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The 86 Best Family Entertainers for Hire in Winter Park, FL

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202 Family Entertainers serving Winter Park, FL
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Game Show Trivolution - Game Show / Family Entertainment in Orlando, Florida Featured vendor banner
Game Show Trivolution - Game Show / Family Entertainment in Orlando, Florida

Game Show Trivolution

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5.0 (5)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Game Show / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 4 Verified Bookings

Jennifer K. said “Jim and GST were fabulous to work with - provided fun and an opportunity for our whole group to be involved as well as worked with our budget and timeframe…”

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Laurence Francis - The Mind Magician - Magician / Family Entertainment in Orlando, Florida Featured vendor banner
Laurence Francis - The Mind Magician - Magician / Family Entertainment in Orlando, Florida

Laurence Francis - The Mind Magician

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4.96 (45)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 48 Verified Bookings

Tara V. said “Laurence came over to help us celebrate our son’s 16th birthday! We warned him about the crowd of teenagers that would be present and that didn’t scare…”

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Mike Valentine Caricature Artist - Caricaturist / Family Entertainment in Orlando, Florida Featured vendor banner
Mike Valentine Caricature Artist - Caricaturist / Family Entertainment in Orlando, Florida

Mike Valentine Caricature Artist

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4.98 (75)
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  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 155 Verified Bookings

Antonio G. said “Mike was amazing, he is top notch! Made my sons 1 st birthday so special!!”

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Kevin King - Magician / Family Entertainment in Orlando, Florida Featured vendor banner
Kevin King - Magician / Family Entertainment in Orlando, Florida

Kevin King

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4.96 (103)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 200 Verified Bookings

Nichole L. said “Everything was great”

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WoodStock Stables - Petting Zoo / Family Entertainment in Apopka, Florida Featured vendor banner
WoodStock Stables - Petting Zoo / Family Entertainment in Apopka, Florida

WoodStock Stables

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5.0 (16)
Top Performer badge
  • Map pin icon Apopka, FL
  • Vendor category icon Petting Zoo / Family Entertainment
  • Travel distance icon 13 miles from Winter Park
  • Check mark icon 23 Verified Bookings

Shaun C. B. said “We hired Woodstock Stables for a birthday party farm petting zoo, and everyone had a wonderful time. The animals were adorable and extremely well behaved,…”

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Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Orlando, Florida Featured vendor banner
Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Orlando, Florida

Mega Magic- Magician Mike D'Urzo

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5.0 (14)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 10 Verified Bookings

Kat D. said “We had several days of meetings and booked Mike to entertain our group before the closing awards dinner. Mike was a true professional and an absolute…”

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Gameshow Group - Game Show / Family Entertainment in Orlando, Florida Featured vendor banner
Gameshow Group - Game Show / Family Entertainment in Orlando, Florida

Gameshow Group

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5.0 (1)
  • Map pin icon Orlando, FL
  • Vendor category icon Game Show / Family Entertainment
  • Travel distance icon 5 miles from Winter Park

Shannon S. said “What a great time. These guys really try to make the event lots of fun. Would recommend!”

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Face & Body Painting By Char Marie - Face Painter / Family Entertainment in Orlando, Florida
Face & Body Painting By Char Marie - Face Painter / Family Entertainment in Orlando, Florida

Face & Body Painting By Char Marie

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5.0 (14)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 31 Verified Bookings

Natalie G. said “Char was amazing at our preschooler’s bday party. The kids loved her and her designs, and she was great to work with. Highly recommend!”

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Leo'z Arts and Photography - Caricaturist / Family Entertainment in Orlando, Florida
Leo'z Arts and Photography - Caricaturist / Family Entertainment in Orlando, Florida

Leo'z Arts and Photography

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4.94 (45)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 92 Verified Bookings

Babette F. said “they did a great job. Our attendees loved it”

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Bruce Stevenson - Caricaturist & Musician - Caricaturist / Family Entertainment in Orlando, Florida
Bruce Stevenson - Caricaturist & Musician - Caricaturist / Family Entertainment in Orlando, Florida

Bruce Stevenson - Caricaturist & Musician

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4.87 (3)
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 5 Verified Bookings

Kelly R. said “I hired Bruce for my husband's 50th birthday party. While guests mingled, they were able to have their caricature created and during dinner, Bruce…”

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Marsha Eaton Caricatures - Caricaturist / Family Entertainment in Orlando, Florida
Marsha Eaton Caricatures - Caricaturist / Family Entertainment in Orlando, Florida

Marsha Eaton Caricatures

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5.0 (6)
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 10 Verified Bookings

Dianne N. said “We contracted with Marsha Eaton to draw for my granddaughter's 10th birthday party being held at a local roller skating rink with a Grease theme.…”

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Jacki Manna, Ventriloquist, Magician, and Face Painter - Face Painter / Family Entertainment in Oviedo, Florida
Jacki Manna, Ventriloquist, Magician, and Face Painter - Face Painter / Family Entertainment in Oviedo, Florida

Jacki Manna, Ventriloquist, Magician, and Face Painter

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5.0 (204)
  • Map pin icon Oviedo, FL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 9 miles from Winter Park
  • Check mark icon 5 Verified Bookings

Asli H. said “My son did love Ms. Jacki’s show at Pineapple Cove Classical Academy’s summer camp two years in a row so we planned to celebrate his 7th birthday with…”

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Balloons by Eva - Balloon Twister / Family Entertainment in Orlando, Florida
Balloons by Eva - Balloon Twister / Family Entertainment in Orlando, Florida

Balloons by Eva

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5.0 (3)
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  • Map pin icon Orlando, FL
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Pedro F. said “Arrived on time, was very professional and had great interaction skills with the kids.”

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Connor Hayes FX - Face Painter / Family Entertainment in Orlando, Florida
Connor Hayes FX - Face Painter / Family Entertainment in Orlando, Florida

Connor Hayes FX

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5.0 (1)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Gary O. said “he was on time and did a great job”

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BRUNO BALLOON-O - Balloon Twister / Family Entertainment in Orlando, Florida
BRUNO BALLOON-O - Balloon Twister / Family Entertainment in Orlando, Florida

BRUNO BALLOON-O

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5.0 (15)
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  • Map pin icon Orlando, FL
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 19 Verified Bookings

Sondra P. said “We had a great experience with Bruno Balloon-o! He was on time, had fun with the kids and made fun balloon animals and swords!”

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DfilmK Productions - Photo Booths / Family Entertainment in Orlando, Florida
DfilmK Productions - Photo Booths / Family Entertainment in Orlando, Florida

DfilmK Productions

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5.0 (16)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Photo Booths / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 23 Verified Bookings

Keren O. said “DfilmsK Production not only captured the essence of the evening, but they also sought to know the details before the event. Ensuring they would be prepared…”

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Bobby the Balloon Man - Balloon Twister / Family Entertainment in Longwood, Florida
Bobby the Balloon Man - Balloon Twister / Family Entertainment in Longwood, Florida

Bobby the Balloon Man

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5.0 (8)
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  • Map pin icon Longwood, FL
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 7 miles from Winter Park
  • Check mark icon 10 Verified Bookings

Kendra G. said “Bobby was exactly what we needed. He was professional, showed up on time, and the balloon art was amazing!!! Heard over and over from our customers how…”

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Danny H Magician - Magician / Family Entertainment in Winter Park, Florida
Danny H Magician - Magician / Family Entertainment in Winter Park, Florida

Danny H Magician

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5.0 (1)
  • Map pin icon Winter Park, FL
  • Vendor category icon Magician / Family Entertainment
  • Check mark icon 1 Verified Booking

Thamia N. said “Danny is a class act. He has a way of entertaining both children and adults. His show is amazing and his personality makes it feel he is on a BIG stage.…”

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Orlando Fun Face - Face Painter / Family Entertainment in Altamonte Springs, Florida
Orlando Fun Face - Face Painter / Family Entertainment in Altamonte Springs, Florida

Orlando Fun Face

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5.0 (3)
  • Map pin icon Altamonte Springs, FL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 12 Verified Bookings

Gary O. said “Very good”

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Magician Cesar Domico - Magician / Family Entertainment in Orlando, Florida
Magician Cesar Domico - Magician / Family Entertainment in Orlando, Florida

Magician Cesar Domico

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5.0 (1)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 2 Verified Bookings

Logan W. said “Truly one of kind talented Artist who conjured out of his magical box of gems a unique show that brought laughter and hysterics to the audience. Cesar…”

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Paul Thomey - Magical Dimensions - Magician / Family Entertainment in Orlando, Florida
Paul Thomey - Magical Dimensions - Magician / Family Entertainment in Orlando, Florida

Paul Thomey - Magical Dimensions

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5.0 (2)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Morris S. said “We're back. We had such a great time with Paul's 2 hours of magic in 2019 for my wife's 60th. We has him back for 3 hours this time. Again…”

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Magic Andy - Magician / Family Entertainment in Orlando, Florida
Magic Andy - Magician / Family Entertainment in Orlando, Florida

Magic Andy

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5.0 (33)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 26 Verified Bookings

Claudia O. said “We were very fortunate to have found Andy to perform in our Children’s bday party. We were all very amazed and stunned to see his magic tricks... my kids…”

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Caricature Com Inc - Caricaturist / Family Entertainment in Orlando, Florida
Caricature Com Inc - Caricaturist / Family Entertainment in Orlando, Florida

Caricature Com Inc

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4.60 (1)
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Mary P. said “Very talented artist. Arrived early, completed all guests names and cleaned up quickly. A definite hit with guests.”

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Ari Novick Magic - Magician / Family Entertainment in Orlando, Florida
Ari Novick Magic - Magician / Family Entertainment in Orlando, Florida

Ari Novick Magic

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5.0 (8)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Ken M. said “Watching Ari work a crowd is truly a magical experience, especially when you're right in the middle of it and can't believe your eyes, wow!”

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FunBox Photo Booths - Photo Booths / Family Entertainment in Orlando, Florida
FunBox Photo Booths - Photo Booths / Family Entertainment in Orlando, Florida

FunBox Photo Booths

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0 (0)
  • Map pin icon Orlando, FL
  • Vendor category icon Photo Booths / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 4 Verified Bookings

We offer state of the art, touchscreen photo booth services to meet the needs of any party or event. Owner Will Lesnick utilizes his decades of media production…

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Cartoon You Caricatures - Caricaturist / Family Entertainment in Orlando, Florida
Cartoon You Caricatures - Caricaturist / Family Entertainment in Orlando, Florida

Cartoon You Caricatures

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5.0 (7)
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 17 Verified Bookings

Megan D. said “Everyone raved and was so excited to have something fun to remember the party! Such an amazingly talented guy not to mention personable.”

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FabulousFacesByFabi - Face Painter / Family Entertainment in Orlando, Florida
FabulousFacesByFabi - Face Painter / Family Entertainment in Orlando, Florida

FabulousFacesByFabi

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5.0 (5)
  • Map pin icon Orlando, FL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 10 Verified Bookings

Ariana K. said “Fabi was so kind and professional. I was blown away by her face painting skills. All the kids loved their face paint and so much fun playing with the…”

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Erick Olson - Magician / Family Entertainment in Orlando, Florida
Erick Olson - Magician / Family Entertainment in Orlando, Florida

Erick Olson

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5.0 (3)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 4 Verified Bookings

Nancy C. said “Terry Ward had just the right amount of energy and humor for our group, He did a great job reading the room and getting all involved. We were highly impressed…”

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John Kinney - Magician / Family Entertainment in Orlando, Florida
John Kinney - Magician / Family Entertainment in Orlando, Florida

John Kinney

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5.0 (2)
  • Map pin icon Orlando, FL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 1 Verified Booking

Jack L. said ““John’s amazing sleight of hand and quick-witted presentation made our event an unforgettably exciting evening. My guests thought John’s performance was…”

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Nef Melendez - Caricaturist / Family Entertainment in Orlando, Florida
Nef Melendez - Caricaturist / Family Entertainment in Orlando, Florida

Nef Melendez

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4.96 (26)
  • Map pin icon Orlando, FL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 53 Verified Bookings

Amber P. said “We hired We Draw The Crowd for our corporate event and he was a HIT!!! It is not only a fun entertainment option to have for your event, but we were able…”

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Family Entertainment in Winter Park, FL


Finding entertainment that’s full of variety and fun for all ages doesn’t have to be difficult. You just have to know where to start!

First, you’ll want to determine what your event needs. For small celebrations, strolling performers are a popular option for creating a fun atmosphere. For bigger gatherings, carnival games and inflatables are a big hit! Once you’ve determined what type of entertainment to book, search online for professionals in your area. Most entertainers and vendors have online profiles that show their services, and many offer various party packages to fit your budget. Check out performance descriptions and photos, and if possible, read through reviews from their past clients. When you’re ready to contact an entertainer for their rates and availability, make sure to give them as much information about your event as possible. Discuss important details such as performance space, power supply, expected number of guests, and any unique aspect of your event. The more info you give the professional, the easier it is for them to provide a customized quote. Lastly, confirm the agreement and details in writing. With GigSalad, everything you need to find and book family entertainment is in one simple platform. Browse profiles, get free quotes, and book with the added security of our Worry-Free Guarantee! Search for Family Entertainment in Winter Park, Florida above.

Please note that these Family Entertainment may also travel to Maitland, Eatonville, Goldenrod, Fern Park, Lockhart, Union Park, Longwood, Belle Isle, Clarcona, Lake Mary, Heathrow, Gotha, Mid Florida, Chuluota, Windermere, Philips, Plymouth, Winter Garden, Geneva, Hunter's Creek, Lake Monroe, Oakland, Zellwood, Debary, Killarney, Lake Buena Vista, Sorrento, Christmas, Osteen, and O Steen.

Find Family Entertainment in nearby cities

Altamonte Springs Orlando Casselberry Winter Springs Pine Hills Oviedo
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