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Orlando, FL 
1950s Era Entertainment / 1920s Era Entertainment 
5 miles from Winter Park 
1 Verified Booking Issy D. said “LOVED THEM! THEY DID SUCH AN AMAZING JOB! WILL HIRE AGAIN!”
Orlando, FL
Jazz Band / 1920s Era Entertainment
5 miles from Winter Park
3 Verified Bookings Nicole K. said “We contracted to do a 88th birthday for my dad. This group was amazing - they worked very hard with me to coordinate and be flexible around the weather.…”
Offers Virtual Services
Orlando, FL
Brass Band / 1920s Era Entertainment
5 miles from Winter Park
6 Verified Bookings Jeromy R. said “The guests for the banquet we hosted Loved this band! We appreciated their timeliness and ease of communication before the event!”
Offers Virtual Services
Orlando, FL
Jazz Band / 1920s Era Entertainment
5 miles from Winter Park
1 Verified Booking Kari W. said “I hired the Z Street Speakeasy Band for a last-minute Gatsby themed cocktail party. All I can say is WOW! I would give them 6 stars if I could. They were…”
Orlando, FL
Singing Group / 1920s Era Entertainment
5 miles from Winter Park The American Sirens deliver a luxury boutique concert experience; a dazzling female fronted vintage cabaret that transports you to the golden age of Hollywood glam…
Spring Hill, FL
Jazz Band / 1920s Era Entertainment
73 miles from Winter Park
4 Verified Bookings Sharon W. said “I had this group come out and play at my wedding a few years ago and they did such a great job that today I still think about how we had such a great…”
Tampa, FL
Samba Dancer / 1920s Era Entertainment
82 miles from Winter Park
1 Verified Booking Sepi V. said “Johanna and her Dancers put on an Amazing show for my guests last weekend!! Beautiful costumes and gorgeous dancers, and the way they danced made our…”
Offers Virtual Services
Tampa, FL
Jazz Band / 1920s Era Entertainment
82 miles from Winter Park
81 Verified Bookings Jc said “A guitarist and a base very professional and knowing the full bossa nova repertoire. Feedback from someone who lived 8 years in Rio de Janeiro...”
Tampa, FL
Dance Troupe / 1920s Era Entertainment
82 miles from Winter Park
7 Verified Bookings Alma said “I hired the Show Girls for my husbands 40th Birthday Party as a surprise for him and all my guests. I had never hired any entertainment and did not know…”
In the past year, 1920s Era Entertainers have sent 594 quotes to event planners
1920s Era Entertainers rank #135 in popularity out of 545 categories on GigSalad
498 1920s Era Entertainer reviews on GigSalad with an average rating of 4.9 stars
Birthday Parties and Cocktail Parties in Winter Park
Find your best flapper dress and bust out a Gatsby-esque fedora hat and get ready to swing! Let these great bands travel you back in time to the roaring twenties. An era full of swingin' music, jazz greats, and trying to get around that pesky Prohibition. So what are you planning? A birthday party, anniversary, or themed event? Let one of these fantastic bands, musicians, or singers set the mood and get your guests a swingin'! So quit sitting there tappin' your toes and get to booking one of these great 1920s Era Entertainment acts today! 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.
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