612+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Leesburg
  4. Wildwood

Wildwood pickleball Stays, Resort Rentals, & Homes

About Wildwood Vacation Rentals

Discover over 612 amazing vacation rental options in Wildwood 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 Wildwood.

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 1827.85 ft², with prices averaging US $190 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 Wildwood.

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Top Pickleball-Ready Accommodation Types in Wildwood

Type Count
Vacation Homes 455
Villas 130
Cottages 8
Holiday Apartments 5

Use these Quick Filters to Find a Vacation Rental in Wildwood

★ 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 Wildwood with PickleTrip™.

Weather in Wildwood, FL

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

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


Continental Country Club
Lake Okahumpka Park
Miona Lake Golf Club
The Villages Market Square
Ocala Equestrian Complex
Florida Horse Park
Ocala Regional Medical Center
Spanish Springs Town Square
Webster Westside Flea Market
Lakeridge Winery
Ocala Downtown Square
Lake Louisa State Park
Paddock Mall
Don Garlits Museum of Racing
Grand Oaks Resort and Carriage Musuem
Lake Dora
Lake Weir
The Country Club Of Silver Springs Shores
Citrus County Speedway
Venetian Gardens

Other Places to Stay in Wildwood, FL


St. Charles 725 Properties
St. James 702 Properties
Buttonwood 605 Properties
Lake Okahumpka Park 593 Properties
Continental Country Club 583 Properties
Miona Lake Golf Club 522 Properties
Coleman 142 Properties
Pennecamp 25 Properties

Frequently Asked Questions About Wildwood?

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

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

Discover 15 accommodations with private or nearby pickleball courts in Wildwood. Some of the best destinations to stay and play pickleball are:

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

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

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 612 properties listed in Wildwood 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 (7) 
Neighborhood Property Count
Duval Vacation Rentals in Leesburg, Florida 39
Pennecamp Vacation Rentals in Leesburg, Florida 25
Buttonwood Vacation Rentals in Leesburg, Florida 605
St. Charles Vacation Rentals in Leesburg, Florida 725
St. James Vacation Rentals in Leesburg, Florida 702
Sunset Pointe Vacation Rentals in Leesburg, Florida 737
Gilchrist Vacation Rentals in Leesburg, Florida 629

People Also Ask

There are 612 Wildwood, FL Vacation Rentals

Recently Booked Vacation Rentals in Wildwood