104+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Tampa
  4. Oldsmar

Oldsmar pickleball Stays, Resort Rentals, & Homes

About Oldsmar Vacation Rentals

Discover over 104 amazing vacation rental options in Oldsmar 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 Oldsmar.

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 553.17 ft², with prices averaging US $274 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 Oldsmar.

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Top Pickleball-Ready Accommodation Types in Oldsmar

Type Count
Vacation Homes 45
Holiday Apartments 9
Villas 5

Use these Quick Filters to Find a Vacation Rental in Oldsmar

★ 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 Oldsmar with PickleTrip™.

Weather in Oldsmar, FL

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

December - February
High 75°F       Low 58°F
March - May
High 86°F       Low 61°F
June - August
High 91°F       Low 76°F
September - November
High 89°F       Low 63°F

Top Attractions Around Oldsmar, FL

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


Oldsmar Flea Market
Oldsmar Historical Society Museum
Z - A Specialty Spa
Advanced Primary Care
Busch Gardens Tampa Bay
Port of Tampa
Tampa Riverwalk
University of South Florida
Seminole Hard Rock Casino Tampa
Tampa Convention Center
Raymond James Stadium
Florida Aquarium
Amalie Arena
Clearwater Marine Aquarium
Lowry Park Zoo
John's Pass Village & Boardwalk
Adventure Island
Sand Key Park
Tropicana Field
MacDill Air Force Base

Other Places to Stay in Oldsmar, FL


Z - A Specialty Spa 243 Properties
East Lake Woodlands 191 Properties
Elw Woods Landing 186 Properties
Quail Forest 182 Properties
Oldsmar Historical Society Museum 155 Properties
Advanced Primary Care 147 Properties
Oldsmar Flea Market 143 Properties
Turtle Creek 127 Properties

Frequently Asked Questions About Oldsmar?

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

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

Discover 1 accommodations with private or nearby pickleball courts in Oldsmar. Some of the best destinations to stay and play pickleball are:

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

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

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 104 properties listed in Oldsmar 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 (4) 
Neighborhood Property Count
East Lake Woodlands Vacation Rentals in Tampa, Florida 191
Quail Forest Vacation Rentals in Tampa, Florida 182
Elw Woods Landing Vacation Rentals in Tampa, Florida 186
Turtle Creek Vacation Rentals in Tampa, Florida 127

People Also Ask

There are 104 Oldsmar, FL Vacation Rentals

Recently Booked Vacation Rentals in Oldsmar