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Kailua Vacation Rentals

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    Travelers to Kailua are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 316 Rentals in Kailua
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    Kailua, Cozy, Spacious Duplex Home1 / 69
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Kailua, Cozy, 2 bedroom, Duplex Home1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Lanikai Cottage1 / 13
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Absolutely Oceanfront Kailua Vacation Rental- $1991 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Satellite TV
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Beachfront Plantation Cottage1 / 23
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Satellite TV
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2017
    We arrived and were delighted to discover this special spot ..... Paradise. Exactly how it is depicted in photos - quaint, roomy, well equipped and so beautiful being so close...
    Reviewed November 27, 2015
    We had a marvelous time at this great location. The setting was perfect and the easy beach access and large lawn made for the best vacation in a long time.
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    About this property
    Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Nancy's Kailua Cottage Makai1 / 28
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Parking
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Lanikai Ocean View Retreat1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 18, 2016
    ''High up in the hill'' overlooking the nice Lanekai beach, giving a fresh breeze and the nice sound of the waves on the reefs. It is recommended to have a car. The driveway...
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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...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is...
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    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely hideaway two bedrooms are attached ' Ohana' to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to the attached 2 bedrooms along...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,...
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    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Serenity Beachfront Cottage1 / 8
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    Reviewed February 24, 2017
    This is a modest 2-bedroom, 1-bathroom cottage in a wonderful location. You take exactly 85 steps across the private lawn shown in the PR photo and are on one of the most...
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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...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Private Yard
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a young retired couple with our children all grown up and flown away! So we have decided to rent out the far wing of our home. We are 100 yards from the Ocean, a stroll down the driveway and 4 blocks from beautiful Kailua town where you will find tons of shops, restaurants and a great local...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Theses are the best oceanfront vacation rentals in Kailua. Period... Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean. Both have separate entrances, bathrooms, and full size...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Nancy's Kailua Cottage Mauka1 / 15
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Mountain Views
    • Washer
    • Outdoor Dining Area
    • Patio
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2017
    Nancy's Kailua Cottage is a wonderful place to stay. It was within walking distance to both the beach and Kailua town. The cottage is filled with all the amenities to make your...
    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...
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    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. Tourist License / Licencia de turismo N °: TATax ID #W40799764-01
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    Kailua, Oahu 96734
    Rental Home - 1 Bathroom, Sleeps 4
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    Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!1 / 28
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Patio
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    First let me start by saying the hospitality from Mike and Kelly were above and beyond what I expected. The process was super simple from check in to check out. All texts and...
    Reviewed August 24, 2017
    We loved our stay here! The home was clean and well laid out offering space for our group of 7 adults. Kitchen was clean and well appointed. The beach was just an easy walk away...
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    About this property
    This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor plan offers a serene Hawaiian...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, 1000 sq ft island home in an upscale Kailua neighborhood is your destination for a wonderful Hawaii vacation. Just a 7 minute drive from beautiful Kailua and Lanikai beaches. We offer a spacious master bedroom with a $3,000 California King bed, a second bedroom with a Queen size bed and...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Kailua Beach Cottage 2BD/2BA walk to the beach!1 / 46
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Secure Parking
    • DVD Player
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The cottage was comfortable, clean and equipped with all you need for a great island vacation! Very private. Christine & Frank are lovely hosts and the location is perfect...
    Reviewed August 17, 2017
    Christine and her family made us feel right at home during our four week stay at their beach cottage with our two kids ages 2 & 6. The cottage met all our needs. There were...
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    About this property
    Sandbar Cottage is an immaculate and beautifully appointed 2 bedroom / 2 bath unit located just a short stroll to one of the most beautiful beaches in the world, Kailua Beach. The unit is fully furnished with A/C in all rooms, cable TV, DVD player, Wi-Fi, washer/dryer, access to beach gear. It is...
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    Kailua, Oahu 96734
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay** Escape the hustle and bustle of the city for a revitalizing retreat at this Kailua vacation rental studio with 1-bathroom and sleeping accommodations for 2. This exceptional rental...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Beachfront Hideaway1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 2017
    The house had everything we needed. The home is peaceful. A quick walk across the lawn and you're at the beach. How great is that! Early morning walks and coffee on the beach...
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    About this property
    Be prepared for absolute seclusion, with an electronic gate that opens and closes upon your arrival. Once inside the property, all you will hear are the birds, the sound of the surf pounding, and the rustle of the palm fronds from the many coconut trees on site. The house is right on the beach, and...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Open Air Loft, Steps from beach1 / 32
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
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    • DVD Player
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We spent 11 nights here and could have stayed much longer. With 2 beautiful beaches at the end of the road, fabulous snorkeling and incredible scenery all around, what more...
    Reviewed 4 weeks ago
    If relaxing in calm tropical Hawaiian atmosphere is what you want, look no further. Clean, spacious, nice view, full of cool breeze, kindest owner, and...a few minutes walk...
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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...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Shangri La By The Sea - Stunning views with pool1 / 21
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Description Breath-taking views... luxurious details... this is Shangri-La by the sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this...
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    Kailua, Oahu 96734
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tropical Love Shack One Bedroom Steps to Kailua Beach1 / 16
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    • Satellite TV
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2017
    I researched many hours on several applications before finding this rental as I am a seasoned traveler and naturally want to see everything. Nothing fit my expectations until I...
    Reviewed June 5, 2017
    What an amazing place to be... and when you're there, you feel as though you've been dropped into a very special part of heaven. The setting is truly tranquil, peaceful and...
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    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. Our beautiful, 3 mile stretch of...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tropical Kailua Studio on the Water w/Private Pool1 / 12
    (14)Excellent
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Satellite TV
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 10, 2017
    The location was absolutely perfect! We were minutes away from Lanikai beach, hiking spots, food, and shopping. We were able to escape the people and the hustle and bustle by...
    Reviewed February 22, 2017
    I had a lovely week staying in Jacqui's tropical paradise studio with my husband, and two teen-aged sons. Jacqui went out of her way to make our stay welcoming and comfortable...
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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...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bathroom, Sleeps 5
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    Plantation Charm in Kailua1 / 30
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2016
    The house was beautiful and the pool was an added delight. It was a great place for 7 adults. My only complaint was that the mattress in the master bedroom was so bad I had to...
    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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    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,...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Perfect Oasis, Steps to the Beach!  100% Solar!1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2017
    From the time we made our reservation to our arrival and our stay, it couldn't have been more smooth and enjoyable.The cottage and property was beautiful and was a piece of...
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    About this property
    This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio is detached from the...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hale Maluhia Lanikai1 / 6
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Enjoy the secluded breath taking beach from our fully furnished VERY LARGE 1 BEDROOM, a hideaway for groups from 1-3, our beautiful one bedroom one bath unit is separate and along side of a large 8 bedroom home with a separate entrance from the street, no shared common areas and complete privacy....
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    SUITE ALOHA – Remodeled, Romantic Island Retreat1 / 36
    (19)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    • Porch
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    Pet friendly
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    Reviewed March 18, 2017
    Attractive clean, quiet studio with well-equipped kitchen and bath. Within walking distance of Kailua beach, Kalapawai Market, and Buzz's Lanikai. My wife and I have stayed...
    Reviewed February 19, 2017
    My son and I stayed here in the summer of 2015, and that is all my son has been talking about since.....we are going back this summer to stay in the Aloha Suite for a week and...
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    About this property
    Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find comfort...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Welcome to the most beautiful spots in Hawaii. Perfect location- just 1 min barefoot walk to warm sands and close to Oahu attractions. Comfortable, large studio with king and queen size beds, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes and flat boards....
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to the most beautiful beach in Hawaii. Perfect location-just 1 min barefoot walk to warm sands. Modern , clean, safe and comfortable accommodations close to all Oahu attractions and just 17 min away from Honolulu airport. The 3 bedrooms , 3 bathrooms, the kitchen and the living room condo...
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    Kailua, Oahu 96734
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beachfront Kailua, Oahu1 / 13
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Kailua, Oahu 96734
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Create life long memories and experience Hawaiian local living in the comfortable and beautiful "Kaimana in Kailua". Kaimana (Diamond) in Kailua is a 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in Kailua! The house resides on the...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the most beautiful spots in Hawaii. Perfect location- just 1 min barefoot walk to warm sands and close to Oahu attractions. Comfortable, large studio with king size bed and double futon, kitchenette, AC Free Wi-Fi, parking , laundry, kayaks, snorkeling equipment, bikes, flat boards....
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hale Ohana steps to Kailua Beach1 / 15
    (36)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 21, 2017
    This was like a new hotel room in a private home. We had a separate side entrance. We were within walking distance from the beach, restaurants, and shopping, in a nice...
    Reviewed September 3, 2016
    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...
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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. With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, snorkeling, hiking, and scuba...
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    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Garden Studio1 / 15
    (25)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Outdoor Dining Area
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 5, 2017
    I had a wonderful time staying in this little studio! It's clean and quiet, and I had nightly gecko visitors (which I loved)! The owners are on site, and seemed like very nice...
    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...
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    About this property
    Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or outdoor dining on the lanai....
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    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
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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...
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    Kailua, Oahu 96734
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the one of the most beautiful spots in Hawaii. Far away reef protects us from big waves, white sands invite for long walks on the beach and the ocean calls for all water activities. Prime location, just 2 minutes walk to the beach from the house, close to the airport and all Oahu...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hale Luana1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
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    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Terrace
    • Ocean Views
    • Mountain Views
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one house off of the beach in central Kailua with private beach access 10 steps from your front door, Hale Ina Kalio will enchant you with it's breathtaking views, central yet private location and chic, Hawaii-modern decor. This house just completed a total renovation and is a brand new...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
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    Your Private Place in Paradise - Sleeps 2 to 4!1 / 16
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Kailua, Oahu 96734
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Garden of dreams1 / 15
    (2)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed July 27, 2017
    This place is wonderful! The owners are very welcoming and polite. It was a short distance to the beach and the owners actually have a pool and lounge area that we had full...
    Reviewed July 26, 2017
    Located in a quite area of Kailua, this place is a unique hidden gem. The studio is very comfortable, clean, well equipped with everything you may need for a perfect relaxing...
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    About this property
    Studio with private bath and entrance, air conditioning, internet access, kitchenette, use of pool. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toaster, vegetable steamer,...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Dolphin Studio1 / 10
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed July 5, 2017
    Everything you needed was there. The owners were lovely and a door knock away if you needed help. Everything that was in the pictures was there. The new air con was quite and...
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    About this property
    A comfortable and cozy place to stay with its own entrance and bath. Studio with private bath and separate entrance, AC, close to Kailua Beach Park and Kailua town, very reasonable accommodation. This Studio is furnished with a Queen bed, love seat, table and chairs, TV, AC and ceiling fan. You...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming 1 bedroom  house1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Internet Access
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    • Shared Outdoor Pool (Unheated)
    • Mountain Views
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay. Also note that there are other vacation rentals on site, and other travelers may be present during your stay* For your next Kailua getaway, escape to ‘Tika’s Hale,’ a 1-bathroom...
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    Location Information
    Kailua, Oahu 96734
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Holiday Palms - Private -5 min from Kailua beach1 / 12
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
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    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2017
    This accommodation was very clean and well stocked for day trips whether they be for picnics or a day at the beach! Wonderful
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    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...
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    Location Information
    Kailua, Oahu 96734
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Kailua by the Sea Studio1 / 24
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2017
    Pros: close to a very nice, non busy beach. Very private for being on atop of a homeowners garage. Very Clean and updated. Good location to town and other amenities. Close to...
    Reviewed September 11, 2016
    We have been to Oahu before and it is rare to find such a modern/ updated place to stay. It was clean and so convenient. We had enough toiletries, bath towels etc. for our 3...
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    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...
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sheffield Studio open 8/21-25 9/15-20, 9/27-10/10, 10/17-2010/23-30, 11/11-12/191 / 7
    (2)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2017
    This studio really fulfilled all the expectations that me and my wife have when we are out travelling and searching for good accomodation. Rachel and her husband are very...
    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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    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...
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    Location Information
    Kailua, Oahu 96734
    Private Room - 1 Bathroom, Sleeps 2
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    Kailua Flight and Weather Info
    Airports nearby (1)
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    HNL
    Honolulu Intl Airport
    13.3 miles from Kailua
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    Additional Kailua Info

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    • Local time: 08:28 PM (HST)
    • Peak travel: March - April
    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.

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