A couple sitting on a beach with clear blue water and small islands in the distance.

Kailua Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kailua holiday rentals

1. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.4 out of 10, Good, (2,796 reviews)
"Staff are really nice & friendly."
United States
Josephine
The price is NZ$385
includes taxes & fees
4 Dec - 5 Dec
Aston at the Waikiki Banyan

2. Bishop Suites Downtown Honolulu

Bishop Suites Downtown Honolulu
4.0 star property
Downtown Honolulu
7.6 out of 10, Good, (170 reviews)
"The property had beautiful views in Honolulu"
United States
Aftan
The price is NZ$410
includes taxes & fees
10 Nov - 11 Nov
Bishop Suites Downtown Honolulu

3. soulfactory Hawaii

soulfactory Hawaii
3.0 star property
Waikiki
10.0 out of 10, Exceptional, (1 review)
"Distance to the Shops and beach is nice. The remote check-in was easier to access."
United States
Emily
The price is NZ$347
includes taxes & fees
14 Nov - 15 Nov
soulfactory Hawaii

4. Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
Waikiki
9.8 out of 10, Exceptional, (217 reviews)
"Great price and location. Clean and enjoyable"
United States
Ashlyn G.
The price is NZ$462
includes taxes & fees
11 Nov - 12 Nov
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

5. Newly Renovated · Ocean View Corner Studio · King Bed · Walk to Beach

Newly Renovated · Ocean View Corner Studio · King Bed · Walk to Beach
Waikiki
9.4 out of 10, Exceptional, (44 reviews)
"Great studio with an amazing view! Super happy with everything & would definitely stay again!"
United States
Emily B.
The price is NZ$496
includes taxes & fees
16 Nov - 17 Nov
Newly Renovated · Ocean View Corner Studio · King Bed · Walk to Beach

6. Modern, renovated studio in Waikiki

Modern, renovated studio in Waikiki
Waikiki
9.2 out of 10, Wonderful, (118 reviews)
"Great location. Excellent views from the 29th floor room. Excellent communication. Kitchen facilities available. Close to convenience shops 7/11 and ABC."
Australia
Cindy
The price is NZ$363
includes taxes & fees
13 Nov - 14 Nov
Modern, renovated studio in Waikiki

7. Aloha Suite Near the Sea III - 2 Block Walk to Beach!

Aloha Suite Near the Sea III - 2 Block Walk to Beach!
Waikiki
9.8 out of 10, Exceptional, (129 reviews)
"Clean, had everything i needed, and even had beach chairs to borrow. Super close to rhe beach and owner was very communicative and made checking in and out easy!"
United States
Sarah
The price is NZ$480
includes taxes & fees
10 Nov - 11 Nov
Aloha Suite Near the Sea III - 2 Block Walk to Beach!

8. Hotel Suite in Waikiki, near the beach

Hotel Suite in Waikiki, near the beach
Waikiki
9.2 out of 10, Wonderful, (34 reviews)
"great stay. excellent location. very helpful owner. highly recommended."
United States
Darren L.
Hotel Suite in Waikiki, near the beach

9. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,317 reviews)
"Great place"
United States
Iurii
The price is NZ$310
includes taxes & fees
16 Nov - 17 Nov
Skyline Island Colony Hotel

10. Affordable Luxury in Waikiki

Affordable Luxury in Waikiki
Waikiki
9.2 out of 10, Wonderful, (44 reviews)
"Cute little spot. Clean room, Close to everything, and valet made it easy to get in and out"
United States
Victoria O.
The price is NZ$508
includes taxes & fees
16 Nov - 17 Nov
Affordable Luxury in Waikiki

11. Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.6 out of 10, Excellent, (59 reviews)
"Great stay enjoyed everything about it"
United States
Johnathan
The price is NZ$645
includes taxes & fees
26 Nov - 27 Nov
Ilikai Marina Vacations

12. Island Colony (IC14)

Island Colony (IC14)
Waikiki
9.2 out of 10, Wonderful, (69 reviews)
"Perfect apartment for 3 adults. Plenty of room and amazing balcony. Comfortable sofa and good amenities. I will miss this place."
United States
Nevena
Island Colony (IC14)

13. Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (638 reviews)
"Great stay and location."
United States
Armando
The price is NZ$449
includes taxes & fees
10 Nov - 11 Nov
Royal Kuhio

14. Corner Unit Studio@Waikiki Hotel Building 1 day min

Corner Unit Studio@Waikiki Hotel Building 1 day min
Waikiki
8.2 out of 10, Very good, (108 reviews)
"Good location, easy check in and out"
United States
Manuel
The price is NZ$450
includes taxes & fees
11 Nov - 12 Nov
Corner Unit Studio@Waikiki Hotel Building 1 day min

15. Partial Ocean View Condo with King or Queen Bed and Parking

Partial Ocean View Condo with King or Queen Bed and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (44 reviews)
"Clean room, excellent view, close to beach and shopping. Friendly staff. Highly recommend!"
United States
Susan
The price is NZ$872
includes taxes & fees
20 Nov - 21 Nov
Partial Ocean View Condo with King or Queen Bed and Parking

16. King Bed • Renovated • Canal & Mountain View • Walk to Beach

King Bed • Renovated • Canal & Mountain View • Walk to Beach
Waikiki
9.6 out of 10, Exceptional, (72 reviews)
"Very clean room ,comfy bed ,aiir condition a little noisy ,perfect room for couple,communication with Yuan was very good,very good location ."
United States
Bruno L.
The price is NZ$499
includes taxes & fees
10 Nov - 11 Nov
King Bed • Renovated • Canal & Mountain View • Walk to Beach

17. Renovated Specious Studio with Great View

Renovated Specious Studio with Great View
Waikiki
9.0 out of 10, Wonderful, (53 reviews)
"Ash was excellent in communicating. He even allowed us early entry which was so appreciated as we had flown from Calgary to Vancouver to Honolulu and were very sleep deprived!"
Canada
John
The price is NZ$363
includes taxes & fees
10 Nov - 11 Nov
Renovated Specious Studio with Great View

18. Luana Waikiki by Tropical Escapes Realty

Luana Waikiki by Tropical Escapes Realty
2.5 star property
Waikiki
8.0 out of 10, Very good, (67 reviews)
"We loved our stay at the Luana Waikiki. The concierge was always polite. The check in process was easy. We were surprised with all the extra cool lights in the room. We thought the bed was very comfortable and the room was clean. It's a fairly short walk to Waikiki beach and there are food trucks right across the street."
United States
Kate Elizabeth
The price is NZ$821
includes taxes & fees
12 Nov - 13 Nov
Luana Waikiki by Tropical Escapes Realty

19. Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi
Waikiki
9.0 out of 10, Wonderful, (137 reviews)
"Really convenient location, a beautiful view, comfortable amenities. Pleasant and helpful communication with host."
United States
April B.
The price is NZ$474
includes taxes & fees
11 Nov - 12 Nov
Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

20. Waikiki Skyline 28th Floor Hawaiian Monarch

Waikiki Skyline 28th Floor Hawaiian Monarch
Waikiki
9.8 out of 10, Exceptional, (6 reviews)
"Awesome place to stay in."
Canada
Zsarina
The price is NZ$518
includes taxes & fees
18 Nov - 19 Nov
Waikiki Skyline 28th Floor Hawaiian Monarch
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

Find out more about Kailua

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kailua holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kailua. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Kailua. Seeing all the best attractions is bound to make you fall in love with Kailua. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Kailua short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

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?

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY: This highly rated holiday home rental in Kailua is located on the beach, and has a balcony, a private garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Other favourite homes for rent in Kailua are BEST LICENSED LOCATION The VIEWHOUSE LANIKAI 1990NUC-1739 and Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa..

How many holiday rentals are there in Kailua?

With 139 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?

Kalama Beach Park and Kailua Bay 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 Walk 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.