We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Kailua, HI

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 95 Rentals in Kailua
loading...
Sort by
From
$6,269
Per Night
10 Bedrooms, 11 Bathrooms, Sleeps 18
37 photos Details Reviews (4) Make Enquiry
From
$188
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
30 photos Details Reviews (1) Make Enquiry
From
$1,026
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 14
24 photos Details Reviews (12) Make Enquiry
Also consider
Quaint tropical cottage walk to beach covered lanai
Sleeps 2
$108 / night
Beautiful Lanikai Home
3 Bedrooms, sleeps 8
$484 / night
Coconut Cabana: Designer Studio AC Pool near beach
Sleeps 2
$148 - $182 / night
Kailua Beach Escape, Full Size Pool
5 Bedrooms, sleeps 13
$513 - $912 / night
From
$199
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (1) Make Enquiry
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...
See all reviews
From
$227
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
15 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 22 September 2014
We were a bit apprehensive about being the first renters of this new rental, but took a chance since the location and space seemed ideal. We had a wonderful week staying here...
See all reviews
From
$393
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details Reviews (7) Make Enquiry
4 of 5 stars Reviewed 22 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...
See all reviews
From
$541
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 18 August 2014
We stayed here for 7 nights during June of this year. The house was exactly what we were looking for. The location is ideal as it is not more than 1 minute walk from the beach...
See all reviews
From
$912
Per Night
8 Bedrooms, 4 Bathrooms, Sleeps 18
18 photos Details Reviews (3) Make Enquiry
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...
See all reviews
Get the List
From
$144
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 8 July 2014
We enjoyed staying in this neat and clean studio apartment. Sabine and Ray were welcoming and have put a lot of thought into providing everything for guests' comfort. We loved...
4 of 5 stars Reviewed 28 June 2014
We spent 6 nights at Suite Aloha at the end of April. The studio apartment was very clean, nicely furnished and decorated in Hawaiian style. We made use of the large gas barbecue...
See all reviews
From
$204
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
15 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 29 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 3 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...
See all reviews
From
$158
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Enquiry
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...
See all reviews
From
$108
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 29 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 7 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...
See all reviews
From
$171
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
18 photos Details Reviews (9) Make Enquiry
4 of 5 stars Reviewed 14 August 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
5 of 5 stars Reviewed 9 January 2014
This proved a really great choice , the condo is lovely and in a really quiet and peaceful area. Plenty of space and a nice garden with plenty of seating . The owner lives next...
See all reviews
From
$1,510
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 14
29 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 9 April 2013
Wonderful location right on the beach and perfect home to celebrate my birthday with all 16 members of my family. Decor was a little dated but adequate. Loved being on the beach...
See all reviews
From
$222
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details Reviews (6) Make Enquiry
5 of 5 stars Reviewed 7 August 2012
This cabana is in a great location if you are looking for something peaceful and relaxing. We stayed over a weekend after being in Waikiki the week prior, and it was a delightful...
5 of 5 stars Reviewed 7 February 2012
We really enjoyed our short stay at Julie's Cabana. It is beautifully decorated and she made us feel especially welcome with a basket of local goodies and ideas and directions to...
See all reviews
From
$1,425
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 15
24 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 5 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...
See all reviews
From
$199
Per Night
Studio, 1 Bathroom, Sleeps 4
19 photos Details Reviews (34) Make Enquiry
5 of 5 stars Reviewed 3 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...
4 of 5 stars Reviewed 3 March 2013
It was an easy drive from Honolulu Airport with wonderful access to beautiful beach - 3 minutes' walk down the hill to the park. Accomodations were very comfortable (especially...
See all reviews
From
$251
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 27 March 2013
This place was just as described, lovely! Peaceful, accommodating and very clean. The owners were very pleasant. We would recommend this place to anyone. It really...
4 of 5 stars Reviewed 19 January 2012
We stayed here for a couple of nights while visiting our son who lives in Kaneohe. The apartment lives up to the pictures shown on TripAdvisor. We were in the one on the ocean...
See all reviews
From
$376
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
14 photos Details Reviews (5) Make Enquiry
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...
4 of 5 stars Reviewed 8 April 2014
Bali Hawaii was spacious and nicely appointed. The three of us had plenty of space to spread out and have privacy. What I liked best was the location--a 5 minute walk to the beach...
See all reviews
From
$1,425
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 19 June 2014
Kailua is a quiet community with a small town feel. It has one the largest most beautiful beaches on Oahu. More peaceful and less crowded than Waikiki. Great hosts at...
See all reviews
From
$108
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details Reviews (18) Make Enquiry
5 of 5 stars Reviewed 4 July 2014
The place is a large room for 2 people with AC if you need it. They provide internet service for free. The kitchen is small but will full fill your needs. I would stay here...
5 of 5 stars Reviewed 24 April 2014
We stayed here for 3 days. The studio was clean and very nicely decorated. The small kitchen had everything you would need to cook or prepare meals. Plenty of towels, pillows, and...
See all reviews
From
$284
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
13 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 7 September 2014
We just got back from a weeklong stay at Surf house, and it was perfection. Everything from the beginning till the end has been easy and smooth. Julie, the real estate agent who...
5 of 5 stars Reviewed 2 June 2014
First let me say working with Julie has been easy as pie, from her professional help to her amazing taste and recommendations while on Oahu she has helping make the process of...
See all reviews
From
$627
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 15 April 2014
If you like falling asleep to the sound of the ocean, taking long walks on a soft sand beach or relaxing in the hammock on the lawn, this is the place for you!. Our family of four...
5 of 5 stars Reviewed 21 October 2013
Very nice place for our family since the children are small and can sleep on the couch. The parking is tight. The house is truly right on the beach. A mile from "downtown" Kailua...
See all reviews
From
$165
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details Reviews (16) Make Enquiry
4 of 5 stars Reviewed 8 September 2014
We rented the jungle studio that had one full size bed and a futon. The location is awesome and the room was clean. Located right across the street from Kalapawai Market where...
4 of 5 stars Reviewed 25 May 2014
We were very pleased with our individual units. We had a spacious studio with large closet and great bathroom. Full size fridge but no stove/oven. They did provide a hot plate...
See all reviews
From
$2,223
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 7
22 photos Details Reviews (1) Make Enquiry
From
$512
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
16 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 19 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...
See all reviews
From
$1,197
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
31 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
The pictures do not provide justice to the true beauty and convenience of the yard and beach. It is spectacular! The house is large and comfortable . It worked well for my...
See all reviews
From
$313
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 9
23 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 9 October 2014
Thank you for this wonderful stay, in my language I say, U Siyam, utmost respect of thank you! It was a comfortable little cottage that suit my entire family of 9, WOW! Incredible!
See all reviews
From
$5,585
Per Week
6 Bedrooms, 3 Bathrooms, Sleeps 11
16 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 13 September 2014
We could not have been happier with this house. It was absolutely perfect for what we wanted, which was time together, easy beach access, fun for all. The house is beach casual...
5 of 5 stars Reviewed 21 April 2014
nice house and property right on kailua beach. perfect beach for the whole family. great boogie boarding, surfing down the way, nice long walks. bike rides into town
See all reviews
From
$131
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (19) Make Enquiry
5 of 5 stars Reviewed 15 August 2014
Perfect location away from all the noise of waikiki on in our opinion the best part of Oahu. The local beaches are perfect and Tina is really helpful if you need any info :)
5 of 5 stars Reviewed 17 February 2014
If you want to stay away from Waikiki, try here. Easy walking distance to lovely beaches and everything you need. Make coffee there or take a short stroll to the Kalapawai market...
See all reviews
From
$114
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details Reviews (29) Make Enquiry
4 of 5 stars Reviewed 3 September 2014
Sharon's Serenity Bed & Breakfast is located within walking distance of beautiful Kailua Beach, one of the nicest beaches we visited while in Hawaii. As promised, Casey the Bichon...
5 of 5 stars Reviewed 8 February 2014
Sharon is a gracious accommodating hostess. She made my stay very pleasant and rejuvenating. I highly recommend her home - she has 2 Bichon dogs who are friendly and quiet. I...
See all reviews
From
$199
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
11 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 1 February 2014
We had a wonderful ten-day stay at Maunawili House with our family. The house was spacious, clean and comfortable, and the owners were helpful and welcoming. We loved being...
5 of 5 stars Reviewed 2 October 2013
Maunawili House is comfortable, spacious and well equipped. Beautiful views, quiet, and completely off the beaten path. Close to hiking trails, close enough to beaches, shopping...
See all reviews
From
$342
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Reviews (15) Make Enquiry
5 of 5 stars Reviewed 11 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...
5 of 5 stars Reviewed 27 April 2012
Having recently returned from our holiday in Hawaii we are so missing Kailua and wish we were back! Our holiday was fantastic the apartment was a great place to stay it...
See all reviews
From
$131
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
23 photos Details Reviews (4) Make Enquiry
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...
4 of 5 stars Reviewed 11 August 2014
We were 4 people (including a 9y old boy) staying 4 nights in this unit. It is nicely located in a quiet area, clean, and well decorated. There's a flat screen TV (we didn't use...
See all reviews
From
$182
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
28 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 15 May 2014
Great & relaxing place to stay, especially sitting in the yard for breakfast, using the BBQ or just hanging around reading and sipping some wine. Reservation is swift, Jenny is...
See all reviews
From
$741
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
19 photos Details Reviews (3) Make Enquiry
4 of 5 stars Reviewed 11 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 20 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...
See all reviews
From
$792
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
26 photos Details Reviews (22) Make Enquiry
5 of 5 stars Reviewed 26 August 2014
This is a lovely and comfortable home, just steps from Kailua Beach, that will give any traveler a wonderful taste of Hawaii. We walked the beach every morning, spent time in the...
5 of 5 stars Reviewed 8 July 2014
We rented the house for a family vacation and to attend our son's wedding wedding. It was everything we could of wanted. No surprises and in excellent condition. Great location...
See all reviews
From
$325
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
Bookings
26 photos Details Reviews (13) Make Enquiry
4 of 5 stars Reviewed 26 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 12 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...
See all reviews
From
$165
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
32 photos Details Reviews (11) Make Enquiry
5 of 5 stars Reviewed 10 October 2014
We spend some days with our little son at Marias' appartment. It is perfectly equipped and situated very close to the beach. Kailua is a great place to stay with some nice...
5 of 5 stars Reviewed 4 May 2014
My wife an I enjoyed our 5 day stay so much. The area is beautiful and quite compared to Honolulu. The local town has some great places to eat and the people are very friendly...
See all reviews
From
$158
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details Reviews (21) Make Enquiry
5 of 5 stars Reviewed 4 September 2014
This great little find is located 45 seconds from one of the best beaches in Oahu. It's 5 mins from central Kailua (shops, restaurants, conveniences), and has parking. The place...
5 of 5 stars Reviewed 3 June 2014
Cozy, wonderful studio, best location, just 3 minutes walk from one of the most amazing beaches in the world. Hosts were very helpful and friendly at all times. Looking forward to...
See all reviews
Go to map view
Book Online(43)
Use filters to find the best results!

Suitability

  • Wheelchair access (9)
  • Elder access (27)
  • Suitable for children (35)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (78)
  • Grill (70)
  • Other outdoor space (64)
  • Washer/Dryer (58)
  • Parking (54)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
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!