Discover Your Perfect Kailua (Maui) Vacation Homes

Kailua (Maui) Luxury Rentals

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Why Choose Rent By Owner for your Kailua (Maui) 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 Kailua (Maui)

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can greatly enhance your experience, as the region offers optimal weather and fewer crowds during certain months, making it the perfect opportunity to enjoy your stay here through carefully selected vacation rentals.

Peak Season Highlights

spring
December to April

During the winter months, the area experiences its peak season, attracting visitors seeking warm weather and ideal conditions for outdoor activities.

Average Temperature Daytime: 75°F to 82°F - Nighttime: 65°F to 71°F
spring
June to August

Summer offers warm, sunny days perfect for exploring and enjoying the beaches, making it a popular time for travelers to visit this destination.

Average Temperature Daytime: 85°F to 89°F - Nighttime: 70°F to 75°F

Off-Season Highlights

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April to June

In the spring, fewer crowds and pleasant temperatures create an excellent opportunity for a relaxed getaway here while avoiding the busiest times of year.

Average Temperature Daytime: 78°F to 83°F - Nighttime: 64°F to 68°F
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September to November

Fall tends to see less tourism, offering a quieter experience with mild weather ideal for exploring the natural beauty of this region without the peak-season crowds.

Average Temperature Daytime: 79°F to 84°F - Nighttime: 65°F to 70°F

Weekly Weather Forecast for Kailua (Maui)

How to Book Your Kailua (Maui) 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 (Maui)

More Top-Rated Vacation Rentals in Kailua (Maui) 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 on a spacious lanai with scenic views of the surrounding landscape.
  • Relax in a private backyard with lush gardens and tranquil seating areas.
  • Take advantage of a beautifully maintained swimming pool for refreshing dips after exploring the area.
  • Stroll along walking paths or hiking trails that weave through the property's picturesque grounds.
  • Host barbecue gatherings using outdoor grills available at many properties here.
  • Unwind in shaded patio areas perfect for morning coffee or evening relaxation.
  • Make use of outdoor showers to rinse off after enjoying nearby beaches or outdoor activities.

Top Attractions Around Kailua (Maui)

What attractions are nearby?

Nearby, you can explore an array of outdoor activities including stunning beaches, scenic hikes, and serene nature spots that showcase the best of this region's natural beauty.

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Family Activities

  • Ho‘okipa Beach Park: Enjoy a family day at this popular beach known for its excellent swimming conditions and picturesque surroundings.
  • Haiku Mill: Explore this historic site to discover the region’s rich sugar plantation history through engaging tours and scenic views.
  • Garden of Eden Arboretum: Wander through lush landscapes that showcase native Hawaiian plants and breathtaking ocean vistas, perfect for a family outing.
  • Hookipa Lookout: Experience stunning panoramic views of the coastline while spotting local sea turtles and surfers from this scenic vantage point.
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Adult Activities

  • Snorkeling at Ahihi Kinau Natural Area Reserve: Discover vibrant marine life and crystal-clear waters just a short drive from your vacation rental, making it a must-do activity here.
  • Hiking the Ho‘olawa Bay Trail: Explore scenic coastal views and lush landscapes along this popular trail, perfect for an adventurous day in the region.
  • Visit the Haiku Gardens: Relax and enjoy the serenity of beautifully maintained gardens, providing a peaceful retreat close to your accommodation.
  • Golf at the Maui Country Club: Tee off amid stunning surroundings on one of the area's top golf courses, ideal for a leisurely day out.

Kailua (Maui) Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local beaches: Take advantage of the pristine shores nearby by visiting less crowded beaches for a relaxing and authentic experience in this region.
  • Visit local markets: Discover fresh produce and unique crafts at the area’s markets, supporting local vendors and immersing yourself in the island’s vibrant culture.
  • Plan outdoor adventures: Maximize your stay by including activities like hiking or snorkeling that showcase the natural beauty of this destination's landscape.
  • Respect local customs: Engage with the community by observing local traditions and practices, ensuring an enriching visit to this welcoming part of Hawaii.

Transportation Options

  • Rental Cars: Renting a vehicle provides the most flexibility to explore the region at your own pace, with numerous rental agencies available nearby.
  • Public Transit: The local bus system offers an affordable and eco-friendly way to navigate the area, connecting key points of interest around this destination.
  • Taxi Services: Taxis are readily available for convenient, door-to-door transportation throughout the region, ideal for short trips or when traveling with luggage.
  • Bike Rentals: Cycling is a popular option here, allowing you to enjoy scenic routes while offering an active and environmentally friendly way to see the surroundings.

Local Customs Options

  • Respect for the Aloha Spirit: Visitors are encouraged to embrace the local ethos of kindness, harmony, and mutual respect that defines the area's welcoming community.
  • Traditional Hawaiian Language: Learning and using basic Hawaiian words and phrases can demonstrate appreciation and foster genuine connections with locals here.
  • Ohana Values: Family and community are central in this destination, so participating in or observing family-oriented customs shows your respect for the region’s cultural core.
  • Native Hawaiian Arts and Crafts: Supporting and appreciating local artisans by engaging with traditional arts such as quilting, jewelry making, or hula is highly valued in this area.

Frequently Asked Questions About Kailua (Maui)?

1. What are the top vacation rentals in Kailua (Maui)?

There are a lot of options in Kailua (Maui). If you plan on staying in the Kailua (Maui) 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 (Maui):

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

There are 1 vacation rentals with private pools near Kailua (Maui). Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Kailua (Maui), 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 (Maui):

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 67 in the Kailua (Maui) 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 (Maui). 

5. What is the cancellation policy for booking a vacation rental in this area?

Cancellation policies vary depending on the property listing. To ensure your plans can be flexible, review the specific cancellation terms provided in the listing details or contact the property owner directly before confirming your reservation.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are common and will be detailed during the booking process. Always check the listing description for a comprehensive fee breakdown before finalizing your reservation.

7. How do I inquire about the availability of a specific vacation rental?

Availability can be checked through the booking platform’s calendar integrated with the listing. For any special requests or questions about dates, reach out directly to the property owner through the messaging feature.

8. What amenities are typically included in vacation rentals in the region?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking. For more specific features such as laundry or outdoor spaces, refer to each listing’s detailed description or contact the owner for confirmation.

9. Is there a minimum stay requirement for booking a vacation rental around this destination?

Minimum night requirements depend on the individual property and the rental period. Details about stay length are clearly outlined in the listing, but feel free to contact the owner if you need accommodations for a specific duration.

Kailua (Maui) Top Rated Vacation Rentals

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