586+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Windward Coast

Windward Coast pickleball Stays, Resort Rentals, & Homes

About Windward Coast Vacation Rentals

Discover over 586 amazing vacation rental options in Windward Coast 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 Windward Coast.

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 1399.58 ft², with prices averaging US $803 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 Windward Coast.

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Top Pickleball-Ready Accommodation Types in Windward Coast

Type Count
Vacation Homes 395
Holiday Apartments 104
Cottages 47
Villas 25

Use these Quick Filters to Find a Vacation Rental in Windward Coast

★ 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 Windward Coast with PickleTrip™.

Weather in Windward Coast, US

View the weather forecast for Windward Coast before booking your Windward Coast 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 Windward Coast, US

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


Kailua Beach
Lanikai Beach
Waimanalo Beach
Sea Life Park
Kualoa Beach Park
Sandy Beach
Makapuu Beach
Kalama Beach Park
Kane‘ohe Bay
He'eia State Park
Bellows Field Beach Park
Kawainui Park
Royal Hawaiian Golf Club
Kailua Bay Beach
Mokapu Point
Kahaluu Beach
Kaneohe Klipper Golf Course
Ka'a'awa Beach Park
Lanikai Pillboxes Trailhead

Other Places to Stay in Windward Coast, US


Enchanted Lake 411 Properties
Keolu Hills 396 Properties
Coconut Grove 314 Properties
Maunawili 301 Properties
Kailua 265 Properties
Kalama Tract 145 Properties
Lanikai 80 Properties
Kaneohe 37 Properties
Kahalu u 36 Properties
Ka'a'awa 29 Properties
Waimanalo 28 Properties
Waimanalo Beach 28 Properties

Frequently Asked Questions About Windward Coast?

What are the top vacation rentals, resorts, and hotels in Windward Coast 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 Windward Coast. 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 Windward Coast!

How many pickleball-ready properties have private pools in Windward Coast?

Discover 98 accommodations with private or nearby pickleball courts in Windward Coast. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Windward Coast? 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 Windward Coast?

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 586 properties listed in Windward Coast 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 (10) 
Neighborhood Property Count
Eastern Honolulu Vacation Rentals in Windward Coast, US 173
Kalama Tract Vacation Rentals in Windward Coast, US 145
Lanikai Vacation Rentals in Windward Coast, US 80
Hawaii Kai Vacation Rentals in Windward Coast, US 78
Coconut Grove Vacation Rentals in Windward Coast, US 314
Enchanted Lake Vacation Rentals in Windward Coast, US 411
Keolu Hills Vacation Rentals in Windward Coast, US 396
Kuulei Tract Vacation Rentals in Windward Coast, US 432
Kamehame Ridge Vacation Rentals in Windward Coast, US 145
Queens Gate Vacation Rentals in Windward Coast, US 100

People Also Ask

There are 586 Windward Coast, US Vacation Rentals

Recently Booked Vacation Rentals in Windward Coast