37+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Jacksonville
  4. Fleming Island

Fleming Island pickleball Stays, Resort Rentals, & Homes

About Fleming Island Vacation Rentals

Discover over 37 amazing vacation rental options in Fleming Island 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 Fleming Island.

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 991.02 ft², with prices averaging US $290 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 Fleming Island.

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Top Pickleball-Ready Accommodation Types in Fleming Island

Type Count
Vacation Homes 28
Holiday Apartments 4

Use these Quick Filters to Find a Vacation Rental in Fleming Island

★ 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 Fleming Island with PickleTrip™.

Weather in Fleming Island, FL

View the weather forecast for Fleming Island before booking your Fleming Island 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 Fleming Island, FL

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


The Golf Club At Fleming Island
Eagle Harbor Golf Club
Mayo Clinic Florida
St. Johns Town Center
Jacksonville Naval Air Station
TPC Sawgrass
VyStar Veterans Memorial Arena
TIAA Bank Field
World Golf Village
Jacksonville Zoo and Gardens
University of North Florida
Jacksonville University
World Golf Hall of Fame
Daily's Place
Memorial Hospital Jacksonville
Florida Theatre
Orange Park Mall
bestbet Orange Park
Orange Park Medical Center
Cummer Museum of Art and Gardens

Other Places to Stay in Fleming Island, FL


Eagle Harbor Golf Club 71 Properties
The Golf Club At Fleming Island 29 Properties

Frequently Asked Questions About Fleming Island?

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

How many PickleTrip vacation rentals or resorts are available in Fleming Island?

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 37 properties listed in Fleming Island 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 37 Fleming Island, FL Vacation Rentals

Recently Booked Vacation Rentals in Fleming Island