is very nice, with a good bed. We slept very well. But here is one...
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    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    About this property
    Stay like locals! Hotel in Waikiki doesn't excite you? Quiet and beautiful Kailua is the best option for you and your family! We offer a beautiful Hawaiian-theme guesthouse with spacious, 15 ft high-ceiling 2 bedroom, 1 bath with full kitchen where 4-5 people can sleep. One of the rooms have a... View all property information
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    Kailua, Oahu
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute drive. Tradewind Bungalow is the... View all property information
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    Kailua, Oahu
    1 / 21
    3 of 5 stars (1) Average
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kitchen, Patio , BBQ area,... 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 / 13
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
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    • x
    About this property
    Just steps across your private lawn is the deep blue of the Pacific Ocean on Oahu's famed Windward side. Windsurf, boogie board or simply stroll along the beach, it is all right there for you. The house is private and fully stocked with everything you might need for your getaway vacation. From... View all property information
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    Kailua, Oahu
    5 of 5 stars Reviewed April 9, 2016
    We spent a wonderful vacation at this quiet beachfront property. All the little extras were there waiting for us--even down to ziploc bags and paper towels. (too many times we...
    5 of 5 stars Reviewed March 23, 2016
    While this property only rents for a month at a time, it was a great retreat from the world. With private beach access to a wide sandy beach and the wind in the palm trees, you...
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    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Mountain Views
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    • Pet-friendly
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    • x
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    • 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
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    Kailua, Oahu
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    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... View all property information
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    Kailua, Oahu
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
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    Kailua, Oahu
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
    About this property
    This home located can accommodate up to 12 people comfortably and can also be split in half to accommodate smaller parties. Located directly across the street from the Kailua Beach Park and Boat Launch, this modern rebuilt two-story home has a front main house consisting of 4 bedrooms, 4... View all property information
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    Kailua, Oahu
    1 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five bedrooms, including one guest... View all property information
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    Kailua, Oahu
    1 / 22
    4.5 of 5 stars (19) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • x
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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.... View all property information
    Location Information
    Kailua, Oahu
    4 of 5 stars Reviewed July 13, 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 you...
    5 of 5 stars Reviewed May 14, 2016
    This house was everything we saw online. The managers went out of their way to provide us with a VitaMix to make our morning smoothies. We thought there would be bicycles...
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    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
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    • Shared Yard
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    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    • 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
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    Kailua, Oahu
    1 / 1
    8 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Terrace
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    • 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
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    Kailua, Oahu
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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    • x
    About this property
    Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
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    Kailua, Oahu
    1 / 14
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • ?
    About this property
    Lets be honest... one of the main reasons you're visiting Hawaii is for the beautiful weather year round and the jaw dropping beaches. Our vacation rentals are all within walking distance to one of the worlds most beautiful beaches, Kailua beach. Two of our properties (our Awakea & Ali'i... View all property information
    Location Information
    Kailua, Oahu
    4 of 5 stars Reviewed February 26, 2016
    Nice place to stay!!!!! I stayed with my 15 years old son for about 10 days.. This studio was very confortable and very well ubicated, we walk around Kailua from the studio and...
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
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    • x
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    • x
    About this property
    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. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another island. Enjoy panoramic views of... View all property information
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    Kailua, Oahu
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
    Location Information
    Kailua, Oahu
    1 / 10
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
    Location Information
    Kailua, Oahu
    4 of 5 stars Reviewed October 20, 2014
    This is a well appointed, spacious apartment, very close to the beach. Plenty of space for four adults and one small child. Only real negative, is, apart from a small balcony...
    5 of 5 stars Reviewed March 10, 2014
    I have always loved Kailua Beach and the windward side of the island but never stayed there. This bungalow was perfect - easy to find, helpful owners, steps from a path to the...
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    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • ?
    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... View all property information
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    Kailua, Oahu
    1 / 42
    5 of 5 stars (15) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Hawaii GET and TAT ID# OII968I4-OI Our ohana (family) welcomes you to 'Kauhale' our beautiful Hawaiian home. We offer a large cool and breezy 1000 sq ft, 1 bedroom, 1 bath, private, 2nd floor apartment, includes all utilities, located in a great family neighborhood, vaulted open beam ceilings... View all property information
    Location Information
    Kailua, Oahu
    5 of 5 stars Reviewed July 25, 2016
    It was a great stay in Kailua. We were there for a week with 2 of my friends. The place is clean and set up with everything you need. The owners are really friendly and nice. Love...
    5 of 5 stars Reviewed June 21, 2016
    Patty went above and beyond! What a beautiful apartment with everything we could have needed and more. The beds were comfortable and the deck was amazing for my morning yoga as...
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    1 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • ?
    • ?
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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
    Location Information
    Kailua, Oahu
    1 / 21
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Walk to the most beautiful beach on Oahu. Great for large groups up to 12 guests. Koolau Mountain view from upstairs Lanai. The Plumeria Cottage is upstairs has 3 bedrooms, 2 baths and a full kitchen. It has a partial covered 400 sq ft lanai with mountain views. Perfect for relaxing outdoors.... View all property information
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    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...
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    • 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 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • 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 / 30
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This executive beachfront home is right on Kailua Beach. Decorated with island-style rattan furnishings, ceiling fans throughout, cool white tile, and wood flooring. Central air conditioning, wonderful ocean views are just a few of the amenities. The gourmet kitchen comes with granite accents... View all property information
    Location Information
    Kailua, Oahu
    Kailua Vacation Rentals

    Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

    A Kailua Vacation

    Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

    Family-Friendly Kailua

    From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.