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412 Holiday Party Entertainers serving Winter Springs, FL

Featured

Kardenni

4.88 (20)
Top Performer
35 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Rose O. said “We hired Kardenni for a corporate event and he was fantastic. His performance was engaging, seamless, and perfectly suited for a professional audience. He impressed our guests, kept the energy high,...”
Featured

Kevin King

4.97 (133)
Top Performer
273 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Jennifer R. said “Kevin was a wonderful entertainer. He was funny & engaging and the residents thoroughly enjoyed him. I had him help MC the costume contest and pumpkin judging. He did a great job. Would...”
Featured

Mr. Castle's Magic

5.0 (24)
Top Performer
25 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Pat C. said “We hired Mr Castle for my wife’s birthday party. The group was about half children and half adults. We all had such a great time. His show was a great mix of magic, mentalism, and humor. We were blown...”
Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • Orlando, FL
  • Jazz Band / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

John C. said “Alex Sandro and Leo were an absolutely fabulous jazz ensemble. Alex was a consummate pianist Sandro was a fabulous violinist and Leo was the best bassist ever. Everyone thoroughly enjoyed their...”
Featured

Santa Skip

5.0 (61)
Top Performer
146 Verified bookings

  • Orlando, FL
  • Santa Claus / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Brianna S. M. said “He was truly unbelievable between prompt responding to professionalism and best of all realism! The kids and parent both enjoyed Santa Skip! Can’t wait until next season 🎄🎅”
Featured

REAL Beard Central Florida Santa Claus

5.0 (12)
Top Performer
46 Verified bookings

  • Orlando, FL
  • Santa Claus / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Claudine S. said “Santa looked great, our 5 year old was amazed, and had a wonderful time.”
Featured

Magic by Jerry

4.97 (11)
Top Performer
6 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $300

Charlotte said “We truly can’t recommend Jerry more! We host free events for the over 55 community and he helped make our expo a tremendous success! Not only is he super talented with his close up magic (how does...”
Featured

Laurence Francis - The Mind Magician

4.98 (69)
Top Performer
90 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Adria W. said “We were blown away by Laurence! From the moment we booked him, he was collaborative, thoughtful, and committed to making our event special. He incorporated information about our company into his act...”
Featured

Old Saint Nate

5.0 (1)
Top Performer
4 Verified bookings

  • Mount Dora, FL
  • Santa Claus / Holiday Party Entertainment
  • 22 miles from Winter Springs
  • Starts at $250

Jorge R. said “Old Saint Nate was awesome. Did a great job!!! Definitely worth it. All our guests had a great time and loved taking pictures with Santa. Thank you Old Saint Nate, until next year!🥰”
Featured

Santa Savvy and Christmas Entertainment

5.0 (7)
Top Performer
11 Verified bookings

  • Port Orange, FL
  • Santa Claus / Holiday Party Entertainment
  • 36 miles from Winter Springs
  • Starts at $325

Hemavathy R. said “Santa Savvy was the best and all our friends called him the coolest Santa ever!! He really brought the holiday cheer on by his friendliness and kindness! Thank you so much Santa Savvy for your...”
Featured

Nache on Piano

5.0 (7)
15 Verified bookings

  • Maitland, FL
  • Pianist / Holiday Party Entertainment
  • 6 miles from Winter Springs
  • Starts at $200

Kim G. said “Nache was excellent! The guest loved him as well. Played all the songs we requested so gracefully and beautifully. Even learned and played a few songs not on his memorized setlist just for us, which...”
Featured

B. Happie Entertainment, LLC

4.95 (9)
5 Verified bookings

  • Oviedo, FL
  • Magician / Holiday Party Entertainment
  • 6 miles from Winter Springs
  • Contact for pricing

Archana D. said “Excellent job!. For my kids birthday party I hired a magician and he did an awesome job. We had kids of all ages from 1 to 12 and even some teenage kids. He entertained the entire crowd . Definitely...”
Featured

Harrison Jazz Ensemble

4.72 (32)
62 Verified bookings

  • Orlando, FL
  • Jazz Band / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • $1,000 – $2,500 per event

Katy M. said “We were so happy with booking the Harrison Jazz Ensemble made up of Tim Ford on drums/percussion, Chris Smith on Bass, and Ben Allen on piano. Every person watching was full of smiles and was loving...”
Featured

The Dave Capp Project

5.0 (11)
26 Verified bookings

  • Orlando, FL
  • Jazz Band / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Robin D. said “They had our ladies at the luncheon on their feet. I have been going to these luncheons for a while now and we have had music in the past and I have never seen the women get up and dance. Dave on...”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

  • Orlando, FL
  • Jazz Band / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $300

Kelly S. said “Hired for our corporate event. They did a fantastic job from communication to execution to performance. Thanks!”
Featured

  • Orlando, FL
  • Christmas Carolers / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $750

Mary said “Caroling on Wheels was a big hit at our annual tree lighting ceremony. They sang classic Christmas songs and got everyone in the Christmas spirit with their beautiful lit up car costumes. I’m so...”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Orlando, FL
  • Christmas Carolers / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Pete H. said “The Christmas Carolers were outstanding. Their singing brought alot of the Christmas Spirit to our Christmas Party. ”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Orlando, FL
  • Magician / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Kristina T. said “Mike put on an awesome show. He was punctual, prepared and very organized. He was engaging with the crowd and was just an absolute pleasure to be around. Everyone was amazed by his talent. Fun was...”
Featured

WinterBrooke Bar

5.0 (7)
3 Verified bookings

  • Orlando, FL
  • Bartender / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • $650 – $950 per event

Jonny M. said “Thanks again! You made the event fun for everyone! ”
Featured

The 9th Street Jazz Company

5.0 (7)
18 Verified bookings

  • Deltona, FL
  • Jazz Band / Holiday Party Entertainment
  • 14 miles from Winter Springs
  • $600 – $950 per event

Carlee S. said “They were easy to work with, on time, and set the mood for the event. We will definitely book again.”
Featured

Santa Daniel

5.0 (16)
18 Verified bookings

  • Kissimmee, FL
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Winter Springs
  • Contact for pricing

Anita R. said “Santa was a hit. He is very professional and very reasonably priced. I would definitely hire him again. The magic lives on.”
Featured

Santa Dave

5.0 (1)
2 Verified bookings

  • Clermont, FL
  • Santa Claus / Holiday Party Entertainment
  • 30 miles from Winter Springs
  • Contact for pricing

Victory M. A. said “We had an absolutely amazing experience with Santa Dave at our martial arts studio! He did a fantastic job interacting with both the children and adults, making each personalized meet-and-greet...”
Featured

  • Orlando, FL
  • Santa Claus / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $150

Rosanna F. said “They stayed in character throughout the whole evening and even brought little craft items for the children to draw on! They were great with Guest interaction! Will definitely book them again!”
Featured

Coastal Claus, Co.

New member

  • Port Orange, FL
  • Santa Claus / Holiday Party Entertainment
  • 36 miles from Winter Springs
  • Contact for pricing

Seaside Santa and Mrs. Coral Claus are dedicated to bringing holiday cheer to the children and families of Northeast and Central Florida. Serving Volusia and...

Santa Bobby Scuteri

5.0 (9)
Top Performer
19 Verified bookings

  • Longwood, FL
  • Santa Claus / Holiday Party Entertainment
  • 2 miles from Winter Springs
  • Starts at $150

Moore P. said “Santa was incredible from start to finish. He had a great look, a warm personality, and was outstanding with the children. He helped create a fun and memorable experience for everyone at our event. We...”

Erik Branch

5.0 (14)
Top Performer
24 Verified bookings

  • Lake Mary, FL
  • Pianist / Holiday Party Entertainment
  • 4 miles from Winter Springs
  • Starts at $250

Janet A. said “Would have liked more Christmas music.”

Santa’s Endless Season, LLC

5.0 (1)
Top Performer
8 Verified bookings

  • Clermont, FL
  • Santa Claus / Holiday Party Entertainment
  • 30 miles from Winter Springs
  • Contact for pricing

Alesya G. said “Wow. They truly made a dream come true for kids and adults. So interactive and punctual. Thank you for magical evening. ”

Jolly Jme

5.0 (4)
3 Verified bookings

  • Winter Park, FL
  • Mrs. Claus / Holiday Party Entertainment
  • 7 miles from Winter Springs
  • Starts at $150 per hour

Edwin J. said “A true gem! She should be in Hollywood, so kind and attentive! ”

Fil Lorenz Orchestra

4.99 (38)
1 Verified booking

  • Orlando, FL
  • Jazz Band / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Contact for pricing

Kevin R. said “We had the pleasure of having Fil Lorenz Orchestra play at our June wedding in Carmel and they were fantastic! From the very beginning, Fil was super easy to work with and extremely accessible. He...”

Kitchen's Portal

4.97 (27)
47 Verified bookings

  • Orlando, FL
  • Bartender / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $18 per guest

Courtney A. said “Will use again for any of our events. Everyone loved them and they interacted with all of our guest. Absolutely great job and happy to have them as part of our event. ”

Mrs Claus Orlando

New member

  • Orlando, FL
  • Mrs. Claus / Holiday Party Entertainment
  • 12 miles from Winter Springs
  • Starts at $125 per hour

✨ Bring a little extra Christmas magic to your celebration with a Singing Mrs. Claus! 🎄 Create your perfect Mrs. Claus experience with Christmas carols &...

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About booking Holiday Party Entertainment in Winter Springs, FL

The holidays offer special opportunities to create joy and connection with people you care about the most, and the right entertainment can make your celebration truly shine. From Christmas carolers setting a festive mood to Santas delighting children or DJs keeping the dance floor busy, professional entertainers bring the magic that makes a party memorable. Whether you’re planning a large corporate holiday party or a cozy family Christmas party, you can find the right performer to help you create unforgettable moments.

The cost of hiring holiday party entertainers in Winter Springs, Florida will vary depending on the type of holiday entertainment, their experience, and the length of the performance. A short Santa visit at your family Christmas party will cost less than a live band performing at a holiday corporate event. Contact the local entertainers above to discuss your event details and receive a customized quote.

As you search for Winter Springs holiday party entertainers, view their profiles to read about their services, browse photos, and watch promotional videos. Then, check out reviews from past clients to see what it would be like to work with them. When requesting a quote, include key details like the venue, audience size, expected performance time, and event goals to ensure you receive the most accurate pricing.

Once you find the holiday act you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book holiday party entertainers. You can message the performers, 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 relax and let the holiday magic unfold!

Holiday Party Entertainment serving the Winter Springs, FL area

These Holiday Party Entertainment serve the wider Winter Springs and Seminole county area and travel to Longwood, Casselberry, Lake Mary, Fern Park, Altamonte Springs, Maitland, Goldenrod, Heathrow, Oviedo, Winter Park, Eatonville, Sanford, Lockhart, Union Park, Lake Monroe, Chuluota, Orlando, Debary, Geneva, Clarcona, Pine Hills, O Steen, Osteen, Apopka, Deltona, Plymouth, Belle Isle, Ocoee, Sorrento, and Orange City.