Discover Your Perfect Historic Kailua Village Vacation Homes

Best Vacation Homes in Historic Kailua Village

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Historic Kailua Village Luxury Rentals

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Historic Kailua Village Pet Friendly Vacation Rentals

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Historic Kailua Village Large Vacation Homes

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Why Choose Rent By Owner for your Historic Kailua Village Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Historic Kailua Village

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the best of what this destination has to offer, whether you prefer warm weather, quieter crowds, or vibrant local events in the area.

Peak Season Highlights

spring
December to April

During these months, the weather is warm and inviting, making it ideal for exploring this Hawaiian destination’s outdoor activities. The region experiences high visitor demand, so early booking of your vacation rentals is recommended.

Average Temperature Daytime: 80-85°F - Nighttime: 65-70°F
spring
June to August

This period sees the highest influx of travelers seeking to enjoy the sunny days and vibrant atmosphere here. Expect lively local events and a bustling environment, perfect for an energetic vacation experience.

Average Temperature Daytime: 85-90°F - Nighttime: 70-75°F

Off-Season Highlights

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May and November

These shoulder months offer a quieter time to discover the area's natural beauty with fewer crowds. It’s a great opportunity to find more available and potentially more affordable vacation rentals.

Average Temperature Daytime: 78-82°F - Nighttime: 66-69°F
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September to October

As the busy season winds down, the region still enjoys lovely weather, making it suitable for relaxation and sightseeing without the peak season crowds.

Average Temperature Daytime: 81-86°F - Nighttime: 68-72°F

Weekly Weather Forecast for Historic Kailua Village

How to Book Your Historic Kailua Village Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Historic Kailua Village

More Top-Rated Vacation Rentals in Historic Kailua Village Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy access to a private outdoor swimming pool with scenic views of the surrounding area.
  • Relax on a spacious balcony or patio, perfect for taking in the island breeze and ocean vistas.
  • Make use of lush landscaped gardens that offer tranquil outdoor spaces for strolling or picnicking.
  • Take advantage of outdoor grilling areas to prepare meals while enjoying the warm climate and tropical scenery.
  • Utilize secure onsite parking facilities for convenient access during your stay.
  • Benefit from easy access to nearby outdoor water activities such as snorkeling and paddleboarding at the coast.
  • Spend time in designated outdoor recreational areas ideal for yoga, meditation, or simply unwinding in the fresh air.

Top Attractions Around Historic Kailua Village

What attractions are nearby?

In this vibrant area, you can enjoy a variety of activities such as exploring historic sites, relaxing on beautiful beaches, and experiencing local dining options, all just moments away from your vacation rentals in Kailua-Kona’s charming surroundings.

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Family Activities

  • Beach Day at Magic Sands Beach Park: Enjoy a family-friendly day soaking up the sun and playing in the gentle waves just a short drive from the heart of the area.
  • Kona Coffee Farm Tour: Experience an educational and flavorful adventure by visiting local coffee farms that offer engaging tours suitable for all ages.
  • Snorkeling at Keiki Beach: Discover vibrant marine life together while snorkeling in calm, shallow waters perfect for children, right near this popular coastal spot.
  • Historic Kailua Village Walking Tour: Explore the charming streets filled with historic sites, shops, and eateries, providing a memorable cultural experience for the whole family.
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Adult Activities

  • Snorkeling and Diving Tours: Explore the vibrant marine life just off the coast by joining guided snorkeling or diving excursions, a must-do activity in this tropical region.
  • Historical and Cultural Sites: Discover the rich heritage of the area by visiting historic sites that showcase the region's unique past and cultural significance.
  • Sunset Cruises: Enjoy an unforgettable evening on the water with sunset cruises that offer stunning views of the coastline and the opportunity to unwind in style.
  • Local Markets and Art Galleries: Browse through local markets and art galleries to experience the region’s creative spirit and pick up unique souvenirs during your stay.

Other Places to Stay in Historic Kailua Village, HI

Mokuaikaua Church
Mokuaikaua Church Vacation Rentals
Hulihee Palace
Hulihee Palace Vacation Rentals
Kailua Pier
Kailua Pier Vacation Rentals
Kamakahonu Beach
Kamakahonu Beach Vacation Rentals
Kailua-Kona Wharf
Kailua-Kona Wharf Vacation Rentals
KBXtreme
KBXtreme Vacation Rentals
Ahu'ena Heiau
Ahu'ena Heiau Vacation Rentals
Kona Brewing Company
Kona Brewing Company Vacation Rentals
Hulihe‘e Palace State Monument
Hulihe‘e Palace State Monument Vacation Rentals
Mauna Kea Summit
Mauna Kea Summit Vacation Rentals
Kona Community Aquatic Center
Kona Community Aquatic Center Vacation Rentals
Swing Zone
Swing Zone Vacation Rentals
More Places to Stay Near Historic Kailua Village

Historic Kailua Village Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area’s renowned seafood and Hawaiian specialties at nearby restaurants to truly indulge in the region’s flavors during your stay.
  • Visit the Coastal Markets: Frequent the local markets to discover fresh produce, unique souvenirs, and authentic Hawaiian crafts that enhance your experience here.
  • Plan Water Activities: Make the most of the oceanfront location by booking snorkeling, paddleboarding, or sunset cruises to enjoy the region’s stunning maritime scenery.
  • Discover Hidden Gems: Venture beyond the common tourist spots to explore less crowded beaches and scenic overlooks that showcase this destination’s natural beauty.

Transportation Options

  • Rental Cars: You can easily explore the region at your own pace by renting a car, with numerous rental agencies conveniently located nearby.
  • Public Transportation: The local bus system offers an affordable and reliable way to navigate here, connecting key destinations within the area.
  • Taxi Services: Taxis provide flexible transportation options for short trips or travel during late hours in this destination.
  • Bike Rentals: For a scenic and eco-friendly experience, bike rentals are available, allowing you to enjoy stunning views while exploring the region’s historic sites.

Local Customs Options

  • Respect for Aloha Spirit: Embracing the local culture, visitors are encouraged to show kindness and hospitality that embody the heartfelt aloha spirit in every interaction.
  • Traditional Hawaiian Luaus: Participating in or observing luaus provides insight into the region’s rich heritage through authentic cuisine, music, and dance performances.
  • Kāhili Display Customs: Visitors should appreciate the significance of Kāhili, traditional feathered staffs that symbolize royalty and pride here, often displayed during cultural events.
  • Respect for Sacred Sites: When exploring historic areas and temples, it is essential to observe respectful behavior and adhere to guidelines to honor their cultural importance.

Frequently Asked Questions About Historic Kailua Village?

1. What are the top vacation rentals in Historic Kailua Village?

There are a lot of options in Historic Kailua Village. If you plan on staying in the Historic Kailua Village area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Historic Kailua Village:

2. How many vacation rentals have private pools in Historic Kailua Village?

There are 29 vacation rentals with private pools near Historic Kailua Village. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Historic Kailua Village are best for families?

If you are looking for a family-friendly vacation home in Historic Kailua Village, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Historic Kailua Village:

4. How many Rentbyowner vacation rentals are available in Historic Kailua Village?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 855 in the Historic Kailua Village area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Historic Kailua Village. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it's essential to review the specific listing details. You can find this information on the property page or contact the host directly for clarification.

6. How do I secure my reservation at a vacation rental in this region?

Reservations are typically confirmed through the booking platform after you complete the required steps and payment process. Ensure all your details are accurate and communicate with the host if needed for a smooth booking experience.

7. Are there any house rules or restrictions I should be aware of before booking?

Yes, each property may have its own house rules regarding noise, pets, smoking, and occupancy limits. These details are usually outlined in the listing, so reviewing them beforehand will help ensure your stay complies with host expectations.

8. What amenities are commonly included in holiday rentals here?

Most properties offer amenities such as Wi-Fi, fully equipped kitchens, air conditioning, and parking. To confirm specific amenities, please check the individual listing details or contact the host directly.

9. How can I get assistance during my stay if I encounter issues with my accommodation?

Support is generally available through the booking platform's customer service or directly from the property host. Contact details are provided in your reservation confirmation, ensuring you have reliable assistance throughout your stay.

Historic Kailua Village Top Rated Vacation Rentals

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