81+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Oregon
  3. Bend
  4. Southwest Bend

Southwest Bend pickleball Stays, Resort Rentals, & Homes

About Southwest Bend Vacation Rentals

Discover over 81 amazing vacation rental options in Southwest Bend 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 Southwest Bend.

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 1089.11 ft², with prices averaging US $262 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 Southwest Bend.

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Top Pickleball-Ready Accommodation Types in Southwest Bend

Type Count
Vacation Homes 68
Villas 4
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Southwest Bend

★ 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 Southwest Bend with PickleTrip™.

Weather in Southwest Bend, OR

View the weather forecast for Southwest Bend before booking your Southwest Bend 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

Other Places to Stay in Southwest Bend, OR


Bend Factory Stores 2,233 Properties

Frequently Asked Questions About Southwest Bend?

What are the top vacation rentals, resorts, and hotels in Southwest Bend 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 Southwest Bend. 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 Southwest Bend!

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

Looking for a fun and active getaway with pickleball courts in Southwest Bend? 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 Southwest Bend?

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 81 properties listed in Southwest Bend 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 (5) 
Neighborhood Property Count
Century West Vacation Rentals in Bend, Oregon 430
Southern Crossing Vacation Rentals in Bend, Oregon 133
Old Farm District Vacation Rentals in Bend, Oregon 57
Southeast Bend Vacation Rentals in Bend, Oregon 32
Deschutes River Woods Vacation Rentals in Bend, Oregon 31

People Also Ask

There are 81 Southwest Bend, OR Vacation Rentals

Recently Booked Vacation Rentals in Southwest Bend