- Lakeland, FL
- Magician / Family Entertainment
- 13 miles from Winter Haven
- $150-$50,000
Anne M. B. said
“Dan was so full of energy and our five grandchildren thought he was fabulous! We did too! Thanks, Dan!! ”
The 53 Best Family Entertainers for hire in Winter Haven, FL
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310 Family Entertainers serving Winter Haven, FL
- Winter Haven, FL
- Magician / Family Entertainment
- $225.00- 1,500.00
Ana R. said
“Bruce did such an awesome job! We hired him for our daughters first birthday party and it was a blast to have him. He did a really good job involving the kids and adults. I would definitely hire him... ”
- Davenport, FL
- Caricaturist / Family Entertainment
- 13 miles from Winter Haven
- Between $100-$400
Akiva S. said
“A very nice experience. Would highly recommend. ”
- St Cloud, FL
- Balloon Twister / Family Entertainment
- 32 miles from Winter Haven
- $150.00 (varies up to 20 people)
Kristen H. said
“We were thrilled to have a Bruno join us for our Patient Appreciation Fall Fest, and he were incredible! His creativity, speed, and ability to bring smiles to every child was truly impressive. From... ”
- Dade City, FL
- Caricaturist / Family Entertainment
- 37 miles from Winter Haven
- $95- $150
Jennifer C. said
“Tiki did a great job at our event. Everyone loved the experience and we kept her busy the entire 2 hours we had her drawing. ”
- Winter Haven, FL
- Caricaturist / Family Entertainment
- Contact for rates
Leticia R. said
“Olivia is very professional and her work is amazing. I hired her for my daughter's wedding and it was a hit, all our guests loved her work. ”
Stevens Puppets
1 Verified booking- Lake Wales, FL
- Puppet Show / Family Entertainment
- 12 miles from Winter Haven
- $250-$450
Award winning hand-carved wooden marionette (puppets) shows. Perfect for any occasion. Classic children's fairy tales and literature. 45 minutes plus a...
- Davenport, FL
- Face Painter / Family Entertainment
- 13 miles from Winter Haven
- $125-150 per artist, per hour.
Doreen M. said
“Colleen was so much fun! Thank you for making a great memory👍 ”
Fun Factory Inflatables
1 Verified booking- Lakeland, FL
- Party Inflatables / Family Entertainment
- 13 miles from Winter Haven
- $90.00 and up
We are a one stop party rental company with everything from inflatables to balloon bouquets,character visits,tables,chairs,tents, water slides and more.We...
The Black Tie Event Company
4 Verified bookings- Lakeland, FL
- Photo Booths / Family Entertainment
- 13 miles from Winter Haven
- $200 and up
We started The Black Tie Event Company with one goal in mind: Creating beautiful, memorable yet affordable events for the people of the Tampa Bay area. Our wide...
- Lakeland, FL
- Balloon Twister / Family Entertainment
- 13 miles from Winter Haven
- Contact for rates
Steven S. said
“Very creative and great entertainment for all kids at our party. Would highly recommend. ”
- Lakeland, FL
- Face Painter / Family Entertainment
- 13 miles from Winter Haven
- $280 and up
Luanne S. said
“What an awesome company!! Came and worked so hard and the face painting was wonderful!! ”
Los Soldaditos Puppet Show
1 Verified booking- Lakeland, FL
- Puppet Show / Family Entertainment
- 13 miles from Winter Haven
- $550 - $2000.00
We offer educational puppet shows for children and young hearts that feature a multitude of fun-loving puppet characters, a captivating production with artistic...
- Kissimmee, FL
- Balloon Twister / Family Entertainment
- 27 miles from Winter Haven
- Contact for rates
Briana B. said
“Crystal was phenomenal. I have no words every single child was amazed and I had half the parents asking for her card because all the kids wanted her for their birthday parties. Even the teenagers were... ”
Calvin's Toons
1 Verified booking- Kissimmee, FL
- Caricaturist / Family Entertainment
- 27 miles from Winter Haven
- Contact for rates
Hello I'm Calvin the cartoon wizard! Caricature artist and cartoonist extraordinaire! I'm available for private events and more! I’ve been working and drawing...
- Kissimmee, FL
- Face Painter / Family Entertainment
- 27 miles from Winter Haven
- $125/hr-$150/hr
Suzan H. said
“Great job the price was very good and she can work really fast and still do a great and wonderful job ”
- Kissimmee, FL
- Caricaturist / Family Entertainment
- 27 miles from Winter Haven
- Contact for rates
Chelsea B. said
“Mila was the caricature artist I chose to have at my 31st birthday party, and I'm so glad I did!!! She was amazing!!! So professional, kind, and everyone enjoyed her work!!!! Communication with her... ”
- Windermere, FL
- Magician / Family Entertainment
- 35 miles from Winter Haven
- Starting at $700 per event
Nabil T. said
“We recently hired Daniel Giandoni for our corporate event, and he was absolutely incredible! Daniel captivated our audience with his amazing talent, charm, and professionalism. His performance was... ”
- Clermont, FL
- Game Show / Family Entertainment
- 37 miles from Winter Haven
- Contact for rates
Jenessa L. said
“Keith and his team put on a truly EPIC show. The entire audience is engaged and laughing the whole time. They are personable, professional and really know how to bring the fun! I wish I could have... ”
- Clermont, FL
- Face Painter / Family Entertainment
- 37 miles from Winter Haven
- $125/hr - $250/hr
Alyssa M. said
“She was wonderful for our daughter’s 3rd birthday. She was great with the children, her face painting was incredible, and they all loved the balloon animals. She had great communication through the... ”
- Clermont, FL
- Face Painter / Family Entertainment
- 37 miles from Winter Haven
- $125
Yvette W. said
“The best face painting that I have ever seen. Immensely engaging with the children. ”
- Dade City, FL
- Petting Zoo / Family Entertainment
- 37 miles from Winter Haven
- $350 +
Sr.kathleen L. said
“The Representatives from Red River Pony were very professional and easy to work with. The animals were friendly and gentle. It was a very good experience for all who attended. ”
- Groveland, FL
- Photo Booths / Family Entertainment
- 38 miles from Winter Haven
- Contact for rates
Shawn K. said
“I would recommend this company as well as use them again! It added to our event and is such a great memory for our attendees!! ”
- Winter Garden, FL
- Caricaturist / Family Entertainment
- 39 miles from Winter Haven
- Contact for rates
April S. said
“We had an amazing experience at our event! The caricatures were spot-on, fun, and such a hit with all our guests. She worked quickly, captured everyone’s personalities perfectly, and added so much... ”
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About booking Family Entertainment in Winter Haven, FL
Family events come to life with entertainment that delivers fun, laughter, and unforgettable memories for every generation. The right performers set the tone, whether it’s a lively musician or DJ getting everyone dancing, or a magician who amazes kids and adults alike. From face painters and balloon twisters to jugglers, clowns, and interactive games, professional entertainers transform birthdays, picnics, reunions, and community gatherings into joyful celebrations.
The cost of hiring family entertainers in Winter Haven, Florida will vary depending on the type of entertainment, their experience, and the length of the performance. Services like balloon twisting may be cheaper than more involved performances like magic shows. Contact the local acts above to discuss your event and receive a customized quote.
As you explore Winter Haven family entertainers, check out profiles to learn about their party packages, browse photos, and watch promotional videos. Then, read reviews from past clients to see how they’ve brought the fun to similar events. When requesting a quote, communicate things like your event location, audience size, performance space, and desired atmosphere to get the most accurate pricing.
Once you find the performer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book family-friendly entertainment. You can message the acts, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just sit back and let the family fun begin!
Family Entertainment serving the Winter Haven, FL area
These Family Entertainment serve the wider Winter Haven and Polk county area and travel to Cypress Gardens, Eagle Lake, Auburndale, Lake Alfred, Lake Hamilton, Dundee, Waverly, Haines City, Highland City, Alturas, Eaton Park, Bartow, Lake Wales, Polk City, Davenport, Lakeland, Lakeland Highlands, Homeland, Mulberry, Kingsford, Loughman, Babson Park, Poinciana, Kathleen, Fort Meade, Nichols, Intercession City, Bradley, Nalcrest, and Fedhaven.