Photo by Joe Ratliffe

Historic Kailua Village holiday rentals

We found 875 holiday rentals — enter your dates for availability

Select from 40 houses, 85 apartments and other holiday rentals to find the perfect place for your stay in Historic Kailua Village. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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

What is the most popular type of holiday home accommodation in Historic Kailua Village?
According to our research, condos are the most in-demand holiday property type in Historic Kailua Village. But having said that, everyone's idea of an awesome trip isn't the same. Stayz has holiday homes of all shapes, sizes and budgets, and we'll help you locate your ideal match.
How much does it cost to rent a holiday home in Historic Kailua Village?
A range of things affect how much you'll pay for a holiday home in Historic Kailua Village, such as the length of stay, type of property and season. However, all Stayz homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Historic Kailua Village?
The average price for a holiday home close to the beach in Historic Kailua Village depends on when you're visiting the area and the size and type of property you're searching for. Find prices quickly and easily on Stayz by entering your dates of travel. Then use the filters to choose the number of bedrooms and amenities that you need, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Historic Kailua Village?
Yes, there are. You can pick from 304 holiday homes that welcome pets in Historic Kailua Village on Stayz. Our furry friends need a getaway too, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Rover can get in on the family fun.
Can I rent a house with a pool in Historic Kailua Village?
Tick the "pool" box in our filter tool and you can choose from 278 houses with private pools in Historic Kailua Village on Stayz. Lazy soak or ball games and races? Leisure activities are up to you when your Stayz holiday property comes with a swimming pool.
What are popular home amenities in Historic Kailua Village?
When it comes to home amenities that people look for in Historic Kailua Village, a garden, a beach view and a fireplace rank the highest. With Stayz holiday homes, you'll enjoy choices to match your taste and style, whether you're planning to get away with family, friends or even pets.
Are there large group holiday homes in Historic Kailua Village?
With three properties that can host 10 people or more in Historic Kailua Village, you won't have to hold back on your invites. From fun family holidays to special events like weddings and birthday parties, Stayz can help you find a large group home that fits the occasion.
Are there holiday homes in Historic Kailua Village that welcome kids?
Gather your entire family for a fun-filled adventure in Historic Kailua Village at one of our 299 family-friendly holiday properties. A lot of these stays come with conveniences that are perfect for trips with youngsters, like laundry facilities, extra bedrooms and entertainment units. Just check the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Historic Kailua Village?
There are tons of fabulous things to do and see with the family in Historic Kailua Village, such as:

  • Kailua Pier
  • Magic Sands Beach
  • Kahaluu Beach Park

Are there one-bedroom holiday homes in Historic Kailua Village?
Yes, Historic Kailua Village has 185 one-bedroom homes on offer. Often situated in popular areas because of their smaller size, a one-bedroom home is ideal if you're getting away with a pal or your partner. And with plenty of home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back while discovering this incredible destination.
Can I find two-bedroom holiday homes in Historic Kailua Village?
Gather your besties and experience complete comfort and privacy in one of the 68 two-bedroom holiday properties Historic Kailua Village has to offer.
Are there holiday homes with WiFi in Historic Kailua Village?
Historic Kailua Village has 131 holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Historic Kailua Village?
You'll have your pick of 267 Stayz holiday homes with air conditioning in Historic Kailua Village giving you that gentle, cool breeze and extra element of comfort. Just enter your dates of travel and then use our filters to look for stays with air conditioning.
How old do you have to be to rent a holiday home in Historic Kailua Village?
The minimum age is normally 16, 18 or 21. It can differ between properties on Stayz, so check the rules of your preferred Historic Kailua Village holiday home before booking your escape.
How long can I rent a holiday home in Historic Kailua Village for?
The amount of time you can stay in a Historic Kailua Village holiday home for depends on each property. Simply put in your preferred travel dates to browse options that offer long-term stays. They have everything you need to make your extended trip more comfortable and enjoyable, like laundries and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

More holiday ideas