Discover Your Ideal Upcountry Maui Vacation Rentals for a Memorable Hawaiian Getaway
Discover Your Perfect Upcountry Maui Vacation Homes
Best Vacation Homes in Upcountry Maui
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Upcountry Maui Luxury Rentals
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Upcountry Maui Pet Friendly Vacation Rentals
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Upcountry Maui Large Vacation Homes
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Why Choose Rent By Owner for your Upcountry Maui Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Upcountry Maui Vacation Rentals
Where are the best neighborhoods to stay in Upcountry Maui?
When exploring Upcountry Maui, Hawaii, choosing the right neighborhood can greatly enhance your vacation experience. This region offers a variety of charming areas that provide a tranquil retreat from the bustling coastline, allowing you to enjoy the scenic beauty and local culture of the island. Whether you're seeking a peaceful setting surrounded by lush landscapes or a convenient base to explore the diverse attractions of Upcountry Maui, you'll find a range of high-quality vacation rentals to suit your preferences. With trusted accommodations available in this picturesque part of the island, you can enjoy an authentic Maui experience while enjoying comfort and ease throughout your stay.
Wailea
In this region, you can enjoy luxurious surroundings and stunning ocean views, making it an ideal spot for a relaxing getaway. Your stay here places you close to world-class beaches and high-end amenities, perfect for a memorable vacation experience.
View 1749+ Rentals in WaileaHaiku
This area offers a tranquil retreat amidst lush landscapes, providing a peaceful environment for your stay in Upcountry Maui. Exploring here means immersing yourself in natural beauty while enjoying easy access to local farms and scenic vistas.
View 73+ Rentals in HaikuBest 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 (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.
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.
Off-Season Highlights
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.
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.
Weekly Weather Forecast for Upcountry Maui
How to Book Your Upcountry Maui Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Upcountry Maui
Common Vacation Rentals Amenities
What amenities can you expect?
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
Top Attractions Around Upcountry Maui
What attractions are nearby?
Nearby, you can enjoy exploring scenic hiking trails, local farms, and charming markets that showcase the natural beauty and vibrant culture of this region.

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.
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.
Other Places to Stay in Upcountry Maui, HI
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?
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:
- Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
- Attached Cottage - Bed & Breakfast RP 220061010000 Permit No.BBMP2015/0001
- Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
- ★Jump Start the road to Hana at Haleakala Cottage-PRIVATE HOT TUB +ACESS TO POOL
- Heaven on Earth in Upcountry Maui
- Rustic yet modern Upcountry retreat with breathtaking views!
- Live Like a North Shore Local~Walk To Coffee/Store, near Road to Hana, Haleakala
- Quaint COTTAGE ~ Walk To Coffee shop, nearby Road to Hana & Haleakala
- Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
- Kula Villa- Spectacular Upcountry views, exclusive and private. 808-283-7370
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?
6. Are there any additional fees or charges I should be aware of when booking a vacation rental here?
7. How do I confirm my reservation and what steps are involved in the booking process?
8. What amenities are generally available in vacation rentals in this region?
9. Is there a minimum stay requirement at vacation rentals in this destination?
Upcountry Maui Top Rated Vacation Rentals
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