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Vacation rentals in Kailua, HI

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All 108 Rentals in Kailua
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From
$142
Per Night
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1 / 16
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1 Bedroom, 1 Bathroom, Sleeps 2
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$169
Per Night
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1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 4
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$254
Per Night
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 2
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$209
Per Night
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1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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5 of 5 stars Reviewed 9 November 2014
My husband and I stayed at Lanikai Love for 10 days for our honeymoon. We absolutely loved every second of our stay here! The property is exactly as described and even more...
3 of 5 stars Reviewed 20 September 2014
Not pravite pool and hot tub, shared with others lived in that house. No late check out option 11:00 too early. Living room got only fan it's kind hot dining there.
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From
$186
Per Night
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1 / 30
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
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
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5 of 5 stars Reviewed 24 November 2014
I highly recomend staying at one of Nancy's cottages in Kailua. The cottage I stayed in was immaculate and had every amenity you could wish for. The owners have created a true...
5 of 5 stars Reviewed 19 October 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$733
Per Night
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1 / 19
6 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesn’t end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for breakfast... View all property information
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From
$164
Per Night
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1 / 32
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Kailua Cove is a spacious, bright and cheery studio that sleeps 3 and offers: • Private entrance • 1 queen and 1 twin bed • Well-equipped kitchenette, including sink and full-size refrigerator/freezer • Private, indoor washer & dryer • Large walk-in, tile shower • 400+ square feet • Plenty of... View all property information
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5 of 5 stars Reviewed 11 November 2014
I used to live in Kailua, so I feel like I'm a good judge of where you should stay. If you plan on spending a good amount of your time on Kailua or Lanikai Beaches, this is a...
5 of 5 stars Reviewed 31 October 2014
The accommodations were large enough for myself, my husband, and my 20 something daughter. We were staying in Kailua to visit my son/daughter in law. It was clean, comfortable...
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From
$197
Per Night
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1 / 19
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Studio, 1 Bathroom, Sleeps 4
Details Reviews (36) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Cable TV
  • Dryer
  • Internet Access
  • Mountain Views
  • Ocean Views
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Kailua Bay & Mountain Views! Only 100 yards to Kailua Beach Park! This property is located in Kailua, on Windward Oahu. Relax and unwind in this spacious 3rd floor 1000 sq ft studio. Enjoy your morning coffee on the lanai while listening to the breeze, ocean and rambunctious birds. Watch the... View all property information
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5 of 5 stars Reviewed 1 November 2014
best location in o'ahu….. we had a wonderful stay here, we had everything we needed for a perfect vacation. owners were helpful. the place itself is beautiful and spacious…enjoyed...
5 of 5 stars Reviewed 2 June 2014
Just left this morning and hated to leave. The place looks just like the photos. It was very clean and spacious. The outdoor lanai was very nice and spacious as well. The...
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From
$1,410
Per Night
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1 / 24
6 Bedrooms, 5 Bathrooms, Sleeps 15
Details Reviews (3) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
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5 of 5 stars Reviewed 4 July 2012
Stayed one week at this beautiful home. Traveled with 7 adults and 2 teens. Everyone had a room and plenty of space. The home is situated so that breeze flow through out the...
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From
$902
Per Night
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1 / 18
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8 Bedrooms, 4 Bathrooms, Sleeps 18
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu . Surrounded by lush green mountains . The house has tranquil and peaceful atmosphere . This house is fully furnished in an authentic island style. The... View all property information
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4 of 5 stars Reviewed 19 February 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$197
Per Night
View Details
1 / 18
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
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
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5 of 5 stars Reviewed 22 September 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$157
Per Night
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Walk to Kailua Beach or Town. Located at: 131 Kuulei Road Kailua, Hawaii The Ginger Studio at the Hawaii Sheffield House has its own "secret garden" is a delightful home away from home for your Hawaii vacation. The Secret Garden is shaded by a kukui tree and has its own outside dining table and... View all property information
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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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From
$479
Per Night
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Details Reviews (2) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Experience Hawaii at it's fullest by staying at this amazing 1926 bungalow located between two of the most beautiful beaches in the world. Lanikai and Kailua beaches are just 200 yards away. Kayak, Bicycle, Surfboard, Paddle board and Snorkel Rentals are 200 yards away at Kailua Beach Park. A... View all property information
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5 of 5 stars Reviewed 18 July 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$299
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
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3 of 5 stars Reviewed 14 July 2014
First of all, the hosts are friendly and helpful. The location of the villa is very convenient to Kailua Beach. There is also a communal washer and dryer which is very handy to...
5 of 5 stars Reviewed 21 January 2014
Quaint beachy atmosphere. Rooms were clean and well cared for. Charming local decor. Sleeps 4 comfortably. The air conditioner worked perfectly. The kitchen was well stocked with...
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From
$846
Per Night
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1 / 28
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6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Garden
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
$224
Per Night
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-PALI 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 world... View all property information
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5 of 5 stars Reviewed 28 August 2014
We enjoyed our time in Kailua. The apartment was perfect. We had a lot of space and everything was very clean.
4 of 5 stars Reviewed 2 April 2014
My husband and I really enjoyed our stay. The location was great. The air condition was not working. The owner tried to correct the problem twice, but could not repair the...
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From
$338
Per Night
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1 / 14
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1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Bali Hawaii Home is a destination in itself. We built Bali-Hawaii Home with luxury in mind. This is a newly well built home with the best materials.The spacious home with high ceilings was built with inspiration from the modern indoor/outdoor architecture of Bali. Many of our guests are happy to... View all property information
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5 of 5 stars Reviewed 17 November 2014
I love this beautiful retreat! It's so unique, charming, and elegant. I felt so peaceful and relaxed in my own tropical paradise. Thank you! I can't wait to return!
5 of 5 stars Reviewed 20 May 2014
I would highly recommend the Bali House. It had everything that we wanted and needed. It is like staying in your own little resort. The walk to the beach is very easy and...
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From
$446
Per Night
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1 / 16
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3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (23) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Beautiful, licensed, newly remodeled 3 Bedrm, 3 Bath Kailua Beach side villa, surrounded with lush tropical gardens, on private estate with swimming pool and jacuzzi.. Just walk down a private beach lane and in less than 2 minutes you would be at the most beautiful beach in the country! It is a... View all property information
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5 of 5 stars Reviewed 19 April 2014
We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
4 of 5 stars Reviewed 21 November 2013
After 5 weeks travelling in the continental US and Canada with 4 children, we thoroughly enjoyed our week at Kukui House Kailua where we could kick back and relax, enjoy day...
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From
$107
Per Night
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1 / 11
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Mountain Views
  • Pool
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a great 300 sq ft studio only 3 min drive to world famous kailua beach This studio has a cal king bed and a futon that can sleep 4 people 55 in flat screen TV free wi-fi kitchen with everything you need to cook all your meals natural stone shower that is very roomy and a tiled swimming... View all property information
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5 of 5 stars Reviewed 28 September 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
3 of 5 stars Reviewed 6 July 2014
Looking for a deal on our Hawaiian getaway, I booked this place after another fell through. I was trying to be thrifty and this looked like it fit our needs. The place is...
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From
$2,820
Per Night
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1 / 39
6 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Grill
  • Pool
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Description One-of-a-kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical hardwoods and imported stone. Interiors by... View all property information
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From
$130
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
We have 2 properties located directly across the street from one another with two 1 bedroom/ 1 bathroom units between the two properties as well as a two spacious studios & 4 private rooms. All our units have their own private entrances and outside sitting areas. Both these properties are centrally... View all property information
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5 of 5 stars Reviewed 29 October 2014
I really enjoyed my stay here. The location was close to everything. The room was spacious and clean. The bed was super comfortable. The deal was amazing. I certainly would book...
5 of 5 stars Reviewed 28 August 2014
This studio is very roomy and comfortable with everything needed for a great stay! We did a lot of site seeing on the island, and it was so refreshing to come back to our studio...
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From
$322
Per Night
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1 / 26
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7 Bedrooms, 5 Bathrooms, Sleeps 20
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Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
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4 of 5 stars Reviewed 25 August 2014
Brenda and her co-Horts were so great to work with and very attentive to our needs and request. We had 10 of us and they helped coordinate all the space and rooms we needed to...
5 of 5 stars Reviewed 11 June 2014
We stayed in Palawiki properties with 3-bedroom 2 bath room. The house is spacious , beautiful, lovely and very clean. It is more like a sweet home to my family. The kitchen...
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From
$168
Per Night
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1 / 12
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Studio, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Private Outdoor...
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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
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From
$508
Per Night
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1 / 10
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
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... View all property information
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From
$874
Per Night
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1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Kakela Kai is a well-maintained, nicely furnished four bedroom, three bath contemporary home with den and approx. 2,200 sq. ft. located in a security-gated neighborhood near the center of Kailua Beach. High ceilings and sliding glass doors in the main living areas provide a feeling of spaciousness... View all property information
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From
$147
Per Night
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1 / 18
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning studio. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$169
Per Night
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1 / 15
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
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From
$186
Per Night
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1 / 11
Payment Protection
Studio, 1 Bathroom, Sleeps 3
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just minutes away from the beach by foot or bike. Kailua Seahorse Studio is PERFECT. It's even more beautiful in person than in the pictures.... View all property information
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From
$196
Per Night
View Details
1 / 12
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Grill
  • Internet Access
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Hawaii Sheffield House is located only 10 houses to Kailua Beach. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite has free off street parking, free wifi, cable TV, boogie boards and a first morning complementary continental breakfast. The... View all property information
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From
$1,354
Per Night
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1 / 24
Payment Protection
5 Bedrooms, 6 Bathrooms, Sleeps 14
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Casual accommodations located on Kailua Beach, voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit. Large outdoor deck spaces provide the perfect place to relax in the sun or enjoy a... View all property information
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Studio, 1 Bathroom, Sleeps 3
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  • Safe
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  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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About this property
E Komo Mai! (welcome) Your memorable stay starts as you drive down your private lane into the serenity of a tropical outdoor paradise, providing you with the ultimate island vacation location. Staying true to its Hawaiian charm the 3 bedroom 2 bathroom main home and 1 bed 1 bath separate cottage... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Beautiful Single Family Home is sought after neighborhood in Kailua. 15 minutes walk to the beach, Fully furnished with dishes, linens, kitchenware - everything you need. Accommodates 4-6 Some standout features are -- -- 2270 sq feet of house plus a yard that is about 1800 sq feet. -- beautiful... View all property information
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6 Bedrooms, 3 Bathrooms, Sleeps 10
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  • Private Outdoor...
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesnt end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for... View all property information
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Come experience the beauty and magic of Kailua. Stay in our charming, hawaiiana Hale Nalu Palekaiko, Surf Paradise Hale...See why people call Kailua papalani, heaven on earth. Relax in our comfortable and welcoming hale. The main house has three bedrooms, 2 bathrooms, living, dining and lanai... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Mountain Views
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
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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1 Bedroom, 1 Bathroom, Sleeps 3
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  • Pets allowed
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  • Suitable for children
  • x
  • x
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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... View all property information
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Air Conditioning
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  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Hale Maluhia (House of Serenity) is a kama'aiana style home near Kailua Beach. In a quiet Kailua neighborhood, the home is a quick 5 minute, one block walk to the world famous secluded white sand beach. Relax with friends and family in this child-friendly family home. Experience the warm "old... View all property information
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Mountain Views
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with well quality furniture (Koa). Makana's Place features a full kitchen plus... View all property information
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
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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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Studio, 1 Bathroom, Sleeps 3
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  • Suitable for children
  • x
  • x
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  • Elder access
  • x
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. Complimentary assigned parking on property and laundry... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Mountain Views
  • Private Outdoor...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
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... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Dishwasher
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  • Mountain Views
  • Private Outdoor...
  • Satellite TV
  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Endless Summer Getaway.... the name says it all. This fabulous upgraded three bedroom three bath home boasts pride of ownership along with a feeling of hospitality. As you enter into the home you walk into the living/family room, then straight ahead is the sliding door that leads to the outdoor... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Grill
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
You will find Serenity here. This is the beachfront cottage you've been searching for.This delightful cottage is found in the middle of stunning Kailua Beach. Casually lounge in the small but cozy living room and be astounded by breathtaking views of the beach. Step out your front door and onto... View all property information
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4 of 5 stars Reviewed 21 August 2013
Our family (children age 11 and 9) stayed here for our summer vacation. The location is about as perfect as you can get. A short walk across the lawn right onto one of the most...
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5 Bedrooms, 3 Bathrooms, Sleeps 10
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Hawaiian Paradise, across the street is a short path to Kailua Beach, voted #1 beach in America by Conde Nast Traveler Magazine. A beautiful rather secluded beach far less crowed than most beaches in Hawaii. This private home is a home away from home. This 3 bedroom, 3 Bath property is completely... View all property information
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Studio, 1 Bathroom, Sleeps 2
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  • Pets allowed
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  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Enjoy peace and quiet in this quaint, private cottage with queen-size bed and kitchenette, lovely tropical yard with covered lanai, beach shower, and 1-1/2 blocks to famous Kailua beach. Walking/biking distance to boutiques and restaurants in Kailua town. There is a washer/dryer on premises and... View all property information
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This three bedroom Lanikai home, plus attached, but private entrance to a completely self contained studio with kitchenette and fully enclose courtyard, is just one short block to Lanikai Beach. Bring the family, and let the grandparents, friends be with you but also have the privacy they need! We... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Blossoms, palms and tiki's welcome you as you enter the 1/4 acre property tucked away beach side on a private lane. This spacious home is surrounded by exotic tropical gardens, and is just steps to Kailua's beautiful beach, 75 yards via private right of way. We offer a two bedroom rental unit... View all property information
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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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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.