Downtown Kailua holiday homes

We found 90 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Downtown Kailua that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the amenities that you need and want, such as parking and air conditioning. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Can I find holiday rentals in Downtown Kailua?
Yes, there are holiday rentals close to the most popular sights in Downtown Kailua, or you can select a more secluded option if you're looking for a relaxing stay.
What's there to see and do in Downtown Kailua?
Explore the area and family-friendly sights such as Bishop Museum, or get out into nature at a spot like Waikiki Beach. Other popular places to visit in the area include Ala Moana Center and International Market Place.
What's a holiday rental in Downtown Kailua like?
Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Downtown Kailua. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.