83+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Hawaii
  3. Upcountry Maui

Upcountry Maui pickleball Stays, Resort Rentals, & Homes

About Upcountry Maui Vacation Rentals

Discover over 83 amazing vacation rental options in Upcountry Maui with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Upcountry Maui.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 673.1 ft², with prices averaging US $553 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Upcountry Maui.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Upcountry Maui

Type Count
Vacation Homes 37
Cottages 15
Holiday Apartments 9
Villas 5

Use these Quick Filters to Find a Vacation Rental in Upcountry Maui

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Upcountry Maui with PickleTrip™.

Weather in Upcountry Maui, HI

View the weather forecast for Upcountry Maui before booking your Upcountry Maui Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Upcountry Maui, HI

PickleTrip offers a large selection of top attractions around Upcountry Maui . Research things to do on your vacation before you visit Upcountry Maui.


Haleakala National Park
Haleakala Crater
Hana Forest Reserve
Kahikinui Forest Reserve
Bamboo Forest
Maui Spa Retreat
Ho'omana Spa Maui
Maui's Winery
Lani Kai Snorkeling
Hosmer Grove
Makaluapuna Point
Kalahaku Overlook
Maui Agricultural Research Center
Hanawi Natural Forest Reserve
Haleakala Bike Company
Hali imaile Farmer's Market
Enlighten Up Massage
Makawao Park
Puuulaula
Maunalei Arboretum

Other Places to Stay in Upcountry Maui, HI


Maui 17,576 Properties
Waiakoa 8,283 Properties
Aliʻi Kula Lavender 7,678 Properties
Kula 7,115 Properties
Sun Yat-sen Park 5,483 Properties
Kaiser Permanente 5,304 Properties
East Maui 308 Properties
Haiku 110 Properties
Pukalani 96 Properties
Haiku 73 Properties
Makawao 30 Properties
Haliimaile 25 Properties

Frequently Asked Questions About Upcountry Maui?

What are the top vacation rentals, resorts, and hotels in Upcountry Maui with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Upcountry Maui. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Upcountry Maui!

How many pickleball-ready properties have private pools in Upcountry Maui?

Discover 2 accommodations with private or nearby pickleball courts in Upcountry Maui. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Upcountry Maui is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Upcountry Maui? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Upcountry Maui?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 83 properties listed in Upcountry Maui in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (2) 
Neighborhood Property Count
Wailea Vacation Rentals in Hawaii 1576
Haiku Vacation Rentals in Hawaii 73

People Also Ask

There are 83 Upcountry Maui, HI Vacation Rentals

Recently Booked Vacation Rentals in Upcountry Maui