1314+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Leesburg
  4. The Villages

The Villages pickleball Stays, Resort Rentals, & Homes

About The Villages Vacation Rentals

Discover over 1314 amazing vacation rental options in The Villages 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 The Villages.

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 1652.35 ft², with prices averaging $169 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 The Villages.

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Top Pickleball-Ready Accommodation Types in The Villages

Type Count
Vacation Homes 1005
Villas 265
Cottages 26
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in The Villages

★ 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 The Villages with PickleTrip™.

Weather in The Villages, FL

View the weather forecast for The Villages before booking your The Villages 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 The Villages, FL

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


The Villages Market Square
Spanish Springs Town Square
Orange Blossom Hills Golf & Country Club
Nancy Lopez Legacy Golf & Country Club
Cane Garden Country Club
Lake Deaton
Glenview Champions Country Club
Central Florida Health
AdventHealth
Silver Springs State Park
Ocala Equestrian Complex
Florida Horse Park
Ocala Regional Medical Center
Silver Springs Nature Theme Park
Webster Westside Flea Market
Lakeridge Winery
Ocala Downtown Square
Paddock Mall
Don Garlits Museum of Racing
Grand Oaks Resort and Carriage Musuem

Other Places to Stay in The Villages, FL


Liberty Park 722 Properties
Mallory Square 678 Properties
Santiago 619 Properties
Bonnybrook 617 Properties
Fernandina 605 Properties
Santo Domingo 581 Properties
Lake Sumter Landing 483 Properties
Silver Lake 336 Properties
Lake Deaton 53 Properties
Duval 32 Properties
Virginia Trace 24 Properties
Lynnhaven 24 Properties

Frequently Asked Questions About The Villages?

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

How many pickleball-ready properties have private pools in The Villages?

Discover 73 accommodations with private or nearby pickleball courts in The Villages. Some of the best destinations to stay and play pickleball are:

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

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

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 1314 properties listed in The Villages 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 (16) 
Neighborhood Property Count
Duval Vacation Rentals in Leesburg, Florida 32
Virginia Trace Vacation Rentals in Leesburg, Florida 24
Lynnhaven Vacation Rentals in Leesburg, Florida 24
Liberty Park Vacation Rentals in Leesburg, Florida 722
Mallory Square Vacation Rentals in Leesburg, Florida 678
Bonnybrook Vacation Rentals in Leesburg, Florida 617
Fernandina Vacation Rentals in Leesburg, Florida 605
Lake Sumter Landing Vacation Rentals in Leesburg, Florida 483
Pennecamp Vacation Rentals in Leesburg, Florida 680
Sabal Chase Vacation Rentals in Leesburg, Florida 753
Del Mar Vacation Rentals in Leesburg, Florida 496
Caroline Vacation Rentals in Leesburg, Florida 641
St. Charles Vacation Rentals in Leesburg, Florida 725
Piedmont Vacation Rentals in Leesburg, Florida 319
Bonita Vacation Rentals in Leesburg, Florida 683
Springdale Vacation Rentals in Leesburg, Florida 317

People Also Ask

There are 1314 The Villages, FL Vacation Rentals

Recently Booked Vacation Rentals in The Villages