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Beach Rentals in Kailua, HI

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    Travellers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    5 of 5 stars (12) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
    • Balcony
    • Secure Parking
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
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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 96734
    5 of 5 stars Reviewed 16 April 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 3 October 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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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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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 96734
    1 / 24
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Secure Parking
    • Balcony
    • DVD Player
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    • Internet Access
    • Terrace
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    • x
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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 96734
    5 of 5 stars Reviewed 25 October 2015
    Best location - walk to beach, walk to town (many, many restaurants to choose from). Apartment is very clean, modern, and comfortable, pictures are true to experience. Location is...
    5 of 5 stars Reviewed 12 April 2015
    I know people do not want to overstate their claims about their rental property. These accommodations were over the top!. We had friends who lived in the same side of the...
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    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) takes you to our secluded beach... View all property information
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    Kailua, Oahu 96734
    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
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    • Washer
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    • x
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    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 96734
    5 of 5 stars Reviewed 12 April 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 / 15
    4.5 of 5 stars (33) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach.<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 96734
    4 of 5 stars Reviewed 29 May 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...
    4 of 5 stars Reviewed 18 November 2015
    This is a very cute and comfortable room and it was very reasonable for Ohau. My husband and I had stayed right on the ocean and paid a lot more on Kuai, but we were looking for...
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    1 / 13
    5 of 5 stars (1) Excellent
    Private Room, 3 Bathrooms, Sleeps 3 | Quick View
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    • Balcony
    • Air Conditioning
    • Porch
    • Grill
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    • Patio
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    BOOK DIRECTLY THROUGH OWNER AND SAVE 5%! Step back in time and soak up a peaceful, private, quintessential Hawaiian vacation experience. (if this suite is booked, please ask me about our other suites!) Please note we do charge $15 extra per night for a third person. The PINEAPPLE SUITE is a NEWLY... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 12
    5 of 5 stars (5) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Outdoor...
    • Internet Access
    • Waterfront
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    • Mountain Views
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    • Pet-friendly
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    • x
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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 96734
    5 of 5 stars Reviewed 28 December 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 1 November 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 / 7
    4 of 5 stars (1) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
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    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 96734
    4 of 5 stars Reviewed 30 January 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 / 13
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
    • Satellite TV
    • Patio
    • Grill
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Kailua, Oahu 96734
    5 of 5 stars Reviewed 9 April 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 23 March 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 / 21
    5 of 5 stars (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Patio
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    • Outdoor Dining Area
    • Porch
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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 96734
    5 of 5 stars Reviewed 11 March 2016
    Clearly put, Cheryl's Ohana is top of the line. We just got home from a 10 day stay in Kailua at Cheryl's wonderful place. We had read all of her reviews and knew that it would be...
    5 of 5 stars Reviewed 21 July 2015
    We really enjoyed our stay at the House of Serenity! Very close to beaches (not 1, but 3!) and all the amenities available for your use. Cheryl prepared fresh flowers and ice...
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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Shared Garden
    • DVD Player
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    • Washer
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Kailua, Oahu 96734
    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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    • Pet-friendly
    • Child-friendly
    • ?
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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 96734
    3 of 5 stars Reviewed 21 May 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 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Internet Access
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Washer
    • Mountain Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Enjoy the island lifestyle at Mokulua Cottage! This spacious two bedroom, one bath house is perfectly suited for your island getaway. A full renovation was just completed in February 2016, making this home feel brand new! Master bedroom is complete with King sized bed and walk in closet, our guest... View all property information
    Location Information
    Kailua, Oahu 96734
    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 96734
    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 96734
    5 of 5 stars Reviewed 14 March 2016
    Wow! This was the perfect spot for us as we could walk or ride bikes to Kailua beach. The space was clean and adorable with great owners willing to help with anything. Close to...
    5 of 5 stars Reviewed 11 March 2016
    There we were on vacation in paradise, and I got a sinus infection :-( ugg However....we still had an amazing stay!!!! largely due to the comfortable, relaxing, convenient to...
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    1 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Internet Access
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    • Shared Garden
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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
    Location Information
    Kailua, Oahu 96743
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    1 / 35
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    About this property
    A Beautiful Lanikai Beach HouseLanikai Seaside is a luxurious oceanfront home with spectacular views spanning the Mokapu Penninsula, Kailua Bay, Flat Island, Lanikai and the twin Mokulua Islands. From Kailua's iconic turquoise waters, to its white sandy shores to the islands you can almost reach... View all property information
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    Kailua, Oahu 96734
    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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
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    Kailua, Oahu 96734
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    ***Longer minimum stay requirements may apply. Rates may vary depending on length of stay. Inquire for possible DISCOUNTS***Lanikai Beach CottageThe 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 bedroom,... View all property information
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    Kailua, Oahu 96734
    1 / 52
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • ?
    About this property
    The Perfect BlendOhana 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.... View all property information
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    Kailua, Oahu 96734
    1 / 10
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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 96734
    5 of 5 stars Reviewed 6 January 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 / 26
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    • ?
    About this property
    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 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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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 96734
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Charming, Private, Hawaiian Style Home Kai Mele cottage has been featured in Coastal Living as guest house of the month, due to this private Kailua beachfront estate being nestled in among 40+ coconut trees and lush tropical gardens. With over 700 feet of an ancient lava rock wall surrounding this... View all property information
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    Kailua, Oahu 96734
    1 / 22
    4.5 of 5 stars (19) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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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 96734
    4 of 5 stars Reviewed 2 weeks ago
    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 14 May 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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Kailua, Oahu 96734
    1 / 9
    5 of 5 stars (2) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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 96734
    5 of 5 stars Reviewed 20 April 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 29 July 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 / 13
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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 a... View all property information
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    Kailua, Oahu 96734
    5 of 5 stars Reviewed 6 May 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 16 February 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 / 26
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • x
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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 / 20
    6 Bedrooms, 5 Bathrooms, Sleeps 19 | 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
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    Kailua, Oahu
    1 / 31
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Grill
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    • x
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    About this property
    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR 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... View all property information
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    Kailua, Oahu 96734
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    Kailua, Oahu 96734
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • x
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    About this property
    Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means "love," is certainly appropriate for this cottage. From the moment you step inside this spectacular beach-side... View all property information
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    Kailua, Oahu 96734
    1 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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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
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    Kailua, Oahu 96734
    1 / 14
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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 96734
    4 of 5 stars Reviewed 26 February 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 / 45
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    • x
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    The Envy of All ParadisesIn the middle of the great Pacific, on the world's most isolated chain of island, lies a small coastal community that is blessed with heaven-like beauty. LANIKAI, the "heavenly sea". The envy of all paradises. It's crystal clear waters, white sand beaches and lapping shores... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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 96734
    1 / 44
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • ?
    About this property
    Royal Kailua Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green lawn,... View all property information
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    Kailua, Oahu 96734
    1 / 24
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    SWAYING PALMS TAT# W59196922-01 Luxury, custom home with all the amenities, right on the sands of world renowned Kailua Beach. Enjoy a front row seat for spectacular sunrises, sandcastles, kite surfing and more as you unwind and kick back in this special property. Feel the tropical breezes as you... View all property information
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    Kailua, Oahu 96734
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The Pineapple Ohana is situated in a quiet neighborhood where the local experience of the 50th state comes alive daily. Kailua Town and beach are a 3 block walk. Newly remodeled and furnished, this fun house is filled with all the necessary kitchen and bath amenities along with an outdoor grill and... View all property information
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    Kailua, Oahu
    1 / 25
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Welcome to the old Oahu world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870s, he become the contractor of choice for Queen Liliuokalani. Walker erected such notable buildings as the Bishop Museum and Honolulu Hale, or City Hall. John Walker’s inviting and... View all property information
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    Kailua, Oahu 96734
    1 / 26
    5 Bedrooms, 7 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • x
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    • x
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    The Kailua Plantation 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
    1 / 17
    8 Bedrooms, 9 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
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    • Mountain Views
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    • x
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    • x
    About this property
    ROYAL BEACH ESTATE TAT# W54448892-01 Royal Beach Estate is one of the newest , most striking and contemporary executive beachfront estates on world renowned Kailua beach. Constructed in 2008, the estate features two homes (main house and guest house) separated by a resort-style pool with elegant... View all property information
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    Kailua, Oahu 96734
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    This beautiful executive home in the wonderful Lanikai community was newly built in 2014. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the spacious living area is open and flows nicely for family gatherings. The kitchen with custom... View all property information
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    Kailua, Oahu 96734
    1 / 19
    Private Room, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    The lovely Kailua Beachside House is a 2 bedroom 2 bath house that is great for families and couples alike. It's location can't be beat only 2 houses from the world famous white sands of Kailua Beach. This house is perfect for those wanting fun in the sun! On your short stroll back from the... View all property information
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    Kailua, Oahu 96734
    1 / 37
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Grand Kailua Beachside Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green... 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.