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Historic Kailua Village vacation rentals

We found 891 vacation rentals — enter your dates for availability

Select from 43 houses, 82 apartments, and other vacation rentals to find the perfect place for your stay in Historic Kailua Village. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you need and want for your stay, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Historic Kailua Village

Showing deals for:May 22 - May 29

Image gallery for Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

Pool
9.4 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)

Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

Kailua-Kona

11% off
Price is $1,060
$7,419 for 7 nights
All fees included
Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

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Find out more about Historic Kailua Village

Why visit Historic Kailua Village

  • Beautiful Beaches: Enjoy stunning beaches with clear waters, perfect for swimming and sunbathing.
  • Kailua Pier: Visit the iconic Kailua Pier, a hub for fishing, boating, and scenic views.
  • Cultural Experiences: Immerse yourself in local history and culture through charming shops and eateries.
  • Outdoor Adventures: Engage in various outdoor activities like snorkeling, kayaking, and hiking.
  • Diverse Accommodations: Choose from cozy cottages, spacious homes, and luxurious villas for a comfortable stay.

Popular types of accommodation around Historic Kailua Village

Planning a getaway to Historic Kailua Village? Discover the charm of this picturesque destination by choosing from a variety of accommodations. Popular options include cozy kona cottages, spacious houses, and luxurious kona villas. Whether you prefer a modern suite or the inviting star condo, you'll find ample parking for your convenience. Start your adventure today by exploring the best vacation rentals in Kailua.

  • Condos: A favored choice among travelers, these stylish units offer comfort and convenience right in the heart of Historic Kailua Village.
  • Houses: Ideal for families or groups, these spacious homes provide a homely atmosphere and plenty of privacy.
  • Villas: Luxurious and often equipped with stunning views, villas provide a high-end experience for those seeking relaxation.
  • Apartments: A practical option, apartments offer a cozy stay with essential amenities for a hassle-free vacation.
  • Cottages: Quaint and charming, cottages are perfect for a romantic getaway or a peaceful retreat.**

Top attractions in and around Historic Kailua Village

Historic Kailua Village in Kailua-Kona, Hawaii, offers a perfect blend of outdoor adventure and scenic beauty. Visitors can explore beautiful beaches, the iconic Kailua Pier, and the rich plantation history. This vibrant area is ideal for those seeking cultural experiences and outdoor activities. Don't miss the charm of Kailua Village and the various fun activities available, making it a must-visit destination for your Hawaiian vacation.

  • Kailua Pier: A vibrant jetty located in Historic Kailua Village, Kailua Pier offers a tropical ambiance perfect for leisurely strolls and watching boats come in and out. It's a great starting point for excursions and water activities.
  • Magic Sands Beach: Located 3 miles from Historic Kailua Village, this beautiful beach is known for its soft sands and stunning sunsets. It's an ideal spot for sunbathing, swimming, and enjoying beach vibes.
  • Kaloko-Honokohau National Historical Park: Just 4 miles away, this park showcases rich Hawaiian culture and history, with ancient fishponds, petroglyphs, and scenic trails, providing a unique insight into the island's past.

Things to do recommended for couples

For a romantic getaway in Historic Kailua Village, savor a delightful meal at KBXtreme, known for its vibrant ambiance. Don't miss the Haleo Luau, just 6 miles away, offering a unique dining experience that blends culture and romance. Perfect for couples seeking memorable moments.

Things to do recommended for families

Families visiting Historic Kailua Village can splash around at the Kona Community Aquatic Center, which offers a fun atmosphere for all ages. For a sweet treat, head to Donkey Balls Factory and Store, located 9 miles away, where kids can indulge in delicious chocolates and enjoy a family-friendly vibe.

Things to do recommended for groups

Experience the local flavors at Kona Brewing Company for a fun evening, shop at Kona Inn Shopping Village for unique finds, or enjoy a round of golf at Big Island Country Club, just 3 miles away, perfect for group bonding in the beautiful outdoors.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Historic Kailua Village

When traveling with a group, family, or pets, or if you're planning an extended stay, it’s important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Historic Kailua Village with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Historic Kailua Village with young kids: Traveling with little ones can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Historic Kailua Village: For many families, a trip wouldn’t feel complete without their beloved pet joining in on the fun. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that your furry friend feels just as comfortable as you do.
  • Planning for a long term stay visiting Historic Kailua Village: If you're seeking vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Historic Kailua Village

Explore the enchanting Historic Kailua Village in Kailua-Kona, Hawaii, where tropical vibes meet family-friendly charm. Stroll through downtown Kailua, rich in history and local culture, offering a unique blend of adventure and scenic beauty. Enjoy outdoor activities, visit quaint shops, and savor delicious Hawaiian cuisine as you immerse yourself in the vibrant atmosphere of this captivating neighborhood. Your vacation in Kailua-Kona promises unforgettable experiences in this delightful coastal community.

  • Kailua-Kona: Nestled along the western coast of the Big Island, Kailua-Kona is a vibrant city rich in history and culture. Historic Kailua Village serves as the heart of this destination, offering visitors a delightful blend of outdoor adventures and scenic beauty. From world-class golf courses to serene campgrounds, there’s something for everyone. The area boasts stunning beaches perfect for swimming, sunbathing, and snorkeling, along with the nearby Kaloko-Honokohau National Historical Park, which showcases the region's natural beauty and cultural heritage. Enjoy the local shops, restaurants, and the famous Kona coffee as you soak in the island's laid-back atmosphere.
  • Holualoa Village: Located approximately 3 miles from Historic Kailua Village, Holualoa Village is a charming neighborhood known for its artistic vibe and lush landscapes. This hillside community is surrounded by coffee farms and offers breathtaking views of the coastline. Visitors can enjoy outdoor adventures like hiking and exploring the scenic beauty of the area, along with the opportunity to visit local art galleries and craft shops. The nearby beaches and campgrounds provide perfect spots for relaxation and family outings. Holualoa Village embodies the essence of Hawaiian culture and is a must-visit for those seeking a unique experience.
  • Honokohau: Situated 2 miles away from Historic Kailua Village, Honokohau is a quaint village that invites travelers to explore its beautiful natural surroundings. Known for its outdoor activities, visitors can enjoy the local beaches and mountain areas ideal for hiking and relaxation. The area features several golf courses, making it a golfer's paradise. With ample campground options, Honokohau is perfect for families and adventurers alike. Take a moment to immerse yourself in the local culture and enjoy the stunning scenery that this hidden gem has to offer.

Best time to go to Historic Kailua Village

If you're planning a trip to Historic Kailua Village, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like May and September to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January71.6°F (22.0°C)Light RainMostly SunnySlightly HighAverage
February71.2°F (21.8°C)Light RainMostly SunnySlightly HighAverage
March71.8°F (22.1°C)Light RainMostly SunnySlightly HighAverage
April72.5°F (22.5°C)Moderate RainMostly CloudyAverageAverage
May73.6°F (23.1°C)Moderate RainMostly CloudySlightly LowSlightly Low
June74.5°F (23.6°C)Moderate RainMostly CloudyAverageSlightly High
July75.7°F (24.3°C)Moderate RainMostly CloudyAverageSlightly High
August76.3°F (24.6°C)Moderate RainMostly CloudyAverageAverage
September76.1°F (24.5°C)Moderate RainMostly CloudySlightly LowSlightly Low
October76.1°F (24.5°C)Light RainMostly SunnySlightly LowSlightly Low
November74.5°F (23.6°C)Light RainMostly SunnyAverageAverage
December72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Also, extending your stay can often lead to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer has its perks. Become a member of our One Key rewards program to unlock exclusive savings and accumulate OneKeyCash on eligible stays. Sign up now and begin earning rewards.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your trips, pick up where you left off, and manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Historic Kailua Village?
In Historic Kailua Village, condos are the most popular type of vacation rental, with about 436 available across the area. These condos are often located close to the beach and local attractions, providing easy access to beautiful views and vibrant dining options. Most units feature modern amenities, including fully equipped kitchens, spacious living areas, and private balconies to enjoy the tropical atmosphere.

Apartments also make a significant presence, with approximately 66 units spread throughout the village. These accommodations typically offer a cozy and convenient stay, complete with kitchen facilities and comfortable living spaces. For those seeking more space, around 37 vacation houses are available, ideal for families or groups. These homes generally include multiple bedrooms, outdoor areas for relaxation, and often a grill for outdoor cooking.
Are there any beach house rentals in Historic Kailua Village?
In Historic Kailua Village, there are approximately 948 beach house vacation rentals available, making it a popular destination for travelers. These rentals are typically situated in charming neighborhoods close to Kailua Beach Park and the picturesque coastline. Visitors can expect a variety of amenities, including fully equipped kitchens, spacious living areas, and outdoor patios or decks that often provide stunning views of the ocean or lush landscapes. Many properties also feature BBQ grills and easy access to nearby water activities, making them ideal for families and groups looking to enjoy the beach lifestyle.
How much does it cost to rent a vacation home in Historic Kailua Village?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Historic Kailua Village?
In Historic Kailua Village, popular rental amenities include fully equipped kitchens, making it easy for travelers to prepare meals during their stay. Many properties also offer onsite parking, which is a convenient feature for those renting a car to explore the island. Guests can enjoy their morning coffee or tea with coffee and tea makers available in the rentals. Balconies are common, providing a lovely spot to relax and take in the views. Additionally, many rentals feature shared pools, allowing guests to cool off and socialize in a refreshing environment.
Can I find family house rentals in Historic Kailua Village?
In Historic Kailua Village, there are numerous family-friendly house rentals available, totaling around 311 options. This charming area offers a vibrant blend of beachside beauty and local culture, making it an excellent choice for families. Many homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces superb for relaxation or play.

Visitors can enjoy amenities such as private pools, outdoor dining areas, and easy access to beautiful beaches like Kailua Beach and Lanikai Beach, which are ideal for swimming and sunbathing. Additionally, the neighborhood is close to local attractions, including the Kailua Farmers Market, where families can explore fresh produce and artisan goods.
Can I rent a vacation home with a pool or hot tub in Historic Kailua Village?
In Historic Kailua Village, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with approximately 497 options for properties with pools and 171 with hot tubs. This charming area in Hawaii offers a picturesque setting with close proximity to beautiful beaches and local attractions.

Many of these rentals come equipped with desirable amenities such as private pools, relaxing hot tubs, outdoor dining areas, and fully stocked kitchens, making them superb for families or groups looking to unwind.
Are there any Historic Kailua Village vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Historic Kailua Village with parking available—perfect for families or travelers 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 book pet-friendly vacation rentals in Historic Kailua Village?
Yes, you can book pet-friendly vacation rentals in Historic Kailua Village, with about 16 options available. This charming area offers a range of vacation rentals that typically include amenities such as spacious living areas, well-equipped kitchens, and outdoor spaces superb for relaxing after a day of exploring. Many properties may also feature private lanai, air conditioning, and easy access to the beach.

Being in Historic Kailua Village, you'll find yourself close to beautiful beaches like Kailua Beach and Lanikai Beach, both of which are known for their stunning views and opportunities for water activities. The surroundings also offer pet-friendly parks and scenic walking paths, making it convenient for travelers with pets to enjoy the outdoors.
Can I find long-stay vacation rentals in Historic Kailua Village?
A long-stay vacation rental in Historic Kailua Village is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Historic Kailua Village for a vacation rental?
The most popular time to visit Historic Kailua Village is from January to March, with March being particularly favored by travelers seeking a tropical getaway. During these months, the area comes alive with vibrant festivities, warm temperatures in the high 70s to mid-80s Fahrenheit, and a plethora of outdoor activities. Visitors can experience firsthand the local culture, enjoy breathtaking beach days, and explore the scenic beauty of the Big Island.

March is particularly appealing due to its comfortable climate, superb for beachgoers and adventure seekers alike. You can indulge in kayaking, snorkeling, or simply lounging on the pristine shores, all while surrounded by the stunning vistas of the Pacific Ocean. The gentle trade winds provide a pleasant breeze, enhancing your outdoor experiences.

For those looking for a more budget-friendly option, consider visiting in October. This month typically sees fewer tourists, allowing you to enjoy a more tranquil atmosphere. It's an excellent time for exploring the area's rich history, including visits to cultural sites and local markets without the hustle and bustle of peak season.

Ultimately, the best time to book a vacation rental in Historic Kailua Village hinges on your preference for lively events and warm weather in peak season or the peaceful charm of the shoulder months.
Are there any remote work vacation rentals in Historic Kailua Village?
In Historic Kailua Village, Hawaii, there are numerous options for remote work vacation rentals, with around 527 available to choose from. Many of these properties are equipped with essential amenities for remote work, such as free Wi-Fi, desks, and comfortable chairs, ensuring a productive environment. Travelers can expect to find a variety of accommodations, from cozy studios to spacious multi-bedroom homes, many of which feature modern kitchens and outdoor spaces where one can relax after a day of work.

The village itself is a vibrant area with beautiful beaches, local shops, and restaurants, providing a superb balance of work and leisure. Additionally, the stunning scenery and warm climate make it an ideal location for those looking to blend work with a bit of paradise. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic Kailua Village vacation rental?
Book your Historic Kailua Village vacation 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 vacation 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 take part in a rich blend of natural beauty and cultural experiences. A must-see is Kailua Beach Park, renowned for its soft white sands and crystal-clear waters, superb for swimming, kayaking, and paddleboarding. The nearby Kaloko-Honokōhau National Historical Park offers insight into ancient Hawaiian culture, featuring well-preserved fishponds and petroglyphs.

The village itself is filled with charming shops and local eateries, where travelers can taste fresh seafood and traditional Hawaiian dishes. The Mokuaikaua Church, the oldest Christian church in Hawaii, is a key historical site, showcasing beautiful architecture and offering a glimpse into the region's past.

For those interested in marine life, the nearby Kailua Pier serves as a hub for boat tours and snorkeling excursions to explore the vibrant underwater ecosystems of the area.
Can I change or cancel my Historic Kailua Village home rental booking on Vrbo?
To find Historic Kailua Village vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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