Historic Kailua Village vacation rentals

We found 823 vacation rentals — enter your dates for availability

Select from 37 houses, 81 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:Aug 29 - Sep 5
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Find out more about Historic Kailua Village

Find out more about Historic Kailua Village

Why visit Historic Kailua Village

  1. Stunning Beaches: Enjoy the beautiful sandy shores and clear waters ideal for swimming and sunbathing.
  2. Cultural Experiences: Discover local history at attractions like the Sea Village and enjoy views of Kilauea.
  3. Vibrant Kailua Pier: Stroll along the lively pier, perfect for sightseeing and socializing.
  4. Charming Downtown Kailua: Explore shops, restaurants, and the rich history that defines this enchanting village.
  5. Diverse Accommodations: Choose from cozy condos to spacious homes, ensuring a perfect stay for every traveler.

Popular types of accommodation around Historic Kailua Village

Historic Kailua Village offers a variety of vacation rentals to suit every traveler’s needs. Whether you're looking for cozy condos, spacious houses, or modern apartments, you’ll find the perfect spot to unwind. Popular options include Kailua Village condos and Kona vacation condos, each featuring delightful amenities and stunning views. Choose from our selection of condo rentals in Kailua to create an unforgettable getaway.

  • Condos: The top choice for vacation rentals in Historic Kailua Village, offering modern amenities and great views.
  • Houses: A popular option for families and groups, providing space and privacy during your stay.
  • Apartments: A convenient choice for solo travelers or couples, featuring essential comforts in a compact layout.
  • Villas: Luxurious accommodations with upscale features, perfect for a relaxing getaway.
  • Cottages: Charming and cozy, these rentals offer a quaint retreat for a peaceful vacation experience.**

Top attractions in and around Historic Kailua Village

Historic Kailua Village in Kailua-Kona, Hawaii, offers a perfect getaway for outdoor and adventure enthusiasts. Visitors can enjoy stunning beaches, explore the vibrant Kailua Pier, and relax at Kailua Park. Cultural experiences abound, with attractions like the Sea Village and views of Kilauea, making it an ideal destination for those seeking scenic beauty and local charm.

  1. Kailua Pier: This picturesque jetty in Historic Kailua Village offers a vibrant atmosphere, perfect for embarking on tropical excursions, such as snorkeling and whale watching. Enjoy stunning ocean views and watch local fishermen at work.
  2. Magic Sands Beach: Located 3 miles from Historic Kailua Village, this beautiful beach is famous for its soft, golden sands and excellent swimming conditions. It’s a great spot for sunbathing, beach games, and enjoying breathtaking sunsets.
  3. Kaloko-Honokohau National Historical Park: Just 4 miles away, this park showcases rich Hawaiian culture and history, featuring ancient fishponds, petroglyphs, and stunning coastal trails, making it a serene place to explore nature and heritage.

Things to do recommended for couples

For a romantic getaway in Historic Kailua Village, savor a meal at KBXtreme, known for its lively atmosphere. Alternatively, indulge in a delightful experience at Haleo Luau, located 6 miles away, where you can enjoy authentic Hawaiian culture and cuisine under the stars.

Things to do recommended for families

Your family will love splashing around at the Kona Community Aquatic Center, a fun spot located in Historic Kailua Village. For a sweet treat, visit the Donkey Balls Factory and Store, just 9 miles away, where everyone can indulge in delicious chocolate-covered snacks.

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

If you're traveling with a group, with family, bringing pets, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Historic Kailua Village with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for socializing. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Historic Kailua Village with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Historic Kailua Village: For many families, a vacation isn't truly enjoyable without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Historic Kailua Village: If you're in search of vacation rentals that offer great deals 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Historic Kailua Village

Explore the enchanting Historic Kailua Village, where tropical vibes meet adventure! Stroll through charming downtown Kailua, discover the rich history of Historic Kailua, and enjoy the vibrant atmosphere of Big Island Kailua Village. Don’t miss the picturesque sights of downtown Kona, perfect for family-friendly outings and outdoor fun. With its scenic beauty and lively ambiance, Historic Kailua Village offers an unforgettable Hawaiian escape for every traveler.

  • Honokohau: Located a mere 2 miles from Historic Kailua Village, Honokohau is a charming village that beckons outdoor enthusiasts and adventure seekers. The area is renowned for its stunning scenery, with picturesque beaches and majestic mountains nearby. Visitors can enjoy a variety of activities, including rounds of golf at local courses or camping under the stars. The family-friendly beaches provide a perfect spot for relaxation and fun, making Honokohau an ideal destination for those looking to experience the great outdoors while soaking in the natural beauty of Hawaii.
  • Kahaluu Bay: Situated 4 miles away from Historic Kailua Village, Kahaluu Bay is a vibrant neighborhood famous for its underwater sports and beach activities. This area is a paradise for snorkelers and divers, thanks to its crystal-clear waters teeming with marine life. In addition to adventure activities, visitors can enjoy relaxing at the beach or spending time in the nearby park. With its breathtaking coastal views and engaging atmosphere, Kahaluu Bay is a must-visit for anyone looking to immerse themselves in Hawaii's natural wonders.
  • Keauhou: Just 5 miles from Historic Kailua Village, Keauhou is a quaint village that offers a perfect blend of outdoor adventure and serene scenery. Known for its stunning beaches and proximity to a national state park, visitors can explore hiking trails or enjoy a round of golf at the local country club. The area is ideal for families and nature lovers alike, providing ample opportunities for relaxation and exploration. Keauhou's inviting atmosphere and lush surroundings make it an excellent choice for those seeking a peaceful escape in paradise.

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 August to September tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 CloudySlightly LowAverage
September76.1°F (24.5°C)Moderate RainMostly CloudySlightly LowSlightly Low
October76.1°F (24.5°C)Light RainMostly SunnyAverageSlightly 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 vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash™ on the total booking amount. It certainly pays off to be the organizer! Enroll in our OneKey rewards program to unlock exclusive savings for members and earn OneKeyCash™ on eligible stays. Sign up today and begin reaping the rewards!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or organize your travel plans. You’ll find your saved or booked properties neatly categorized as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the waterfront beauty of Historic Kailua Village

The island views and other outdoor surroundings create an inviting atmosphere in Historic Kailua Village. Travelers to this walkable city praise the snorkeling, shopping and restaurants. If you're looking for accommodations with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Historic Kailua Village

Are you hoping to find top things to see and do in the city? You'll be sure to enjoy Historic Kailua Village for its snorkeling and jogging trails. Venture out of your vacation home and check out everything that makes Historic Kailua Village a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Kona Country Club (5.8 mi / 9.3 km)
  • Four Seasons Resort Hualalai Golf Course (12.9 mi / 20.8 km)
  • Makani Golf Club (15.7 mi / 25.3 km)
  • Kona Community Aquatic Center (0.7 mi / 1.1 km)
  • Mauka Meadows Coffee Farm (2.5 mi / 4 km)
  • Hula Daddy Kona Coffee Plantation (3.1 mi / 5 km)

Exploring the beaches and other natural features in Historic Kailua Village

Historic Kailua Village is famous for its island views, breathtaking sunsets and tropical locale. Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Historic Kailua Village. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Kamakahonu Beach (0.4 mi / 0.6 km)
  • Old Kona Airport State Recreation Area (0.7 mi / 1.1 km)
  • Magic Sands Beach (3.4 mi / 5.5 km)
  • Kaloko-Honokohau National Historical Park (3.7 mi / 5.9 km)
  • Kahalu'u Beach Park (4.5 mi / 7.2 km)
  • Keauhou Bay Beach (5.7 mi / 9.2 km)

Seasonal weather averages in Historic Kailua Village

Travelers speak highly of Historic Kailua Village for its snorkeling. If you're planning a vacation around the weather, August, September, October and July are the hottest months to visit, when temperatures average 76°F.

How to get to and around Historic Kailua Village

The nearest airport is in Kona Intl. Airport (KOA), located 7.4 mi (11.8 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Historic Kailua Village?
The most popular types of vacation rentals in Historic Kailua Village are condos. Ready for more choices? Vrbo has many options to match our guests’ requirements, so you’ll see vacation properties in all sizes, and for all budgets. The ideal fit is waiting for you — grab yours today.
How much does it cost to rent a vacation rental in Historic Kailua Village?
The average price for a vacation rental in Historic Kailua Village is determined by a number of factors, such as property type, season and length of stay. Whether you’re dreaming about a sprawling villa with room to move around or a comfy cabin just for the two of you, just add your travel dates to see stays with great value.
How much does it cost to rent a beach house in Historic Kailua Village?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Enter your Historic Kailua Village travel dates to see your options on Vrbo. Did someone just say “private pool”? Use our filters to select the amenities and features you want in your vacation home.
Are there pet-friendly vacation rentals in Historic Kailua Village?
Pack a bone and a squeezy toy for your pooch because Historic Kailua Village has 298 stays that roll out the welcome mat to pets. Let your furriest pal get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Historic Kailua Village?
Dig out your swimsuit and inflatable flamingo, because there are 274 houses with a private pool in Historic Kailua Village. Stay at one of these popular vacation homes and every day can be a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place to make a splash!
What are popular rental amenities in Historic Kailua Village?
When it comes to rental amenities that guests look for in Historic Kailua Village, a beach view, a chef and an electric car charging station rank highest. With Vrbo vacation rentals, you’ll find options to fit your style and taste, whether you’re going on a vacation with your partner, family members or even pets.
Are there large group vacation rentals in Historic Kailua Village?
With six vacation rentals that can sleep 10 or more people in Historic Kailua Village, there’s no need to cross anyone off the invite list. From family vacations to special events like Christmas or New Year’s Eve parties, Vrbo can help you find a large group rental to suit the occasion.
Are there vacation rentals in Historic Kailua Village that welcome kids?
With 293 family-friendly vacation rentals to choose from in Historic Kailua Village, now is an awesome time to introduce the kiddos to the wonders of travel. Just check our “Properties good for families” filter box to search for stays that come with conveniences perfect for traveling families, like living rooms, yards, bunk beds and hot tubs.
What are the top attractions for families in Historic Kailua Village?
Keep the kids occupied at these top family-friendly attractions in Historic Kailua Village:

  • Old Kona Airport State Recreation Area
  • Kona Community Aquatic Center
  • Hulihee Palace

Are there one-bedroom vacation rentals in Historic Kailua Village?
Yes, Historic Kailua Village has 181 one-bedroom rentals on offer. Often located in prime areas thanks to their compact size, a one-bedroom rental is perfect if you’re traveling with a pal or your partner. And with home comforts such as kitchens and more privacy than a standard hotel, you’ll be able to kick back while enjoying this amazing destination.
Can I find two-bedroom vacation rentals in Historic Kailua Village?
Historic Kailua Village has 61 two-bedroom properties to select from. Go for a vacation home with all the privacy and comfort you need at a price that won’t break the bank on Vrbo.
Are there vacation rentals with WiFi in Historic Kailua Village?
You can choose from 139 vacation rentals with WiFi in Historic Kailua Village. If you want to disconnect from the world on your trip, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Historic Kailua Village?
There are 263 vacation homes with air conditioning in Historic Kailua Village providing that cool, cool breeze and extra bit of comfort. Just enter your desired travel dates and then use our handy filters to help you find properties with air conditioning.
How old do you have to be to rent a vacation rental in Historic Kailua Village?
The minimum age is normally 16, 18 or 21. It can vary from property to property on Vrbo, so check the rules of your chosen Historic Kailua Village vacation home before booking your escape.
How long can I rent a vacation rental in Historic Kailua Village for?
How long you can book a vacation rental in Historic Kailua Village differs according to the property. Just enter your preferred dates to look at a list of options offering extended stays. With loads of creature comforts like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you’re sure to get a perfect place to call your home away from home in Historic Kailua Village.
Does Vrbo offer discounts for vacation homes in Historic Kailua Village?
Whether you’ve got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fantastic bargains and discounts on Vrbo. From short stays to extended vacations, we’ve got the perfect space for your next Historic Kailua Village escape.

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