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 Villas in Kailua, Hawaii - Oahu

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 89 Rentals in Kailua
loading...
Sort by
From
£58
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 23 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
£85
Per Night
Studio, 1 Bathroom, Sleeps 3
17 photos Details
Reviews (21) Make Enquiry
5 of 5 stars Reviewed 3 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 2 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
From
£169
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 9
23 photos Details
Make Enquiry
Also consider
Walk to Kailua Beach: Large Studio w/ Kitchenette
1 Bedroom, sleeps 3
£89 / night
Peaceful property in lush tropical setting
2 Bedrooms, sleeps 4
£107 / night
5 minutes walk to Kailua Beach -Kailua Hale Ohana Air Conditioning
1 Bedroom, sleeps 2
£71 / night
Kapoho Hale- Luxury Home on the Water with Amazing Views!
4 Bedrooms, sleeps 9
£611 - £982 / night
From
£338
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 20 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
£491
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
From
£184
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (15) Make Enquiry
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...
5 of 5 stars Reviewed 26 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
£768
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 14
28 photos Details
Make Enquiry
From
£83
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
Make Enquiry
Get the List
From
£120
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 6 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
£476
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
16 photos Details
Make Enquiry
From
£245
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 12
24 photos Details
Make Enquiry
From
£153
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
13 photos Details
Reviews (2) Make Enquiry
5 of 5 stars Reviewed 6 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 1 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
£107
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 2 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
£292
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
14 photos Details
Reviews (3) Make Enquiry
5 of 5 stars Reviewed 17 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
£58
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details
Reviews (2) Make Enquiry
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...
4 of 5 stars Reviewed 2 July 2014
Our studio apartment was very nice. We had a galley kitchen with a full size frig. We also had access to a full kitchen and living room which were common areas. The bicycles...
See all reviews
From
£553
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
10 photos Details
Make Enquiry
From
£1,658
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
16 photos Details
Make Enquiry
From
£307
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details
Make Enquiry
From
£507
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
20 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 26 August 2014
We loved the Kailua home. The home was well furnished and beautiful. The pool and location was amazing. Sheila (owner) was wonderful to work with and accommodating. If you are...
See all reviews
From
£921
Per Night
4 Bedrooms, 11 Bathrooms, Sleeps 6
21 photos Details
Make Enquiry
From
£433
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Make Enquiry
From
£583
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 12
28 photos Details
Make Enquiry
From
£95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
13 photos Details
Make Enquiry
From
£381
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
21 photos Details
Make Enquiry
From
£3,685
Per Night
7 Bedrooms, 8 Bathrooms, Sleeps 14
24 photos Details
Make Enquiry
From
£307
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
8 photos Details
Make Enquiry
From
£461
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Make Enquiry
From
£101
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
30 photos Details
Make Enquiry
From
£117
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
41 photos Details
Reviews (10) Make Enquiry
5 of 5 stars Reviewed 15 May 2014
Bob & Patty made us feel right at home from the time we drove into the driveway. This is a very clean and quite place to vacation. They have everything you would want or need to...
5 of 5 stars Reviewed 12 January 2014
Patty & Bob were such welcoming hosts, it felt like we were visiting old friends. They gave us great tips about local areas and had all the gear (kayaks, paddle boards), etc. to...
See all reviews
From
£92
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
Make Enquiry
From
£243
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
16 photos Details
Reviews (23) Make Enquiry
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...
See all reviews
From
£107
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
15 photos Details
Reviews (2) Make Enquiry
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 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
£399
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
20 photos Details
Make Enquiry
From
£111
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details
Make Enquiry
From
£135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
Reviews (4) Make Enquiry
5 of 5 stars Reviewed 26 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 18 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
£553
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Booking
19 photos Details
Reviews (1) Make Enquiry
5 of 5 stars Reviewed 21 April 2014
We just returned from renting this home in Kailua. We were very happy with the home and the owners. The beach was a very short walk and was not crowded at this end. Kailua is a...
See all reviews
From
£245
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 12
24 photos Details
Make Enquiry
From
£163
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
13 photos Details
Reviews (13) Make Enquiry
3 of 5 stars Reviewed 15 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 22 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...
See all reviews
From
£80
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
18 photos Details
Make Enquiry
From
£829
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
16 photos Details
Make Enquiry
Go to map view
Book Online(40)
Use filters to find the best results!

Suitability

  • Wheelchair access (6)
  • Elder access (26)
  • Suitable for children (29)
  • Pet friendly (2)
  • Smoking allowed (1)

Amenities

  • Internet (78)
  • Grill (67)
  • Other outdoor space (64)
  • Parking (57)
  • Washer/Dryer (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!