2285+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. St. Petersburg - Clearwater
  4. Clearwater Beach

Clearwater Beach pickleball Stays, Resort Rentals, & Homes

About Clearwater Beach Vacation Rentals

Discover over 2285 amazing vacation rental options in Clearwater Beach 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 Clearwater Beach.

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 929.58 ft², with prices averaging US $428 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 Clearwater Beach.

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Top Pickleball-Ready Accommodation Types in Clearwater Beach

Type Count
Vacation Homes 511
Holiday Apartments 463
Cottages 46
Villas 6

Use these Quick Filters to Find a Vacation Rental in Clearwater Beach

★ 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 Clearwater Beach with PickleTrip™.

Weather in Clearwater Beach, FL

View the weather forecast for Clearwater Beach before booking your Clearwater Beach 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 Clearwater Beach, FL

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


Clearwater Marine Aquarium
Sand Key Park
Pier 60 Park
Beach Walk
Clearwater Beach
Clearwater Beach Jet Ski Guided Tours
Sunsets at Pier 60
Clearwater Municipal Marina
Captain Blighs Landing
Raymond James Stadium
John's Pass Village & Boardwalk
Tropicana Field
Salvador Dali Museum
Vinoy Park
Tampa Bay Downs
George M. Steinbrenner Field
Eckerd College
Big Cat Rescue
Sunken Gardens
Tampa Bay

Other Places to Stay in Clearwater Beach, FL


Clearwater Point 3,675 Properties
Captain Blighs Landing 3,573 Properties
Sand Key Park 3,556 Properties
Clearwater Marine Aquarium 3,523 Properties
Beach Walk 3,433 Properties
Diamond Isle 3,372 Properties
Clearwater Beach Jet Ski Guided Tours 3,349 Properties
Clearwater Municipal Marina 3,336 Properties
Carlouel 1,932 Properties
Bay Esplanade 269 Properties
Sand Key 174 Properties
Island Estate 35 Properties

Frequently Asked Questions About Clearwater Beach?

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

How many pickleball-ready properties have private pools in Clearwater Beach?

Discover 190 accommodations with private or nearby pickleball courts in Clearwater Beach. Some of the best destinations to stay and play pickleball are:

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

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

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 2285 properties listed in Clearwater Beach 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 (6) 
Neighborhood Property Count
Bay Esplanade Vacation Rentals in Clearwater Beach, Florida 269
Sand Key Vacation Rentals in Clearwater Beach, Florida 174
Island Estate Vacation Rentals in Clearwater Beach, Florida 35
Carlouel Vacation Rentals in Clearwater Beach, Florida 1932
Clearwater Point Vacation Rentals in Clearwater Beach, Florida 3675
Diamond Isle Vacation Rentals in Clearwater Beach, Florida 3372

People Also Ask

There are 2285 Clearwater Beach, FL Vacation Rentals

Recently Booked Vacation Rentals in Clearwater Beach