1704+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. St. Petersburg - Clearwater
  4. Clearwater

Clearwater pickleball Stays, Resort Rentals, & Homes

About Clearwater Vacation Rentals

Discover over 1704 amazing vacation rental options in Clearwater 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.

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 791.77 ft², with prices averaging $263 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.

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Top Pickleball-Ready Accommodation Types in Clearwater

Type Count
Vacation Homes 1025
Holiday Apartments 285
Villas 31
Cottages 13

Use these Quick Filters to Find a Vacation Rental in Clearwater

★ 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 with PickleTrip™.

Weather in Clearwater, FL

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

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


Ruth Eckerd Hall
Bright House Field
Coachman Park
Church of Scientology
Tampa Bay Grand Prix
Eddie C. Moore Softball Complex
Celebration Station
Morton Plant Hospital
Westfield Countryside Mall
St Petersburg College
Clearwater Country Club
Eagle Lake Park
Congo River Golf - Clearwater
Chi Chi Rodriguez Golf Club
Jack Russell Stadium
Moccasin Lake Nature Park
Cove Cay Golf Club
Harborview Center
Cove Cay Country Club
On Top of The World Golf Club

Other Places to Stay in Clearwater, FL


Pinellas County 13,924 Properties
Morton Plant Hospital 3,987 Properties
Harbor Oaks 3,975 Properties
Church of Scientology 3,908 Properties
Windsor Park 1,112 Properties
On Top of The World 842 Properties
Woodgate 772 Properties
Cove Cay 654 Properties
Greenbrook Estates 530 Properties
Forest Wood Estates 449 Properties
Highpoint 422 Properties
Feather Sound 28 Properties

Frequently Asked Questions About Clearwater?

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

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

Discover 293 accommodations with private or nearby pickleball courts in Clearwater. Some of the best destinations to stay and play pickleball are:

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

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

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 1704 properties listed in Clearwater 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 (16) 
Neighborhood Property Count
Feather Sound Vacation Rentals in Clearwater, Florida 28
Barrington Hills Vacation Rentals in Clearwater, Florida 772
On Top of The World Vacation Rentals in Clearwater, Florida 842
Greenbrook Estates Vacation Rentals in Clearwater, Florida 530
Windsor Park Vacation Rentals in Clearwater, Florida 1112
Cove Cay Vacation Rentals in Clearwater, Florida 654
Forest Wood Estates Vacation Rentals in Clearwater, Florida 449
Old Harbor Place Vacation Rentals in Clearwater, Florida 405
Harbor Oaks Vacation Rentals in Clearwater, Florida 3975
Old Clearwater Bay Vacation Rentals in Clearwater, Florida 3552
Charter Oaks Vacation Rentals in Clearwater, Florida 1053
Seville Vacation Rentals in Clearwater, Florida 760
Misty Springs Vacation Rentals in Clearwater, Florida 399
Northwood Vacation Rentals in Clearwater, Florida 388
Shady Lane Master Mhp Vacation Rentals in Clearwater, Florida 368
Shady Lane Village Vacation Rentals in Clearwater, Florida 363

People Also Ask

There are 1704 Clearwater, FL Vacation Rentals

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