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Holiday Rentals and Homes in Kailua, HI

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    Travellers to Kailua are booking December dates now. Secure your holiday 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 (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 15
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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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 6 August 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 3 August 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 / 24
    5 of 5 stars (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
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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... View all property information
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    Kailua, Oahu
    5 of 5 stars Reviewed 2 weeks ago
    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 night...
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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...
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    • Waterfront
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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
    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 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 / 19
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Ocean Views
    • Satellite TV
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    • x
    • x
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    • x
    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 / 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
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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
    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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    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
    • Terrace
    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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 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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    1 / 23
    5 of 5 stars (5) Excellent
    1 Bedroom, Sleeps 2 | Quick View
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    • Private Outdoor...
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    • Air Conditioning
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    • Mountain Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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 17 March 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 8 February 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 / 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
    • Air Conditioning
    • Grill
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    • 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
    4 of 5 stars Reviewed 31 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
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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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    • Secure Parking
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    • Private Garden
    • Satellite TV
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    • Pet-friendly
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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
    Location Information
    Kailua, Oahu
    1 / 28
    5 of 5 stars (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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 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 / 8
    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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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
    Location Information
    Kailua, Oahu
    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
    • Wi-Fi
    • Washer
    • Mountain Views
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 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 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Outdoor Dining Area
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 17
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Shared Garden
    • DVD Player
    • Air Conditioning
    • Internet Access
    • 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
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
    • Parking
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    • Parking
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    • Private Garden
    • Grill
    • DVD Player
    • Wi-Fi
    • Outdoor Dining Area
    Suitability
    • 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
    5 of 5 stars Reviewed 7 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 / 14
    4.5 of 5 stars (24) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Secure Parking
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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 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 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • x
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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 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Patio
    • Satellite TV
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 15
    4.5 of 5 stars (34) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Garden
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 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...
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Grill
    • Balcony
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    • Housekeeping...
    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 21
    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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Kailua, Oahu
    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
    • Wi-Fi
    • Parking
    • 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
    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 / 15
    5 of 5 stars (5) 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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 10 May 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 12 August 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 / 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 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 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    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 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 38
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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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    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
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    Kailua, Oahu
    4 of 5 stars Reviewed 13 July 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 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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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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 / 10
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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 / 28
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how... View all property information
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    Kailua, Oahu
    1 / 14
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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 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 / 10
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Kailua, Oahu
    4 of 5 stars Reviewed 20 October 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 10 March 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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    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
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    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 25 July 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 22 June 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 / 15
    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
    1 / 38
    7 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    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
    1 / 19
    4.5 of 5 stars (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
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    Kailua, Oahu
    4 of 5 stars Reviewed 10 January 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 19 December 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
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Two Bedroom Premium Lockoff Villa An experience in rejuvenation, the 1,311-square-foot, two-bedroom, two-bath deluxe lockoff villa comfortably sleeps eight while providing every amenity necessary for your idyllic retreat in paradise. The two bedroom villa is your personal retreat with 1,311... View all property information
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    Kailua, Oahu
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <BR>Ocean Front House, 2 Bdrm/2 Bath + Ohana Room, Sleeps 4-6. Great outdoor spaces.<BR><BR>Honu Hale Lanikai (Honu means turtle, Hale means house) is a simple and comfortable two bedroom oceanfront vacation home in beautiful Lanikai on the island of Oahu. It has one bedroom/one bath in the main... View all property information
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    Kailua, Oahu
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    ** Please note that the owner of this home lives on the property, in an attached house with its own separate entrance. She's very friendly, but will be extremely respectful of your privacy. She will also serve as your own personal local contact, making it easy to assist you with any questions or... View all property information
    Location Information
    Kailua, Oahu
    Kailua holiday rentals

    Kailua is a town on the Windward Coast of Oahu in Hawaii. The coast in general is renowned as an area of outstanding natural beauty, and Kailua is a great place to see some spectacular sunrises. With some great beaches and a laidback lifestyle, Kailua is the ideal destination for a relaxed family holiday. And with a huge amount of self-catered accommodation available in the town, you can find a home from home in this idyllic island setting. A trip to Hawaii might not sound like a money saving holiday, but there are rental homes available to suit every budget, and free up cash to enjoy the rest of your family holiday.

    What to do in Kailua

    Kailua Beach Park will be the first stop for many tourists, and this amazing ocean beach is bound to take up a few days of your visit. Work on your tan, and admire the sea turtles which can be seen in the area. Also, watersports enthusiasts will love the opportunities provided by Kailua Beach, including kayaking, windsurfing, kiteboarding and scuba diving. All necessary equipment can be hired nearby for some unforgettable holiday experiences. Quite apart from exploring the rest of the Windward Coast and Oahu in general, you will also have to take a boat out to the Mokulua Islands, two small islands just off Oahu's coast which provide great surfing opportunities and slightly less crowded white sandy beaches.

    Renting an apartment in Kailua

    With a huge variety of family friendly rental homes available in and around Kailua, it is easy to find deals on luxurious apartment rentals. With rental costs starting from just £390 for apartments large enough to accommodate a family of four or more, it can work out much less expensive than booking hotel rooms for the entire family. Many of the apartments come with spectacular ocean views, as well as access to private pools, tennis courts and other facilities, so it will certainly not feel like a low cost option! The extra privacy and space that comes with a rented holiday property also means that they're great for kids - the youngest members of your family can run around and let off steam without you having to worry about them disturbing the neighbours!