111+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Sarasota
  4. Osprey

Osprey pickleball Stays, Resort Rentals, & Homes

About Osprey Vacation Rentals

Discover over 111 amazing vacation rental options in Osprey 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 Osprey.

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 715.21 ft², with prices averaging US $260 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 Osprey.

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Top Pickleball-Ready Accommodation Types in Osprey

Type Count
Vacation Homes 59
Holiday Apartments 23
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Osprey

★ 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 Osprey with PickleTrip™.

Weather in Osprey, FL

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

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F

Top Attractions Around Osprey, FL

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


Oscar Scherer State Park
Historic Spanish Point
The Oaks Club
Nancy's Consignments
Lido Beach
Venice Beach
Siesta Key Beach
St. Armands Circle
Englewood Beach
Turtle Beach
IMG Academy
Nokomis Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art
Manasota Beach
Crescent Beach
Caspersen Beach
Siesta Key Marina

Other Places to Stay in Osprey, FL


Historic Spanish Point 766 Properties
Nancy's Consignments 744 Properties
The Oaks Club 719 Properties
Sorrento Shores 464 Properties
Oscar Scherer State Park 446 Properties
Rivendell 319 Properties
Bay Acres 316 Properties
Osprey Village 48 Properties

Frequently Asked Questions About Osprey?

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

How many pickleball-ready properties have private pools in Osprey?

Discover 8 accommodations with private or nearby pickleball courts in Osprey. Some of the best destinations to stay and play pickleball are:

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

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

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 111 properties listed in Osprey 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
Vamo Vacation Rentals in Sarasota, Florida 64
Palmer Ranch Vacation Rentals in Sarasota, Florida 38
Bay Acres Vacation Rentals in Sarasota, Florida 316
Sorrento Shores Vacation Rentals in Sarasota, Florida 464
Rivendell Vacation Rentals in Sarasota, Florida 319

People Also Ask

There are 111 Osprey, FL Vacation Rentals

Recently Booked Vacation Rentals in Osprey