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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Kailua holiday rentals

Lobby

Comfy and Modern Condo By Waikiki

Comfy and Modern Condo By Waikiki
3.5 star property
Waikiki
The price is S$483
includes taxes & fees
23 Jun - 24 Jun
Comfy and Modern Condo By Waikiki
Mountain view

Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre
4.0 star property
Downtown Honolulu
7.6 out of 10, Good, (131 reviews)
"Lovely staff!! Nice set up!! Beautiful views!"
United States
Karley
The price is S$289
includes taxes & fees
29 Jun - 30 Jun
Bishop Suites At The Executive Centre
Beach

@ Marbella Lane -coastal Retreat Near Diamond Head

@ Marbella Lane -coastal Retreat Near Diamond Head
2.5 star property
Diamond Head - Kapahulu - St. Louis
The price is S$719
includes taxes & fees
13 Jul - 14 Jul
@ Marbella Lane -coastal Retreat Near Diamond Head
Living area

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very good, (44 reviews)
"Had a great stay, the room had everything we needed and more, great location close to everything, for sure coming back again with my whole family:)"
United States
Laura
The price is S$470
includes taxes & fees
24 Jun - 25 Jun
Ilikai Marina Vacations
Living area

Island Colony hotel

Island Colony hotel
2.5 star property
Waikiki
10.0 out of 10, Exceptional, (1 review)
"The only down side is the parking structure as I paid for 5 days but could not park in it on 1 of the nights."
United States
Jesus
The price is S$362
includes taxes & fees
23 Jun - 24 Jun
Island Colony hotel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kailua Hotel Reviews

Halepuna Waikiki by Halekulani

Halepuna Waikiki by Halekulani

10/10 Excellent
"I love the property was private but still in the middle of Waikiki. Staff were great. And accommodating. I just wish my family could have been all in the same floor. House keeping was thoughtful and very helpful. They wrote thank you notes for us. . Bell staff were very welcoming especially RJ. He was very genuine , funny and exuded the aloha spirit. We had three rooms for our family and he made sure all of us felt welcomed every single time we walked in the hotel. When we left he personally took care of all our luggage’s and weighed it. He took off all the worries. Thank you RJ! Everyone should follow suit!"
JEAN 14-night trip
Posted 6 hours ago
Halepuna Waikiki by Halekulani

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.

How many holiday rentals are there in Kailua?

With 142 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?

Lanikai Beach 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 Waikiki Beach and Ala Moana Center 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.