Historic Kailua Village holiday lettings
We found 992 holiday rentals — enter your dates for availability
Select from 42 houses, 87 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
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Historic Kailua Village
Find the best place to stay - Historic Kailua Village

🌴Ocean View Kona Retreat•Walk to Beach,Dining & Shops Pool•Free Parking•Sleeps 5
Sleeps 5 · 1 bedroom · 2 bathrooms

Hale Kona Kai by Casago Kona
Sleeps 4 · 1 bedroom · 1 bathroom

Summer Deal Ocean View 2BR Kona Condo with Lanai and Resort Pool
Sleeps 4 · 2 bedrooms · 2 bathrooms

Top floor, Ocean view! Very quiet 1 bed/2 bath.
Sleeps 2 · 1 bedroom · 2 bathrooms

Full ocean view from Kailua Village 602
Sleeps 2 · 1 bedroom · 1 bathroom

Kona Plaza#409: Top Floor, Downtown, Rare 3 bedroom Penthouse with Ocean View
Sleeps 8 · 3 bedrooms · 2 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore 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.
More holiday ideas
- Keiki Beach Holiday Rentals
- Kailua-Kona Holiday Rentals
- Kona Islander Inn Holiday Rentals
- Kona Brewing Company Holiday Rentals
- Old Kona Airport State Recreation Area Holiday Rentals
- Hulihee Palace Holiday Rentals
- Hulihe‘e Palace State Monument Holiday Rentals
- Honl's Beach Holiday Rentals
- Kbxtreme Holiday Rentals
- Kona Alii Holiday Rentals
- Kailua Bay Resort Holiday Rentals
- Kona Plaza Holiday Rentals
- Kona Hawaiian Village Holiday Rentals
- Kona Hawaiian Resort Holiday Rentals
- Kona Mansions Holiday Rentals
- Sea Village Holiday Rentals
- Kailua Village Holiday Rentals
- Hale Kona Kai Holiday Rentals
- Alii Cove Holiday Rentals
- Kona Shores Holiday Rentals
- Kalanikai Holiday Rentals
- Alii Park Place Holiday Rentals
- Kona Billfisher Holiday Rentals
- Swing Zone Holiday Rentals
- Kona Sea Ridge Holiday Rentals
- Kona Reef Holiday Rentals
- Kona Bay Estates Holiday Rentals
- Kamakahonu Beach Holiday Rentals
- Kona Pacific Holiday Rentals
- Kona Community Aquatic Center Holiday Rentals
- Cottages in Volcano
- Cabins in Volcano
- Apartments in Kailua-Kona
- Beach rentals in Kailua-Kona
- Cottages in Kailua-Kona
- Houses in Kailua-Kona
- Oceanfront rentals in Kailua-Kona
- Rentals with pool in Kailua-Kona
- Resorts in Kailua-Kona
- Villas in Kailua-Kona
- Longstay Hotels in Kailua-Kona
- Castles in Ahihi-Kinau Natural Area Reserve
- Longstay Hotels in Captain Cook
- Oceanfront rentals in Hana
- Longstay Hotels in Hana
- Beach rentals in Maui
- Houses in Honaunau-Napoopoo
- Cottages in Wailea
- Houses in Wailea
- Oceanfront rentals in Wailea
- Longstay Hotels in Wailea
- Oceanfront rentals near Mokapu Beach
- Villas in Kamaole Beach Park
- Apartments in Waikoloa Village
- Houses in Waikoloa Village
- Rv and caravan rentals in Kipahulu Visitor Center
- Rentals with pool near Kipahulu Visitor Center
- Apartments in Kona Coast
- Rentals with pool in Kona Coast
- Resorts in Kona Coast
- Cottages in Red Sand Beach
- Beach rentals in Kamuela
- Houses in Kamuela
- Bed and breakfasts in Haleakala National Park
- Bed and breakfasts in Kona Cloud Forest Sanctuary
- Houses in Pahoa
- Rv and caravan rentals in Puaʻa Kaʻa State Wayside Park
- Houseboats in Little Beach
- Longstay near Mauna Lani
- Bed and breakfasts in Hana Forest Reserve
- Castles in Ulua Beach
- Apartments in Hawaii Island
- Beach rentals in Hawaii Island
- Cottages in Hawaii Island
- Oceanfront rentals in Hawaii Island
- Rentals with pool in Hawaii Island
- Resorts in Hawaii Island
- Villas in Hawaii Island
- Cabins in Richardson's Ocean Park
- Longstay Hotels in Makena
- Apartments in Keaau
- Apartments in Hawaii
- Beach rentals in Hawaii
- Cottages in Hawaii
- Family rentals in Hawaii
- Houses in Hawaii
- Cabins in Hawaii
- Oceanfront rentals in Hawaii
- Rentals with pool in Hawaii
- Townhouses in Hawaii
- Villas in Hawaii
- Longstay Hotels in Hawaii
- Apartments in Hilo
- Houses in Hilo
- Oceanfront rentals in Hilo
- Longstay Hotels in Hilo
- Apartments in Puako
- Oceanfront rentals in Puako





