44+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Orlando
  4. Winter Springs

Winter Springs pickleball Stays, Resort Rentals, & Homes

About Winter Springs Vacation Rentals

Discover over 44 amazing vacation rental options in Winter Springs 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 Winter Springs.

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 825.46 ft², with prices averaging US $226 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 Winter Springs.

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Top Pickleball-Ready Accommodation Types in Winter Springs

Type Count
Vacation Homes 37
Holiday Apartments 5
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Winter Springs

★ 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 Winter Springs with PickleTrip™.

Weather in Winter Springs, FL

View the weather forecast for Winter Springs before booking your Winter Springs 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 Winter Springs, FL

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


Central Winds Park
Tuscawilla Golf Course
Trotwood Park
Universal Orlando ResortTM
Universal Studios FloridaTM
Orange County Convention Center
Florida Mall
Orlando International Premium Outlets
Amway Center
Camping World Stadium
Holy Land Experience
The Wizarding World of Harry PotterTM
University of Central Florida
The Wheel at ICON ParkTM
Universals Islands of AdventureTM
Mall at Millenia
Pointe Orlando
Orlando Science Center
Universal CityWalk
CoCo Key Water Resort

Other Places to Stay in Winter Springs, FL


Trotwood Park 32 Properties
Central Winds Park 29 Properties
Tuscawilla Golf Course 26 Properties

Frequently Asked Questions About Winter Springs?

What are the top vacation rentals, resorts, and hotels in Winter Springs 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 Winter Springs. 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 Winter Springs!

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

Looking for a fun and active getaway with pickleball courts in Winter Springs? 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 Winter Springs?

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 44 properties listed in Winter Springs in 2026, 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.


People Also Ask

There are 44 Winter Springs, FL Vacation Rentals

Recently Booked Vacation Rentals in Winter Springs