Historic Kailua Village holiday lettings

We found 871 holiday rentals — enter your dates for availability

Select from 39 houses, 80 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:6 Mar - 13 Mar

Image gallery for Experience historic charm near Kailua Pier

Turtle at Two Step.
9.6 out of 10, Exceptional, (209 reviews)
Exceptional
(209 reviews)

Experience historic charm near Kailua Pier

Kailua-Kona, HI

7% off
Price is £1,548
for 7 nights, 1 apartment
£221 per night
includes taxes & fees
Experience historic charm near Kailua Pier

Find spaces that suit your style

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  • 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

What is the most popular type of holiday rental in Historic Kailua Village?
In Historic Kailua Village, the most popular types of holiday rentals are condos, with approximately 421 available throughout the area. These condos are typically situated near the picturesque Kailua Beach and offer modern amenities such as fully equipped kitchens, spacious living areas, and often private balconies with stunning views of the ocean. Many also include access to communal pools and outdoor BBQ areas, making them ideal for both relaxation and socialising.
Are there any beach house rentals in Historic Kailua Village?
In Historic Kailua Village, Hawaii, there are approximately 900 beach house rentals available, making it a popular destination for those seeking a coastal getaway. These rentals often feature stunning ocean views, spacious living areas, and fully equipped kitchens, allowing guests to prepare their own meals while enjoying the tropical surroundings. Many properties include outdoor amenities such as private decks, BBQ grills, and easy access to the beach, great for families and groups looking to relax by the shore. Being situated close to points of interest like Kailua Beach Park and Lanikai Beach, visitors can easily explore the area's natural beauty and engage in activities such as swimming, kayaking, and hiking.
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?
March is the most popular month to visit Historic Kailua Village, attracting travellers eager to enjoy the beautiful beaches and vibrant local culture. The peak season runs from January to March, offering ideal conditions for outdoor activities such as snorkelling, kayaking, and hiking. With temperatures averaging around 25-28 degrees Celsius, it's superb for those who love to explore and soak up the sun.

During this bustling period, visitors can take part in the enchanting atmosphere of the village, with many opportunities to experience traditional Hawaiian festivities and local cuisine. The pleasant climate and warm ocean waters make it a fantastic time to engage in water sports or simply relax on the beach.

For those looking for a more budget-friendly option, October presents a wonderful opportunity to visit. The weather remains warm, and while it's a quieter month in terms of tourist activity, the natural beauty of the island is still on full display. You can take advantage of lower rental rates while enjoying peaceful walks along the beach and exploring the unique shops and eateries without the crowds.
Are there any remote work holiday rentals in Historic Kailua Village?
In Historic Kailua Village, there are numerous remote work holiday rentals available, with around 526 options to choose from. This vibrant area is renowned for its stunning beaches and rich cultural heritage, making it an appealing destination for those looking to blend work and leisure. Many properties in this locale come equipped with modern amenities tailored for remote work, including high-speed Wi-Fi, dedicated workspaces with desks and ergonomic chairs, and even computer monitors in some cases. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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?
In Historic Kailua Village, visitors can immerse themselves in a rich tapestry of attractions. The picturesque Kailua Bay offers opportunities for swimming, kayaking, and paddleboarding, making it a prime spot for water activities. Along the waterfront, holiday rentals can provide stunning ocean views and easy access to the beach.

The village is also home to the historic Kailua Pier, a charming area where one can enjoy local shops and eateries. Nearby, the expansive Kaloko-Honokōhau National Historical Park presents a glimpse into Hawaiian history and culture, featuring petroglyphs and ancient fishponds.
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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