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Kailua Luxury Rentals

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Kailua Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Kailua 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.

Popular Areas for Kailua Vacation Rentals

Where are the best neighborhoods to stay in Kailua?

Exploring the neighborhoods to stay in Kailua, Hawaii allows you to experience the authentic charm and relaxed vibe of this beautiful coastal town. Whether you prefer a quiet retreat close to pristine beaches or a lively area with local boutiques and eateries, Kailua offers a variety of options to match your vacation style. By choosing the right neighborhood, you'll enjoy convenient access to the natural beauty and welcoming community that make this location a sought-after destination. With trustworthy vacation rentals available, planning your perfect Hawaiian getaway has never been easier.

Lanikai

Known for its pristine beaches and tranquil surroundings, this neighborhood offers a peaceful retreat close to the scenic shoreline, making it ideal for those seeking relaxation and natural beauty.

View 79+ Rentals in Lanikai

Coconut Grove

This charming area provides a cozy community atmosphere with easy access to local shops and outdoor activities, perfect for enjoying the laid-back island lifestyle.

View 314+ Rentals in Coconut Grove

Kalama Tract

Offering a mix of residential comfort and convenient amenities, here you can experience easy access to Kailua’s vibrant town while enjoying a welcoming neighborhood vibe.

View 147+ Rentals in Kalama Tract

Kuulei Tract

Situated close to key beaches and parks, this neighborhood is suited for travelers who wish to explore Kailua’s outdoor attractions from a comfortable base.

View 432+ Rentals in Kuulei Tract

Enchanted Lake

Surrounded by lush greenery and serene water features, this area offers a peaceful environment perfect for unwinding after a day of exploring the region.

View 411+ Rentals in Enchanted Lake

Keolu Hills

Perched on elevated terrain, Keolu Hills presents stunning views and a quiet setting, making it an appealing choice for visitors interested in scenic vistas and exclusivity.

View 396+ Rentals in Keolu Hills

Palolo

Located nearby in Honolulu, this neighborhood grants convenient access to urban attractions while still offering a comfortable place to stay when visiting Kailua and the surrounding regions.

View 140+ Rentals in Palolo

Best Times to Visit Kailua

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as timing your trip to this destination allows you to enjoy pleasant weather and avoid peak crowds in the area.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you'll experience warm weather ideal for beach activities and outdoor exploration in this destination. It's a lively time with increased visitors, making it perfect for those seeking vibrant local events.

Average Temperature Daytime: around 85°F - Nighttime: approximately 75°F
winter
Winter Holidays (December to February)

The holiday season draws visitors looking to enjoy mild winter weather while escaping colder climates elsewhere. You'll find this period offers pleasant days for sightseeing and holiday festivities in the area.

Average Temperature Daytime: about 78°F - Nighttime: near 65°F

Off-Season Highlights

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Spring (March to May)

This springtime period provides a quieter atmosphere, making it an excellent opportunity for relaxing and exploring this region's natural beauty without large crowds.

Average Temperature Daytime: roughly 80°F - Nighttime: around 66°F
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Fall (September to November)

Autumn offers mild weather and fewer visitors, giving you a more peaceful experience while enjoying the scenic vistas of this area. It’s a great time for affordable stays and serene surroundings.

Average Temperature Daytime: approximately 82°F - Nighttime: about 70°F

Weekly Weather Forecast for Kailua

How to Book Your Kailua 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 Kailua

More Top-Rated Vacation Rentals in Kailua 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 outdoor dining areas perfect for al fresco meals in a tropical setting.
  • Relax by private swimming pools that offer a refreshing escape from the sun.
  • Take advantage of lush, landscaped gardens that enhance your outdoor experience.
  • Benefit from shaded lanai spaces ideal for lounging or entertaining al fresco.
  • Make use of outdoor showers to rinse off after beach days in this coastal region.
  • Explore nearby pathways and trails for walking, jogging, or biking through scenic surroundings.
  • Secure parking facilities suited for exploring the area's popular outdoor attractions.

Top Attractions Around Kailua

What attractions are nearby?

Here, you can explore a variety of outdoor activities and water-based adventures just minutes from your vacation rental, making the most of the stunning natural surroundings of this tropical destination.

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Family Activities

  • Hiking at the Koolau Mountains: Explore scenic trails through lush landscapes that offer stunning views and memorable family adventures in this region’s natural beauty.
  • Relaxing on Kailua Beach: Spend a day lounging or swimming in the calm, turquoise waters of the area’s renowned beach, perfect for family fun and picnics.
  • Visiting the Nuuanu Pali Lookout: Enjoy breathtaking vistas from this iconic lookout, providing an educational experience about the area's history and geology for all ages.
  • Exploring local markets and cultural events: Discover vibrant markets and festivals where your family can indulge in regional flavors and learn about the area's rich heritage.
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Adult Activities

  • Snorkeling at Kailua Beach Park: Discover the vibrant marine life just offshore by exploring the clear, inviting waters in this popular destination for water enthusiasts.
  • Hiking the Lanikai Pillboxes: Enjoy panoramic ocean views and lush scenery as you trek to historic military bunkers that offer one of the most scenic overlooks here.
  • Kayaking to the Mokulua Islands: Paddle across calm waters to these picturesque islands, where you can enjoy secluded beaches and spectacular coastal scenery.
  • Shopping and dining in Kailua Town: Immerse yourself in local culture by browsing boutique shops and savoring delicious island cuisine in this charming area.

Other Places to Stay in Kailua, HI

Ulu Po Heiau State Monument
Ulu Po Heiau State Monument Vacation Rentals
Pohakupu
Pohakupu Vacation Rentals
Kuulei Tract
Kuulei Tract Vacation Rentals
Kailua Bay Beach
Kailua Bay Beach Vacation Rentals
Kalama Beach Park
Kalama Beach Park Vacation Rentals
Kawainui Park
Kawainui Park Vacation Rentals
Enchanted Lake
Enchanted Lake Vacation Rentals
Keolu Hills
Keolu Hills Vacation Rentals
Coconut Grove
Coconut Grove Vacation Rentals
Maunawili
Maunawili Vacation Rentals
Kalama Tract
Kalama Tract Vacation Rentals
Lanikai
Lanikai Vacation Rentals
More Places to Stay Near Kailua

Kailua Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local beaches: Take advantage of the area's renowned beaches by planning your days around swimming, sunbathing, or surfing in the warm Hawaiian waters.
  • Visit outdoor markets and eateries: Savor authentic regional flavors and support local vendors at vibrant markets and casual dining spots nearby.
  • Engage in outdoor activities: Make the most of the region’s natural beauty with activities like kayaking, hiking, or paddleboarding suited for all skill levels.
  • Discover hidden gems: Go beyond the typical tourist spots to uncover lesser-known scenic spots and tranquil areas that showcase the true essence of this destination.

Transportation Options

  • Car Rentals: Renting a car provides the most flexibility to explore this scenic region at your own pace, with numerous rental agencies conveniently located nearby.
  • Public Bus Services: The local bus system offers an affordable and eco-friendly way to travel around the area, connecting you to key beaches and attractions.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft offer quick, reliable transportation directly from your vacation rental here.
  • Bicycle Rentals: Biking is an enjoyable and eco-conscious option for discovering the laid-back atmosphere and beautiful scenery of this destination.

Local Customs Options

  • Ho‘okupu: Respectful gift-giving is an important part of local customs, especially when visiting homes or participating in cultural events here.
  • Hoʻoponopono: This traditional Hawaiian practice of reconciliation and forgiveness emphasizes the importance of harmony and respectful communication during your stay.
  • Kākou Spirit: Embracing the communal spirit fosters a sense of unity and shared responsibility among visitors and locals alike in the area.
  • Respect for the ‘Aina: Showing reverence for the land by practicing environmentally conscious behaviors helps preserve the natural beauty of this destination.

Kailua Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Kailua?

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

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

There are 83 vacation rentals with private pools near Kailua. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 443 in the Kailua 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 Kailua. 

5. What is the cancellation policy for vacation rentals in Kailua, Hawaii?

The cancellation policies vary by property. You should review the specific listing details and contact the host directly to understand the terms and any applicable fees or refund conditions.

6. Are there any house rules I should be aware of before booking a vacation rental here?

Yes, each property has its own set of house rules. These can include pet restrictions, noise limitations, and check-in or check-out procedures, so it’s important to read the listing carefully and communicate with the host if you have questions.

7. How do I ensure my booking for a Kailua vacation rental is secure?

Secure bookings are facilitated through trusted platforms that verify listings and protect your payment information. Always book through official channels and contact the host if you need confirmation or further details about the property.

8. What amenities are typically included in vacation rentals here?

Most properties offer amenities like fully equipped kitchens, Wi-Fi, air conditioning, and laundry facilities. Details on specific amenities can be found in each listing, allowing you to select the best fit for your needs.

9. How far in advance should I book a vacation rental in this area?

To secure your preferred property and date, it’s recommended to book several months ahead, especially during peak travel seasons. Availability varies, so early planning helps ensure a smooth reservation process.

Kailua Top Rated Vacation Rentals

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