973+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Oregon
  3. Portland
  4. Sylvan - Highlands - Southwest Hills

Sylvan - Highlands - Southwest Hills pickleball Stays, Resort Rentals, & Homes

About Sylvan - Highlands - Southwest Hills Vacation Rentals

Discover over 973 amazing vacation rental options in Sylvan - Highlands - Southwest Hills 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 Sylvan - Highlands - Southwest Hills.

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 568.35 ft², with prices averaging US $277 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 Sylvan - Highlands - Southwest Hills.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Sylvan - Highlands - Southwest Hills

Type Count
Vacation Homes 280
Holiday Apartments 251
Cottages 6
Villas 1

Use these Quick Filters to Find a Vacation Rental in Sylvan - Highlands - Southwest Hills

★ 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 Sylvan - Highlands - Southwest Hills with PickleTrip™.

Weather in Sylvan - Highlands - Southwest Hills, OR

View the weather forecast for Sylvan - Highlands - Southwest Hills before booking your Sylvan - Highlands - Southwest Hills 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 Sylvan - Highlands - Southwest Hills, OR


Sylvan-Highlands 837 Properties

Frequently Asked Questions About Sylvan - Highlands - Southwest Hills?

What are the top vacation rentals, resorts, and hotels in Sylvan - Highlands - Southwest Hills 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 Sylvan - Highlands - Southwest Hills. 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 Sylvan - Highlands - Southwest Hills!

How many pickleball-ready properties have private pools in Sylvan - Highlands - Southwest Hills?

Discover 13 accommodations with private or nearby pickleball courts in Sylvan - Highlands - Southwest Hills. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Sylvan - Highlands - Southwest Hills? 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 Sylvan - Highlands - Southwest Hills?

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 973 properties listed in Sylvan - Highlands - Southwest Hills 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 (3) 
Neighborhood Property Count
Sylvan-Highlands Vacation Rentals in Portland, Oregon 837
Arlington Heights Vacation Rentals in Portland, Oregon 1014
West Hills Vacation Rentals in Portland, Oregon 285

People Also Ask

There are 973 Sylvan - Highlands - Southwest Hills, OR Vacation Rentals

Recently Booked Vacation Rentals in Sylvan - Highlands - Southwest Hills