Historic Kailua Village vacation rentals

We found 984 vacation rentals — enter your dates for availability

Welcome to Historic Kailua Village, where stunning beachscapes meet rich cultural heritage in a vibrant tropical paradise. Stroll along picturesque shores, explore the historic Mokuaikaua Church, or embark on scenic walking tours that unveil the area's charm. With diverse accommodations ranging from well-appointed condos to luxurious villas, families and groups can find the perfect home base for adventure. Experience the comfort and convenience of a vacation rental, where you can unwind and create lasting memories together.

Holiday rentals with weekly discounts - Historic Kailua Village

Showing deals for:Dec 11 - Dec 18

ocean access from the pool area
view from lanai
 popular complex close to town
well equipped kitchen
Exceptional
(123 reviews)

Oceanfront Condo with Amazing View—King Bed, Lanai, Walk to Town, Free Parking

Kailua-Kona

8% off
$340
$2,380 for 7 nights
All fees included
Oceanfront Condo with Amazing View—King Bed, Lanai, Walk to Town, Free Parking
Living area
Watch the cruise ship sail into the sunset while enjoying dinner on the lanai.
Private kitchen
Living area
Exceptional
(85 reviews)

Direct Oceanfront Condo - Beach- King Bed - Free WiFi

Kailua-Kona

8% off
$319
$2,235 for 7 nights
All fees included
Direct Oceanfront Condo - Beach- King Bed - Free WiFi
Sun, water, and nowhere to be—just slip into the pool, stretch out under the palms, and let the day unfold at its own pace.
Spacious covered lanai with dining and lounge seating, overlooking the garden—perfect for relaxing, reading, or enjoying Kona’s warm evenings.
Spacious great room with seating, dining, and a dedicated workspace—ideal for longer stays or working remotely in comfort.
Open layout connects the living area to the kitchen, making it easy to unwind, cook, or spend time together in a relaxed, airy setting.
Exceptional
(19 reviews)

Walkable Kona Condo Oceanfront Pool Private Lanai

Kailua-Kona

8% off
$207
$1,449 for 7 nights
All fees included
Walkable Kona Condo Oceanfront Pool Private Lanai
Living area
Property grounds
Living area
Property grounds
Exceptional
(34 reviews)

Hale He'e - Octocondo at Alii Drive

Kailua-Kona

7% off
$277
$1,941 for 7 nights
All fees included
Hale He'e - Octocondo at Alii Drive
Room
Living area
Living area
Pool
Exceptional
(7 reviews)

Oceanside King Bed, Private Beach Access, Pool & Lanai in Kona

Kailua-Kona

8% off
$259
$1,814 for 7 nights
All fees included
Oceanside King Bed, Private Beach Access, Pool & Lanai in Kona
Room
Private kitchen
Enjoy the ocean view from the pool area
We love to cook - the kitchen is pretty stocked
Exceptional
(7 reviews)

Enjoy our Big Island Home at desirable Kona Reef Oceanfront condos.

Kailua-Kona

8% off
$285
$1,993 for 7 nights
All fees included
Enjoy our Big Island Home at desirable Kona Reef Oceanfront condos.
Kitchen
View from lanai
Walkway by building #1
Building #1
Exceptional
(103 reviews)

Kona Makai Building #1

Kailua-Kona

5% off
$303
$2,122 for 7 nights
All fees included
Kona Makai Building #1
Kona Reef ocean front pool and spa
Outdoor dining
Interior
Living area
Exceptional
(134 reviews)

Panoramic Oceanfront! Central Air Conditioning! King Bed! Gorgeous Kitchen!

Kailua-Kona

8% off
$467
$3,267 for 7 nights
All fees included
Panoramic Oceanfront! Central Air Conditioning! King Bed! Gorgeous Kitchen!
Private kitchen
view of the pool
Updated kitchen in 2015
Outdoor table and chairs on the lanai
Exceptional
(164 reviews)

Oceanfront 2 BR/2BA in Beautiful Sea Village.

Kailua-Kona

7% off
$300
$2,103 for 7 nights
All fees included
Oceanfront 2 BR/2BA in Beautiful Sea Village.
Living area
Lanai
Pool and Hot Tub
Exterior
Exceptional
(161 reviews)

One Bedroom, First Floor, Fully Furnished Condo

Kailua-Kona

8% off
$175
$1,225 for 7 nights
All fees included
One Bedroom, First Floor, Fully Furnished Condo
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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.

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 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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