Historic Kailua Village vacation rentals

We found 873 vacation rentals — enter your dates for availability

Select from 40 houses, 78 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:Dec 5 - Dec 12

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

Pool
9.6 out of 10 rating
Exceptional
(97 reviews)

Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

Kailua-Kona, HI

11% off
Price is $1,141
$7,986 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

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 401 options available throughout the area. These condos are typically located close to the beach and various local attractions, offering travelers easy access to the vibrant atmosphere of Kailua. Most condos come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and balconies or patios that provide stunning views of the surroundings.

Apartments also see a good number of rentals, with around 68 available, often situated in quieter parts of the village, allowing visitors to enjoy a more relaxed atmosphere. Additionally, there are roughly 48 vacation houses, which are ideal for families or larger groups seeking more space. These homes generally feature multiple bedrooms, private outdoor areas, and amenities like BBQ grills, making them great for gatherings and enjoying the beautiful Hawaiian weather.
Are there any beach house rentals in Historic Kailua Village?
In Historic Kailua Village, Hawaii, there are approximately 958 beach house rentals available, offering travelers a wide range of options. These beach houses are typically located close to the picturesque Kailua Beach and Lanikai Beach, making them ideal for those looking to enjoy sun, sand, and surf.

Travelers can expect various amenities including spacious living areas, fully equipped kitchens for home-cooked meals, and outdoor patios or decks for relaxing and soaking up the tropical ambiance. Many properties also feature private pools, BBQ facilities, and easy access to local shops and restaurants, enhancing the overall vacation experience.
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 typically include fully equipped kitchens, which allow guests to prepare their own meals. Many properties offer access to shared pools, providing a refreshing spot to relax and socialize. Travelers can also expect amenities like coffee and tea makers and blenders, making morning routines and snack preparation convenient.
Are there any family house rentals in Historic Kailua Village?
In Historic Kailua Village, families will find a wealth of vacation rentals—approximately 285 options available for those seeking a memorable getaway. This charming area offers easy access to beautiful beaches, such as Kailua Beach and Lanikai Beach, which are great for swimming and sunbathing, making it ideal for families.

Many properties in the village feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios or balconies where you can enjoy the tropical breeze. Additionally, some rentals may include amenities like private pools, game rooms, and even beach gear to enhance your stay.

The locale is also close to various parks and recreational areas, providing opportunities for hiking, biking, and exploring the stunning natural surroundings.
Can I rent a vacation home with a pool or hot tub in Historic Kailua Village?
In Historic Kailua Village, travelers have an excellent selection of vacation homes available for rent that feature both pools and hot tubs, with around 452 properties offering pools and 173 providing hot tubs. This beautiful area is known for its stunning beaches and vibrant local culture, making it a desirable destination for relaxation and outdoor activities.

Many of these rentals come equipped with amenities such as private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for family gatherings or groups. Additionally, properties may include features like barbecue grills, comfortable lounge furniture, and direct access to nearby beaches, enhancing the overall vacation experience.
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.
Are there pet-friendly vacation rentals in Historic Kailua Village?
Yes, you can book pet-friendly vacation rentals in Historic Kailua Village, where there are several options available for travelers with pets. Many of the rentals in this area come equipped with convenient amenities such as fully equipped kitchens, outdoor spaces, and easy access to local attractions. Visitors can expect comfortable living arrangements that cater to both humans and their furry companions.

The neighborhood is well-situated near beautiful beaches and parks, making it a fantastic choice for pet owners who enjoy outdoor activities. Kailua Beach Park is a nearby highlight, offering ample space for dogs to run and play, as well as walking paths and picnic areas. Additionally, the charming local shops and cafes often welcome pets, enhancing the overall experience for those traveling with their four-legged friends.
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?
March is the most popular time to visit Historic Kailua Village, attracting travelers looking to soak in the vibrant culture and stunning natural beauty of Hawaii. This peak season, which spans from January to March, coincides with warm temperatures averaging in the mid-70s to low-80s Fahrenheit, creating ideal conditions for outdoor activities like hiking, snorkeling, and exploring local markets.

During these months, visitors can enjoy a variety of festivals and events that showcase the rich heritage of the area. The charming village atmosphere invites leisurely strolls along the waterfront, where you can take in breathtaking ocean views and discover unique shops and eateries.

For those seeking a more budget-friendly option, consider planning your visit in October. This month, while quieter, still offers pleasant weather and a chance to experience the local charm without the bustling crowds. You'll find opportunities to explore the beautiful beaches and lush landscapes at a more relaxed pace while enjoying lower rental rates.

Ultimately, the best time to visit Historic Kailua Village depends on your travel preferences—whether you crave the vibrant energy of the peak season or the tranquility of the off-peak months.
Are there any remote work vacation rentals in Historic Kailua Village?
In Historic Kailua Village, Hawaii, there is a substantial selection of remote work vacation rentals available, with around 474 options to choose from. This vibrant area, known for its beautiful beaches and rich history, offers properties that cater specifically to those looking to blend work and leisure. Many rentals feature dedicated office spaces, desks with ergonomic chairs, and reliable Wi-Fi, making it convenient for remote workers to stay productive while enjoying their surroundings.

Additionally, these rentals often include amenities such as full kitchens, outdoor patios, and sometimes even views of the ocean, allowing guests to relax and recharge after a day of work. Being located near the waterfront means that after hours, travelers can easily access local dining, shopping, and recreational activities like kayaking or snorkeling, adding an enjoyable balance to their work-life experience. 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?
In Historic Kailua Village, visitors can enjoy a range of attractions that highlight the area's rich cultural and natural beauty. The Kailua Pier is a central point, offering stunning views of the ocean, and serves as a launch point for various water activities such as snorkeling and kayaking. Nearby, the Mokuaikaua Church, the oldest Christian church in Hawaii, provides a glimpse into the region's historical significance.

The village is also close to Kailua Bay, superb for swimming and sunbathing, while the scenic Ali'i Drive features charming shops and local eateries, enhancing the overall experience. For those interested in history, the Hulihee Palace, a former royal vacation home, showcases Hawaiian artifacts and offers guided tours, making it a must-visit for history enthusiasts.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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