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Holiday hires in Kailua

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

Kailua, United States
1 May — 2 May2
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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 November ($833). Conversely, the most expensive month to stay in Kailua is August ($3,829).

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

The cheapest day to stay in Kailua is Sunday ($476). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $2,828.
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Cheapest holiday rentals in Kailua, Hawaii

Discover affordable stays in Kailua that provide a quality experience without breaking the bank. Hotels in Kailua can be found for as low as $442 per night. There is currently one property in Kailua that can be booked for this price. Jenny's Cottage Waikiki is one of the hotels that can be booked for the lowest price in Kailua. Price data was last updated on 24 April 2025
These Kailua properties charge the lowest price per night of those we've come across. As prices can vary by date, change the dates if you're flexible to compare rates.
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Jenny's Cottage Waikiki
Jenny's Cottage Waikiki

Jenny's Cottage Waikiki

Honolulu, O'ahu, HI, United States
5.1 km from city centre
Air conditioning
$442
Avg. per night
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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 24 April 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 24 April 2025.

  • How much does a holiday rental in Kailua cost?

    $1,111 per night is how much a holiday rental in Kailua costs, on average. $236 per night was the cheapest price recently found by our users, though anything for $956 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 October.

  • 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 La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu) as it’s currently the most popular Bed & Breakfast rental among our users.

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