Photo by Lisa A Schmidt

Kailua Holiday Rentals

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Our top choices for Kailua holiday rentals

9.6 out of 10, Exceptional, (103)
"The host contacted us ahead of time and had great communication. She provided helpful instructions for finding the property and we enjoyed staying there. "
United States
Amy C.
The price is NZ$512
includes taxes & fees
15 Jan - 16 Jan 2026
Create one of the most unique experiences on the beautiful Lā’ie country side.
10.0 out of 10, Exceptional, (13)
"Quiet, cute & comfortable - we would return to this rental again"
United States
Brandon M.
The price is NZ$1,358
includes taxes & fees
30 Dec - 31 Dec
Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot

Aparthotel in Waikiki

Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (3085)
"Nice spacious rooms with kitchen. "
United States
Izabela
The price is NZ$381
includes taxes & fees
10 Jan - 11 Jan 2026
Aston Waikiki Sunset

Aparthotel in Waikiki

Skyline Island Colony Hotel
3.0 star property
7.2 out of 10, Good, (2139)
"I would definitely look forward to booking my next trip with this hotel "
United States
Louis
The price is NZ$305
includes taxes & fees
6 Jan - 7 Jan 2026
Skyline Island Colony Hotel

Condo in Waikiki

Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (533)
"Very clean, great location, we enjoyed our stay."
United States
Kris Parkinson
The price is NZ$466
includes taxes & fees
9 Jan - 10 Jan 2026
Royal Kuhio
9.6 out of 10, Exceptional, (30)
"everything was great, I'm sure I'll come to this hotel again"
United States
Nazar
The price is NZ$785
includes taxes & fees
10 Jan - 11 Jan 2026
Partial Ocean View Condo with King or Queen Bed and Parking
9.6 out of 10, Exceptional, (140)
"The stay was phenomenal, next time we come hoping you’re available!!"
United States
Brian R.
The price is NZ$467
includes taxes & fees
4 Jan - 5 Jan 2026
Aloha Suite Near the Sea II, 3 Block Walk to Beach
3.0 star property
8.4 out of 10, Very good, (368)
"Everything was great! Mahalo!"
United States
Lynn
The price is NZ$438
includes taxes & fees
6 Jan - 7 Jan 2026
Tropical Studios at Marine Surf Waikiki
2.0 star property
10.0 out of 10, Exceptional, (2)
"This was one of the most reasonably priced places with a kitchenette that wasn't a hostel in Oahu. It came with a few beach items that came in really handy like chairs, boogey board and floaties. The pool was great after spending a day on the beach and they had hot tubs and a bbq area which is great way to save some money. They also had a gym which was 5 for the stay and offered a 5/bag storage fee for the last day which allowed us to enjoy the beach before flying out on the red eye. the...
Canada
Ryan R.
The price is NZ$440
includes taxes & fees
24 Jan - 25 Jan 2026
Remodeled High Floor Waikiki Studio
9.8 out of 10, Exceptional, (186)
"painless entry great location "
United States
Matthew M.
The price is NZ$460
includes taxes & fees
26 Jan - 27 Jan 2026
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
9.8 out of 10, Exceptional, (18)
"Great place, location was great and nice and clean room. The chairs were perfect to bring to the beach as well and the hosts were easy to contact as well"
Canada
Anonymous traveller
The price is NZ$664
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful Studio in the Heart of Vibrant Waikiki!

Apartment in Waikiki

Ilikai Marina Vacations
3.0 star property
8.4 out of 10, Very good, (35)
"Clean and good use of space. "
United States
Cristina Katia Garcia
The price is NZ$616
includes taxes & fees
30 Dec - 31 Dec
Ilikai Marina Vacations

Aparthotel in Waikiki

Aston at the Waikiki Banyan
3.0 star property
7.2 out of 10, Good, (2679)
"Amazing check on smooth friendly amazing room and view will only stay here when I visit now! "
United States
John
The price is NZ$361
includes taxes & fees
11 Jan - 12 Jan 2026
Aston at the Waikiki Banyan
9.6 out of 10, Exceptional, (17)
"It's cozy and perfect for 2 people. There is food truck right across the street . The pool area is really nice with hot tub and bbq area. The beach is just 15 minute walk from this place. "
United States
Shraddha
The price is NZ$464
includes taxes & fees
18 Jan - 19 Jan 2026
A Cozy and Romantic Studio at Heart of Waikiki

Aparthotel in Downtown Honolulu

Bishop Suites At The Executive Centre
4.0 star property
7.8 out of 10, Good, (72)
"After reading the reviews I tried to cancel my reservation but wasn’t able to cancel and I’m SOOOOOOOO happy I didn’t. EVERYTHING that I read was negative about this property turned out quite the opposite! I got two rooms for my wife and kids and we had the upmost best of time! These rooms were like penthouses, clean, wonderful views, spacious and ideally located for our holiday vacation. Excellent value for me and my family!!! "
United States
Maurice
The price is NZ$305
includes taxes & fees
6 Jan - 7 Jan 2026
Bishop Suites At The Executive Centre
3.5 star property
9.4 out of 10, Exceptional, (45)
"Worth it, close to everything and nice views with parking included, a big +"
United States
Boburjon
The price is NZ$746
includes taxes & fees
11 Jan - 12 Jan 2026
High Floor Ocean View Condo (King Bed and Parking)
9.2 out of 10, Wonderful, (44)
"Nice small studio. Views and the breeze coming was great!!!"
United States
Sonika
Renovated Specious Studio with Great View
3.5 star property
8.2 out of 10, Very good, (432)
"The room was very clean and even nicer than I expected. Staff was very friendly and accomodading. Laundry on site was lovely. I loved this place and will be back. Great location. "
United States
Chris Ann
The price is NZ$1,516
includes taxes & fees
11 Jan - 12 Jan 2026
Regency on Beachwalk Waikiki by OUTRIGGER
9.8 out of 10, Exceptional, (27)
"Clean room, good location!"
United States
CHING FEN
The price is NZ$665
includes taxes & fees
10 Jan - 11 Jan 2026
1-bedroom apartment just 5minutes walk to Ala Moana Center
9.8 out of 10, Exceptional, (21)
"Wonderful property. "
United States
Chris T.
The price is NZ$470
includes taxes & fees
24 Jan - 25 Jan 2026
Charming cozy condo in marvelous Honolulu with WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kailua Hotel Reviews

Find out more about Kailua

Everything you need to know about Kailua holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kailua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as NZ$305 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Kailua.

What are some of the best holiday rentals that Kailua has to offer?

BEST LOCATION , LANIKAI registration number W00530010-01 TMK 43005029 Licensed!: This highly rated holiday home rental in Kailua is located in the mountains, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books. Other favourite homes for rent in Kailua are Center of Kailua Bay! Licensed Beach Front Rental #1990/NUC-1774,1775 and Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!.

How many holiday rentals are there in Kailua?

With 153 Expedia holiday rentals, you're guaranteed to find just the right place for your Kailua stay.

What’s there to see and do in Kailua?

Kailua Bay Beach and Kailua Beach are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Ala Moana Center and Waikiki Beach in the wider area.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.