54+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Lakeland - Winter Haven
  4. Highland Park

Highland Park pickleball Stays, Resort Rentals, & Homes

About Highland Park Vacation Rentals

Discover over 54 amazing vacation rental options in Highland Park 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 Highland Park.

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 1036.74 ft², with prices averaging US $206 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 Highland Park.

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Top Pickleball-Ready Accommodation Types in Highland Park

Type Count
Vacation Homes 34
Holiday Apartments 4
Cottages 4
Villas 2

Use these Quick Filters to Find a Vacation Rental in Highland Park

★ 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 Highland Park with PickleTrip™.

Weather in Highland Park, FL

View the weather forecast for Highland Park before booking your Highland Park 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 Highland Park, FL

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


Legoland Florida
Bok Tower Gardens
Lake Kissimmee State Park
Chain of Lakes Park
Southern Dunes Golf and Country Club
Eagle Ridge Mall
Theatre Winter Haven
Southern Dunes Golf Club
Jump Florida Skydiving
Chain Of Wakes
Camp Mack's River Resort Airboat Rides
Indigo's Family Fun Center
Polk County Historical Museum
Mountain Lake
Depot Museum
Grand Hotel
Bartow Flea Market
Northgate Shopping Center
Cypresswood Golf and Country Club
Inman Park

Frequently Asked Questions About Highland Park?

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

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

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

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 54 properties listed in Highland Park 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.


People Also Ask

There are 54 Highland Park, FL Vacation Rentals

Recently Booked Vacation Rentals in Highland Park