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Discover Your Perfect Upcountry Maui Rentals by Owner

Upcountry Maui Rentals by Owner

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10.0 (3 Reviews)
Apartment
Maui Eco Retreat
  • Parking
  • View
  • Ocean View
View Availability
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9.9 (14 Reviews)
House
Kula 4200
  • Parking
  • View
  • Ocean View
View Availability
More Top-Rated Rentals by Owner in Upcountry Maui Area

Why Choose Rent By Owner for your Upcountry Maui vacation rental?

What makes our Rentals by Owner 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 Upcountry Maui Rentals by Owner

Where are the best neighborhoods to stay in Upcountry Maui?

When exploring Upcountry Maui, Hawaii, you’ll find that choosing the right neighborhood to stay in can greatly enhance your vacation experience. Known for its lush landscapes and tranquil atmosphere, this region offers various charming areas where you can enjoy a peaceful retreat. Whether you prefer the scenic countryside or the picturesque rural communities, each neighborhood provides a unique setting that captures the essence of Upcountry Maui. With Rent By Owner, you can conveniently discover rental by owner options within these neighborhoods, ensuring a trustworthy and seamless booking process for your Hawaiian getaway.

Wailea

In this upscale area, you can enjoy luxurious accommodations and stunning coastal views, making it an ideal choice for a relaxing vacation. The region's high-end rental options provide easy access to world-class beaches and premier dining experiences.

View 1761+ Rentals in Wailea

Haiku

This charming neighborhood offers a tranquil atmosphere perfect for reconnecting with nature while still being close to local amenities. Here, you’ll find a variety of private rentals that let you experience the authentic upcountry Maui lifestyle.

View 73+ Rentals in Haiku

Best Times to Visit Upcountry Maui

When should you plan your Rentals by Owner stay?

Understanding the best time to visit Upcountry Maui ensures you can enjoy its tranquil beauty and favorable weather, making it an ideal choice for your vacation rental here through Rent By Owner.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak tourist season as visitors flock here to enjoy the mild weather and scenic landscapes. Booking your rental by owner early ensures availability during this busy time.

Average Temperature Daytime: 75°F - Nighttime: 60°F
summer
Summer (June to August)

The summer season draws travelers seeking warm weather and outdoor activities. Securing your rental by owner in advance helps you make the most of the high-season atmosphere while enjoying comfortable temperatures.

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

Off-Season Highlights

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Spring (March to May)

In spring, fewer visitors arrive, offering a quieter experience with pleasant weather. This is an ideal time to find rental by owner deals and explore the region without the crowds.

Average Temperature Daytime: 78°F - Nighttime: 62°F
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Fall (September to November)

Fall brings a lull in tourism, making it an excellent period for booking rentals by owner at more affordable rates. The area remains beautiful, with comfortable temperatures and lush natural scenery.

Average Temperature Daytime: 80°F - Nighttime: 63°F

Weekly Weather Forecast for Upcountry Maui

How to Book Your Upcountry Maui vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Upcountry Maui

More Top-Rated Rentals by Owner in Upcountry Maui Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 spacious outdoor gardens or landscaped yards that showcase the region’s lush scenery.
  • Relax by your private or shared outdoor swimming pool, perfect for cooling off after exploring here.
  • Make use of outdoor grilling stations or barbecue areas to savor local flavors under the open sky.
  • Take advantage of covered patios or verandas ideal for outdoor dining and sunset views.
  • Benefit from well-maintained hiking or walking trails nearby that allow you to immerse yourself in nature.
  • Utilize outdoor fire pits or fireplaces for cozy evenings while enjoying the serene surroundings.
  • Capitalize on scenic viewpoints or panoramic decks that highlight the beauty of this destination’s landscape.

Top Attractions Around Upcountry Maui

What attractions are nearby?

While staying in your rental here, you can enjoy a variety of activities nearby, including exploring local farms, visiting scenic mountain viewpoints, and experiencing the tranquil beauty that defines this region of Maui.

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Family Activities

  • Country Farms and Gardens Tour: Explore scenic farms where your family can enjoy fresh produce, learn about local agriculture, and participate in hands-on activities that showcase the region's rich farming traditions.
  • Hiking at Haleakalā Summit: Embark on family-friendly hikes near the summit, offering breathtaking views of the volcanic landscape and opportunities to observe native flora and fauna unique to this area.
  • Visit to the Upcountry Maui Farmers Market: Discover local artisans and farmers at this vibrant market, perfect for sampling island-grown treats and teaching kids about sustainable farming practices in the region.
  • Horseback Riding Adventures: Enjoy scenic trail rides through the upcountry landscape, providing an engaging way for families to experience the natural beauty and tranquility of this destination.
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Adult Activities

  • Visit the Upcountry Maui Farmers Market: Experience fresh local produce and artisanal products at this popular market, perfect for a leisurely morning in the region.
  • Explore Haleakalā National Park's Sunrise Tour: Witness breathtaking sunrises above the clouds by joining a guided tour from here, an unforgettable highlight of your Maui vacation.
  • Attend a Lavender Farm Tour: Discover the aromatic beauty of lavender fields nestled in the area, ideal for relaxation and learning about local agriculture.
  • Participate in a Vineyard or Distillery Visit: Sample handcrafted wines and spirits at nearby vineyards and distilleries, offering a taste of the region’s agricultural heritage.

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Upcountry Maui Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local farms and markets: Take advantage of the region’s agricultural charm by visiting farmers’ markets and farm stands to enjoy fresh, locally sourced products.
  • Embrace outdoor activities: Make the most of the area’s natural beauty by hiking scenic trails, horseback riding, or enjoying peaceful mornings in lush gardens near your rental.
  • Experience authentic cuisine: Savor the flavors of traditional dishes at nearby eateries or prepare meals using ingredients bought from local vendors within your rental’s kitchen.
  • Connect with the community: Engage with friendly locals and attend cultural events to gain a deeper understanding of the area's heritage and traditions.

Transportation Options

  • Rental Cars: You can easily rent a vehicle to explore the scenic landscapes and charming towns of the region at your own pace.
  • Public Buses: Local bus services provide an affordable and convenient way to travel between key points in this area and nearby communities.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick, hassle-free transportation within the region.
  • Bicycle Rentals: Embrace the outdoors by renting bicycles to enjoy the scenic routes and fresh air around here at your leisure.

Local Customs Options

  • Respect for Aloha Spirit: You should approach interactions with warmth and kindness, honoring the local custom of embracing the Aloha spirit that is central to Upcountry Maui's culture.
  • Traditional Hawaiian Protocols: When engaging in cultural events or visiting sacred sites, it’s customary to follow specific etiquette such as removing shoes and speaking respectfully.
  • Festivals and Celebrations: Participating in local festivals offers insight into regional customs, where you can enjoy traditional music, dance, and community gatherings unique to this part of Hawaii.
  • Environmental Respect: Preserving the natural beauty of the area involves practicing sustainable habits, like avoiding littering and respecting native plants and wildlife while exploring here.

Frequently Asked Questions About Upcountry Maui Rentals by Owner

1. What are the top vacation rentals in Upcountry Maui?

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

2. How many Rentbyowner vacation rentals are available in Upcountry Maui?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 55 in the Upcountry 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 Upcountry Maui. 

3. What is the cancellation policy for a rental by owner in Upcountry Maui?

The cancellation policy varies depending on the specific listing. You should review the terms listed on the property page or contact the owner directly to understand the applicable refund and cancellation conditions.

4. How do I confirm the availability of a rental by owner in this area?

Availability details are typically shown on the listing's calendar. To ensure the dates you want are open, it's best to reach out to the owner or booking platform for real-time confirmation.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning, service charges, or local taxes are often included in the listing details. Be sure to review the total price breakdown and communicate with the owner if you have questions.

6. What amenities are usually included in a rental by owner in this region?

Most listings include essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features, refer to the property description or contact the owner to confirm what’s available during your stay.

7. How can I communicate special requests or questions about my stay at an owner-managed rental?

You can contact the owner directly through the messaging system provided by the booking platform. Clear communication helps ensure your needs are met and your stay in this area is enjoyable.

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More Top-Rated Rentals by Owner in Upcountry Maui Area