Photo by Joe Ratliffe

Historic Kailua Village holiday lettings

We found 890 holiday rentals — enter your dates for availability

Select from 43 houses, 82 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.

Holiday rentals with weekly discounts - Historic Kailua Village

Showing deals for:29 May - 5 Jun

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    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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Historic Kailua Village?
Prices for holiday rentals in Historic Kailua Village vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Historic Kailua Village to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Historic Kailua Village holiday house rentals?
You can find great discounts on house rentals in Historic Kailua Village on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Historic Kailua Village holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Historic Kailua Village with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Historic Kailua Village?
A long-stay holiday rental in Historic Kailua Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Historic Kailua Village for a holiday rental?
The best time to visit Historic Kailua Village is during the peak season from January to March, with March being particularly popular among travellers seeking a sun-soaked escape. This vibrant period attracts visitors keen on enjoying the beautiful beaches, water sports, and the rich cultural experiences that Kailua Village offers.

During these months, you can expect warm temperatures averaging around 23 to 29 degrees Celsius, superb for outdoor activities such as kayaking, snorkelling, and hiking in the nearby lush landscapes. The comfortable climate allows for leisurely strolls along the beach and engaging in local festivities that showcase Hawaiian culture.

For those looking for a more budget-friendly option, October is a fantastic time to visit. This month often sees fewer crowds, allowing for a more tranquil experience while still enjoying pleasant weather. It's a lovely time to explore the area's natural beauty and indulge in local cuisine without the hustle and bustle of peak season.
How early should I book a Historic Kailua Village holiday rental?
Book your Historic Kailua Village holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Historic Kailua Village, Hawaii, United States of America?
In Historic Kailua Village, visitors can immerse themselves in the rich cultural heritage and natural beauty of Hawaii. The area is renowned for its stunning beaches, with Kailua Beach Park being a standout destination, offering soft sands and clear waters great for swimming and sunbathing.

Nearby, the Mokuaikaua Church, the oldest Christian church in Hawaii, showcases beautiful architecture and provides insight into the region's history. The Kailua Pier is another focal point, ideal for ocean activities such as kayaking and paddleboarding while also serving as a great spot for watching sunsets.

The village is also home to various shops, art galleries, and restaurants that reflect local flavours and craftsmanship.
Can I change or cancel my Historic Kailua Village home rental booking on Vrbo?
To find Historic Kailua Village holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Historic Kailua Village holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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