Discover Your Perfect Upcountry Maui Vacation Homes

Upcountry Maui Luxury Rentals

Why Choose Rent By Owner for your Upcountry 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 Upcountry Maui

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can significantly enhance your experience, as the best time to vacation here often depends on the weather, local events, and crowd levels in the region’s unique climate cycles.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination experiences its peak season with visitors seeking mild weather and lush scenery, making it an ideal time for exploring and enjoying outdoor activities.

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

The summer months attract travelers looking to experience warm days and vibrant local events, providing perfect conditions for outdoor adventures and cultural festivities in the area.

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

Off-Season Highlights

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Spring (March to May)

Visiting during the spring offers a quieter atmosphere with pleasant temperatures and blooming landscapes, ideal for enjoying peaceful stays in the region's vacation rentals.

Average Temperature Daytime: around 78°F - Nighttime: about 58°F
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Fall (September to November)

In the fall, fewer visitors are present, providing a tranquil environment with comfortable weather—perfect for relaxing stays and exploring at your own pace.

Average Temperature Daytime: approximately 80°F - Nighttime: roughly 62°F

Weekly Weather Forecast for Upcountry Maui

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.

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

  • Access to spacious outdoor patios or decks perfect for relaxing and enjoying the scenic views
  • Private gardens or lush landscaping that showcase the region’s natural beauty
  • Barbecue grills available for outdoor cooking and gatherings in the fresh mountain air
  • Ample outdoor seating areas to unwind and take in the serene surroundings
  • Well-maintained walking trails or paths for exploring the area's natural terrain
  • Outdoor fire pits ideal for cozy evenings under the stars
  • Swimming pools or hot tubs to enjoy the temperate climate in comfort and style
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Family Activities

  • Visit the Maui Pineapple Tour: Learn about pineapple farming and enjoy fresh pineapple tastings at this engaging family-friendly activity in the region.
  • Explore Haleakalā National Park: Witness breathtaking sunrises or hike through stunning landscapes in the nearby national park, perfect for outdoor adventures with your family.
  • Discover the Ali’i Kula Lavender Farm: Stroll through beautiful lavender fields and participate in family-friendly events that highlight the region’s natural beauty.
  • Attend a local farmers market: Experience authentic regional flavors and find unique handmade goods while spending quality time together here in the area.
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Adult Activities

  • Visit the Maui Wine Tasting Room: Discover local wines amidst scenic vineyard views that showcase the region’s rich agricultural heritage.
  • Explore Haleakalā National Park: Experience breathtaking sunrise vistas and unique volcanic landscapes that define this area's natural beauty.
  • Tour Local Farms: Engage in farm tours to learn about traditional Hawaiian agriculture and sample fresh, regionally grown produce.
  • Hike through Upcountry Trails: Enjoy peaceful hikes along scenic trails that highlight the lush scenery and diverse flora of the area.

Upcountry Maui Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local markets and farms: Visiting the area’s farmers’ markets allows you to experience fresh, regional produce and support local vendors during your stay.
  • Plan outdoor activities early in the morning: Take advantage of the region’s pleasant climate by scheduling hikes or scenic drives during the cooler early hours for a more enjoyable experience.
  • Travel off the beaten path: Discover hidden gems and less crowded spots by venturing into the lesser-known parts of this destination, enhancing your overall visit.
  • Stay in unique vacation rentals: Choosing a thoughtfully curated property here provides a comfortable retreat that immerses you in the local culture while enjoying modern amenities.

Transportation Options

  • Rental Car Services: Renting a vehicle offers you the flexibility to explore the scenic landscapes and charming towns scattered throughout this region at your own pace.
  • Public Buses: The local bus system provides an economical and convenient way to get around the area, connecting key points of interest with ease.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available here, offering quick transportation for your adventures in the region.
  • Safari Tours and Shuttle Services: Guided tours and shuttle services can enhance your experience by taking you directly to popular destinations within this part of the island.

Local Customs Options

  • Respect for the Aloha Spirit: Embrace the local tradition of aloha by greeting others with genuine warmth and kindness, which is central to the area's culture.
  • Traditional Hawaiian Luaus: Participate in or observe a luau to experience authentic Hawaiian music, dance, and cuisine that are integral to the region's community celebrations.
  • Respect for Native Land and Sacred Sites: Exercise reverence when visiting historical or sacred locations by following guidelines and honoring local customs.
  • Environmental Stewardship: Practice eco-friendly habits such as proper waste disposal and conservation efforts to preserve the natural beauty of this tranquil destination.

Frequently Asked Questions About Upcountry Maui?

2. How many vacation rentals have private pools in Upcountry Maui?

There are 2 vacation rentals with private pools near Upcountry Maui. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Upcountry Maui are best for families?

If you are looking for a family-friendly vacation home in Upcountry 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 Upcountry Maui:

4. 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 83 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. 

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

Cancellation policies vary depending on the individual property listing. It’s best to review the specific rental's cancellation terms and conditions directly on the listing before booking or contact the property owner for detailed information.

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

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the listing details. To ensure transparency, review the full pricing breakdown on the property page or reach out to the owner for clarification.

7. How do I confirm my reservation and what steps are involved in the booking process?

To confirm your reservation, you will need to complete the booking through the listing platform, providing necessary details and payment. Once confirmed, you will receive a confirmation email with check-in instructions and contact information for the property owner.

8. What amenities are generally available in vacation rentals in this region?

Most properties offer key amenities such as fully equipped kitchens, Wi-Fi, parking, and outdoor spaces. Specific amenities can vary, so it's advisable to check the listing descriptions thoroughly and contact the owner if you have particular needs.

9. Is there a minimum stay requirement at vacation rentals in this destination?

Minimum stay requirements differ by property. Some rentals may have a set number of nights for booking, especially during peak seasons. Check the listing details or contact the owner directly to confirm the minimum stay period.

Upcountry Maui Top Rated Vacation Rentals