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The 9 Best 1920s Era Entertainers for Hire in Winter Park, FL

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69 1920s Era Entertainers serving Winter Park, FL
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1920s Era Entertainment Pricing

Pricing

Using data from quotes sent through GigSalad, we’ve gathered average pricing for hiring 1920s Era Entertainment in your region.

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What Winter Park Users Say

5-star review

“Best band we've had so far!!” – Janet H., reviewing Orlando 1920s Era Entertainer Show Band on Wheels, Theme band with antique car. More reviews

Z Street Speakeasy Band, Gatsby Band, 1920s, 1940s, to Current Hits - Jazz Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner
Z Street Speakeasy Band, Gatsby Band, 1920s, 1940s, to Current Hits - Jazz Band / 1920s Era Entertainment in Orlando, Florida

Z Street Speakeasy Band, Gatsby Band, 1920s, 1940s, to Current Hits

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5.0 (6)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 8 Verified Bookings

Ashley B. said “Z Street was an amazing band to work with! Not only was the band director a wonderful person to work with prior to the event, but the band was also great!…”

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The Vocalitas - 1950s Era Entertainment / 1920s Era Entertainment in Orlando, Florida Featured vendor banner

This vendor provides virtual services Offers Virtual Services

The Vocalitas - 1950s Era Entertainment / 1920s Era Entertainment in Orlando, Florida

The Vocalitas

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5.0 (11)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon 1950s Era Entertainment / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 12 Verified Bookings

Ginalisa R. said “Our residents were so engaged & had a wonderful time! It was truly a wonderful experience!”

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The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner
The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Orlando, Florida

The Gatsby Gang Jazz Band

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5.0 (3)
  • Map pin icon Orlando, FL
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 9 Verified Bookings

Ayodeji B. said “Great evening”

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Safia Valines - Wedding Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Safia Valines - Wedding Band / 1920s Era Entertainment in Orlando, Florida

Safia Valines

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4.99 (46)
  • Map pin icon Orlando, FL
  • Vendor category icon Wedding Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 30 Verified Bookings

Z said “Safia is a Terrific entertainer and great opera singer. Communicative and worldly. Very professional and delivers what she promises. Also, very responsive…”

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Show Band on Wheels, Theme band with antique car - Jazz Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner
Show Band on Wheels, Theme band with antique car - Jazz Band / 1920s Era Entertainment in Orlando, Florida

Show Band on Wheels, Theme band with antique car

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5.0 (4)
  • Map pin icon Orlando, FL
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 3 Verified Bookings

Janet H. said “I'm in charge of the entertainment at our retirement community. I hired Mark and Kathy an their show band on wheels to perform for our event. The people…”

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Brown Bag Brass Band - Brass Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Brown Bag Brass Band - Brass Band / 1920s Era Entertainment in Orlando, Florida

Brown Bag Brass Band

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5.0 (4)
  • Map pin icon Orlando, FL
  • Vendor category icon Brass Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 8 Verified Bookings

Treasure T. said “Joseph did a spectacular job entertaining us at my husbands birthday party! He was professional & personable & I think enjoyed himself as well…”

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Background Jazz Band - Jazz Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner
Background Jazz Band - Jazz Band / 1920s Era Entertainment in Orlando, Florida

Background Jazz Band

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4.85 (9)
  • Map pin icon Orlando, FL
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 22 Verified Bookings

Court K. said “Great band, highly recommend”

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Jazz Band for Holiday Parties - Jazz Band / 1920s Era Entertainment in Orlando, Florida Featured vendor banner
Jazz Band for Holiday Parties - Jazz Band / 1920s Era Entertainment in Orlando, Florida

Jazz Band for Holiday Parties

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0 (0)
  • Map pin icon Orlando, FL
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park

We provide live jazz for Holiday and Christmas Parties!

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Lyn Sky Entertainment - Stilt Walker / 1920s Era Entertainment in Orlando, Florida
Lyn Sky Entertainment - Stilt Walker / 1920s Era Entertainment in Orlando, Florida

Lyn Sky Entertainment

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5.0 (6)
Top Performer badge
  • Map pin icon Orlando, FL
  • Vendor category icon Stilt Walker / 1920s Era Entertainment
  • Travel distance icon 5 miles from Winter Park
  • Check mark icon 14 Verified Bookings

Diane A. said “Lyn provided excellent service, she was prompt, friendly, and professional. She throughly entertained our guests.”

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Show More 1920s Era Entertainers Near You

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Quick facts
1920s Era Entertainment in Winter Park, FL

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1,249 quotes sent

In the past year, 1920s Era Entertainers have sent 1,249 quotes to event planners

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119th most popular

1920s Era Entertainers rank #119 in popularity out of 545 categories on GigSalad

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5 out of 5 stars

560 1920s Era Entertainer reviews on GigSalad with an average rating of 5 stars

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Typically hired for

Birthday Parties in Winter Park

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3 days on average to book

From request to booking, it takes 3 days (on average) to hire 1920s Era Entertainer

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Florida ranks #2

for 1920s Era Entertainer requests in the United States

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1920s Era Entertainment in Winter Park, FL


For black-tie affairs, large corporate events, high-class dinner parties, holiday parties, birthday parties, anniversary parties, supper clubs, or other occasions, bands playing 1920s Musical Entertainment and period music from the roaring twenties can be an excellent entertainment choice. Popular entertainers from this fun-filled decade include Josephine Baker, Al Jolson, George Gershwin, Vaudeville Performers and Harlem Jazz musicians (to name a few). Related searches include Big Bands, Swing Bands, Jazz Bands, Jazz Singers. Start your search by selecting your city above.

Some things to consider when hiring 1920s entertainment is to make sure you listen to audio and watch video clips of the performer/group. This will ensure that you truly do book the best for your next event! Next, you want to get references. Talk to people in the area about the performer and get feedback. Finally, get a contract. Many professional performers require a deposit to secure them at your next event. Make sure to read through the contract carefully before contracting their services for your party. Search for 1920s Era Entertainment in Winter Park, Florida above.

Please note that these 1920s Era 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, O Steen, and Osteen.

Find 1920s Era Entertainment in nearby cities

Altamonte Springs Orlando Casselberry Winter Springs Pine Hills Oviedo
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