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

Highpoint pickleball Stays, Resort Rentals, & Homes

About Highpoint Vacation Rentals

Discover over 415 amazing vacation rental options in Highpoint 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 Highpoint.

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 1021.15 ft², with prices averaging US $299 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 Highpoint.

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Top Pickleball-Ready Accommodation Types in Highpoint

Type Count
Vacation Homes 256
Holiday Apartments 37
Villas 7
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Highpoint

★ 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 Highpoint with PickleTrip™.

Weather in Highpoint, FL

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

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


Port of Tampa
Tampa Riverwalk
Tampa Convention Center
Raymond James Stadium
Florida Aquarium
Amalie Arena
Clearwater Marine Aquarium
Lowry Park Zoo
John's Pass Village & Boardwalk
Sand Key Park
Tropicana Field
MacDill Air Force Base
University of Tampa
Salvador Dali Museum
Pier 60 Park
Vinoy Park
Tampa General Hospital
Tampa Bay Downs
George M. Steinbrenner Field
Fort De Soto Park

Other Places to Stay in Highpoint, FL


Shady Lane Village 363 Properties

Frequently Asked Questions About Highpoint?

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

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

Discover 80 accommodations with private or nearby pickleball courts in Highpoint. Some of the best destinations to stay and play pickleball are:

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

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

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 415 properties listed in Highpoint 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 (2) 
Neighborhood Property Count
Shady Lane Master Mhp Vacation Rentals in Highpoint, Florida 368
Shady Lane Village Vacation Rentals in Highpoint, Florida 363

People Also Ask

There are 415 Highpoint, FL Vacation Rentals

Recently Booked Vacation Rentals in Highpoint