Historic Kailua Village vacation rentals

We found 871 vacation rentals — enter your dates for availability

Select from 39 houses, 80 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:Mar 6 - Mar 13

Image gallery for Oceanfront Penthouse with Loft!

Terrace/patio
9.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Oceanfront Penthouse with Loft!

Kailua-Kona, HI

5% off
Price is CA $482
CA $4,771 total
includes taxes & fees
Oceanfront Penthouse with Loft!

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Find out more about Historic Kailua Village

Why visit Historic Kailua Village

  • Beautiful Beaches: Enjoy the stunning shores of Kailua Bay and Kahalu'u Bay, perfect for sunbathing and water activities.
  • Historic Sites: Discover the rich history through iconic landmarks and plantation sites in the village.
  • Kailua Pier: Visit this iconic spot for scenic views and opportunities for ocean excursions.
  • Charming Downtown: Stroll through the quaint downtown Kona, filled with local shops and eateries.
  • Outdoor Adventures: Engage in various outdoor activities that cater to both relaxation and excitement.

Popular types of accommodation around Historic Kailua Village

Vrbo offers a variety of vacation rentals in Historic Kailua Village, perfect for every type of traveller. Whether you’re seeking a beautiful condo, a cozy private vacation home, or a spacious villa, you’ll find the ideal spot to unwind. Our customers often choose from stunning Kailua Village condos or charming HI condos to enjoy their stay. Explore your options and discover the perfect home away from home in this picturesque locale.

  • Condos: The top choice for vacation rentals in Historic Kailua Village, offering modern amenities and a convenient location.
  • Houses: Ideal for families or groups, these homes provide a cozy and spacious atmosphere for your getaway.
  • Villas: Luxurious and often featuring stunning views, villas are perfect for a relaxing escape.
  • Apartments: A great option for those seeking comfort and independence during their stay.
  • Cottages: Charming and quaint, cottages offer a unique and homely experience in Historic Kailua Village.**

Top attractions in and around Historic Kailua Village

Historic Kailua Village in Kailua-Kona, Hawaii, offers a delightful mix of outdoor adventures and scenic beauty. Visitors can explore beautiful beaches, the iconic Kailua Pier, and historic plantation sites. This destination is perfect for those seeking a cultural experience combined with beach activities. Whether you're enjoying the ocean views or delving into the area's rich history, there's something for everyone to enjoy in this charming village.

  • Kailua Pier: This lively jetty is the heart of Historic Kailua Village, perfect for embarking on tropical excursions. Enjoy stunning ocean views, watch local fishermen, and catch boat tours that explore the beautiful coastline.
  • Magic Sands Beach: Known for its soft, white sands and vibrant beach vibes, this stunning spot is ideal for sunbathing, swimming, and catching waves. It's a great place to relax and enjoy the sun.
  • Kaloko-Honokohau National Historical Park: A cultural gem, this historic site showcases ancient Hawaiian fishponds and petroglyphs, offering a glimpse into the rich heritage of the islands.

Things to do recommended for couples

For a romantic getaway in Historic Kailua Village, indulge in a delightful meal at KBXtreme, where the atmosphere is perfect for couples. Consider a short drive to Haleo Luau for an enchanting dining experience that showcases Hawaiian culture and cuisine, setting the mood for a memorable evening.

Things to do recommended for families

Your family will delight in the Kona Community Aquatic Center, perfect for splashing around together. Don't miss the Donkey Balls Factory and Store, where you can indulge in sweet treats just 14.5km away, making for a fun and memorable outing for all ages.

Things to do recommended for groups

Explore the Keauhou Shopping Center for shopping and entertainment, just 8.0km from Historic Kailua Village. Enjoy a round of golf at the Big Island Country Club, 4.8km away, or check out Kona Boys Inc, located 14.5km away for unique local finds.

*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, pets, or planning for an extended stay, it's essential to prioritize your preferences when filtering options. Here are some helpful tips for booking on Vrbo.

  • Traveling to Historic Kailua Village with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Historic Kailua Village with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Historic Kailua Village: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring everyone feels at home.
  • Planning for a long term stay visiting Historic Kailua Village: If you're in search of vacation rentals that offer discounts for stays of a month or longer, 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 features like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Historic Kailua Village

Historic Kailua Village, nestled in Kailua-Kona, offers a delightful blend of tropical vibes and family-friendly atmosphere. Explore the charming downtown Kona, unwind at Kailua Bay, and enjoy the stunning scenery of Kahalu'u Bay. This vibrant neighbourhood is perfect for outdoor adventures, making it an ideal spot for tourists seeking both relaxation and excitement. Experience the rich history and natural beauty that make Historic Kailua Village a must-visit destination in Hawaii.

  • Kailua-Kona: Nestled along the western coast of the Big Island, Kailua-Kona is a vibrant city known for its stunning ocean views and rich history. Historic Kailua Village, the cultural heart of the area, offers a delightful blend of shops, restaurants, and historical sites. Visitors can indulge in a variety of outdoor activities, from golfing at world-class courses to exploring nearby beaches and national parks. Don’t miss the chance to snorkel in the crystal-clear waters or enjoy a sunset cruise along the coast, where the scenery is breathtaking.
  • Holualoa Village: Situated a mere 4.8km from Historic Kailua Village, Holualoa Village is a charming community perched in the hills, famous for its coffee farms and artistic vibe. This scenic neighborhood invites you to explore its lush landscapes and art galleries. Outdoor enthusiasts can partake in hiking and golfing while soaking in panoramic views of the coastline. The tranquil atmosphere and local art scene make it an ideal spot for a leisurely day trip or a peaceful afternoon escape.
  • Honokohau: Located 3.2km from Historic Kailua Village, Honokohau is a quaint village that offers a unique blend of adventure and serenity. With its beautiful beaches and proximity to the mountains, it’s a perfect destination for outdoor lovers. Visitors can enjoy golfing, camping, and exploring the nearby shoreline. Honokohau’s untouched natural beauty and welcoming community make it a hidden gem worth visiting during your Hawaiian getaway.

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 simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can really help, as prices often change. Additionally, booking a longer stay typically leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or review and organize your travel plans. You will see your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-ca/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 approximately 421 available throughout the area. These condos are typically situated close to the beach and local shops, providing easy access to attractions like Kailua Beach Park and the stunning Mokulua Islands. Most condos come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and often private balconies to enjoy the tropical surroundings.
Are there any beach house rentals in Historic Kailua Village?
In Historic Kailua Village, Hawaii, there are approximately 900 beach house rentals available, making it a popular destination for travellers seeking a coastal getaway. These beach houses often feature a range of amenities, including fully equipped kitchens, spacious living areas, and private outdoor spaces such as patios or balconies, superb for enjoying the island's stunning views. Many properties are situated near the beautiful Kailua Beach, offering easy access to water activities like swimming, kayaking, and paddleboarding. The village is also close to local shops, restaurants, and cultural attractions, ensuring guests can experience the vibrant local lifestyle while enjoying their beachside retreat.
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 travelling 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.
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.
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 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 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. 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 vacation rental?
March is the most popular time to visit Historic Kailua Village, as it falls within the peak season from January to March. This vibrant period attracts travellers seeking warm weather, beautiful beaches, and the chance to immerse themselves in Hawaiian culture. With average temperatures hovering around the mid-20s Celsius, outdoor activities like swimming, snorkelling, and sightseeing become truly enjoyable. The stunning coastline and lush landscapes provide the superb backdrop for exploration, ensuring you can fully embrace the natural beauty of the area.

During March, visitors can also partake in local festivals and events that showcase the rich history and traditions of the island, adding a unique flavour to your vacation experience. The lively atmosphere, coupled with the welcoming spirit of the community, makes this month particularly special for those looking to engage with the local culture.

If you're considering a more budget-friendly option, October is a fantastic time to visit. This month often sees fewer tourists, allowing for a more relaxed experience while still enjoying the island's charm. The weather remains pleasant, with temperatures typically in the low 20s Celsius, superb for leisurely beach strolls and exploring the quaint shops and eateries in the village.
Are there any remote work vacation rentals in Historic Kailua Village?
In Historic Kailua Village, there are numerous options for remote work vacation rentals, with around 526 available throughout the area. This vibrant destination, known for its stunning beaches and rich history, offers properties that cater specifically to remote workers. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable office spaces, ensuring a productive work environment. Some properties also feature additional conveniences like laptop workspaces, safe storage, and business centres. 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 take part in a unique blend of culture and natural beauty. The Kailua Pier serves as a central point, great for enjoying breathtaking views of the ocean and the surrounding coastline. Nearby, the historic Mokuaikaua Church offers a glimpse into the area's rich heritage and is the oldest Christian church in Hawaii.

For those interested in shopping and dining, the vibrant streets of Kailua Village are lined with local boutiques, art galleries, and eateries, showcasing delicious Hawaiian cuisine. The area also offers easy access to beautiful beaches, such as Kailua Beach and Kaloko-Honokohau National Historical Park, where visitors can relax on the sandy shores or partake in water sports.
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 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 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.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.

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