56+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Jacksonville
  4. Middleburg

Middleburg pickleball Stays, Resort Rentals, & Homes

About Middleburg Vacation Rentals

Discover over 56 amazing vacation rental options in Middleburg 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 Middleburg.

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 871.2 ft², with prices averaging US $218 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 Middleburg.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Middleburg

Type Count
Vacation Homes 41
Holiday Apartments 9
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Middleburg

★ 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 Middleburg with PickleTrip™.

Weather in Middleburg, FL

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

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


St. Johns Town Center
Jacksonville Naval Air Station
VyStar Veterans Memorial Arena
TIAA Bank Field
World Golf Village
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
Prime F. Osborn Convention Center
Metropolitan Park
The Avenues
Jacksonville Equestrian Center
Museum of Science and History

Frequently Asked Questions About Middleburg?

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

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

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

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 56 properties listed in Middleburg 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 (1) 
Neighborhood Property Count
OakLeaf Plantation Vacation Rentals in Jacksonville, Florida 39

People Also Ask

There are 56 Middleburg, FL Vacation Rentals

Recently Booked Vacation Rentals in Middleburg