19397+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Port Richey
  4. Highlands

Highlands pickleball Stays, Resort Rentals, & Homes

About Highlands Vacation Rentals

Discover over 19397 amazing vacation rental options in Highlands 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 Highlands.

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 940.25 ft², with prices averaging US $365 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 Highlands.

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Top Pickleball-Ready Accommodation Types in Highlands

Type Count
Vacation Homes 7416
Holiday Apartments 3280
Villas 899
Cottages 181

Use these Quick Filters to Find a Vacation Rental in Highlands

★ 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 Highlands with PickleTrip™.

Weather in Highlands, FL

View the weather forecast for Highlands before booking your Highlands 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

Other Places to Stay in Highlands, FL


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Biggar 626 Properties
Survey Creek 532 Properties
Trailer Estates 520 Properties
Thomas Drive 442 Properties
Ludlam 441 Properties
Bearss Plaza 415 Properties
Braden River 368 Properties

Frequently Asked Questions About Highlands?

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

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

Discover 2743 accommodations with private or nearby pickleball courts in Highlands. Some of the best destinations to stay and play pickleball are:

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

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

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 19397 properties listed in Highlands 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 (3) 
Neighborhood Property Count
Gulf Coast Acres Vacation Rentals in Port Richey, Florida 146
Parkwood Acres Vacation Rentals in Port Richey, Florida 128
Heritage Pines Vacation Rentals in Port Richey, Florida 57

People Also Ask

There are 19397 Highlands, FL Vacation Rentals

Recently Booked Vacation Rentals in Highlands