Insights
Where to stay

Holiday hires in Kailua

Search and compare Kailua, HI holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

Travel insights for holiday rentals in Kailua

Use these up-to-date, data-driven insights about booking a holiday rental in Kailua including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Kailua?

The cheapest month to book a vacation rental in Kailua is March ($633). Conversely, the most expensive month to stay in Kailua is September ($2,170).

What is the cheapest day to stay in a vacation rental in Kailua?

The cheapest day to stay in Kailua is Saturday ($398). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $1,087.
Find deals

Where to stay in Kailua

Explore different neighbourhoods and areas within Kailua to find the perfect location for your stay. Map data was last updated on 9 December 2025.
Utilise the map to find properties close to the Kailua area(s) or attractions you plan on visiting. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday rental.

Facts about staying in Kailua

Find useful tips and insights about staying in Kailua to help you make the most of your experience. FAQs were last updated on 9 December 2025.

  • How much does a holiday rental in Kailua cost?

    $1,061 per night is how much a holiday rental in Kailua costs, on average. $269 per night was the cheapest price recently found by our users, though anything for $985 per night or less is a good deal. Keep in mind that Kailua holiday rental prices fluctuate throughout the year: the most expensive month to book is September, and the cheapest time to book is June.

  • Are there any Bed & Breakfast holiday rentals in Kailua?

    If you’re looking to book a Bed & Breakfast holiday rental in Kailua, then you have 24 to choose from. We recommend looking at Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast as it’s currently the most popular Bed & Breakfast rental among our users.

Find better results for your stay in Kailua