Pickleball Leagues Orlando, FL

Silly Pickles runs organized pickleball leagues in Orlando for people who want an easy, social way to play on a regular basis. You sign up as an individual, get placed with players around your level, and come back each week for rotating partners and structured games. It is low-pressure, easy to enjoy, and just organized enough to keep things moving while leaving plenty of room for fun.

Upcoming Pickleball Leagues in Orlando

Where We Play

Our Orlando leagues are held at pickleball venues chosen for good courts, good vibes, and awesome league-night energy.

📍 Crush Yard

7840 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34747

Crush Yard is an indoor pickleball venue that blends pickleball with food, drinks, and a social atmosphere. The space features 10 indoor courts, a pro shop, arcade games, TVs for sports viewing, and a full-service restaurant and sports bar with a self-serve tap wall.

Why People Love Playing in Our Orlando Leagues

We’ve struck the right balance between organized play and low-pressure fun, making each season simple to join and even easier to enjoy.


✔ A comfortable place to learn or return

New players feel supported with on-site intro lessons, and returning rec players feel right at home.


✔ A community vibe without any awkwardness

Rotating partners makes it easy to meet people naturally, without forced socializing. If you’re new to the area, or just looking to make new friends, this league is perfect for you.


✔ Active, engaging games

Our games are a great way to move and stay active — so fun, you forget it’s a workout.


✔ A weekly ritual that fits real life

Most players join because our leagues are simple, consistent, and easy to build into their routine. Can’t make it to game day? No problem — our system enables you to find a sub with just one click.

What To Expect Each Week

  • Regular Season Play

    Most seasons run 6–8 weeks. Details, dates, and times are listed on each league page.

  • Our Ladder Format

    Each week, you’ll play with a new group for one hour at your skill level. Mix and match teammates and opponents each game!

  • Easy Scheduling

    If you need to miss a week, no problem! 📅 Just use our weekly RSVP to let us know. Need a sub? Just click through our system to request one.

  • Weekly scoring

    Submit your points after each league week, and we’ll update your ranking so matchups stay fun and fair. 

  • All Skill Levels Welcome

    Our ladder format means leagues can accommodate all skill levels. All are welcome, whether you’ve never played or are more advanced!

  • Social and Happy Hours

    Every Orlando league has its own happy hours and socials throughout the league 🍻

FAQs - Orlando, Florida Pickleball Leagues

Is this beginner-friendly?

Yes! Beginners are a big part of our Orlando community, and all of our locations!

Our leagues are built for players at every stage of their pickleball journey. All leagues have an intro session on Day 1, and the ladder format helps everyone settle into the right level without feeling overwhelmed.
How does the ladder format work?

Each week, you’ll be placed in a new group of 4 players close to your skill level. Within this group, play mini games to 15 points, rotating partners each round. Simply submit your scores through our system after game play.

Depending on your performance, you’ll either stay at your current level or move up or down the ladder for the following week of play.

We host everyone from beginners to more advanced players, and the ladder naturally sorts people into the right spot!
How do you determine skill level?

You enter your approximate skill level during checkout. If you're a little off, tha's OK! Our ladder format will place you where you belong after game days.
Do you offer open play or drop-ins?

Right now, we focus on structured league play, so sign up for the season to join the fun! Many of the venues we play at also offer open play or court reservations, which you can organize separately if you’re looking to play pickleball outside of league nights.
Are lessons or classes included with the league?

The league itself is built around gameplay, but we do offer an intro session for new players for all leagues! This is included in the league and will teach you the basics of pickleball.

Many people learn quickly just by playing regularly, and a lot of our advanced players are great people willing to provide assistance if needed.
What should I bring?  

Please wear athletic clothes and bring a paddle! Our venues often have rentals, and sometimes we have extras, but it's not always guaranteed. Check in with your League Host on this! If you're in the market for a new one, our Silly Pickles paddles might be calling your name 🤭

We take care of the courts and balls!