1920s Era Musicians & Bands for Hire in Key West

Discover 98 professional 1920s era musicians and bands available for hire in Key West, Monroe County, Florida, United States, with an average rating of 5 out of 5 from 238 reviews from real clients. These local vintage jazz ensembles specialize in authentic 1920s entertainment and Great Gatsby-style performances.

Local booking prices start from $150, with an average cost of $1133 for professional 1920s musicians near you. Many acts offer both traditional jazz standards and modern songs arranged in authentic 1920s style, perfect for themed weddings, corporate events, and private parties.

Rated Excellent (5/5) from 238 reviews of 1920s Era Musicians & Bands
Home > 1920s Era Musicians & Bands > United States > Key West
The World's Loudest Clarinet Player™ Currently recording with Jason Miles.

United States

Naples, Collier County

Available in Key West, Monroe County

2 reviews

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I provide different sized bands - Jazz, blues, Bossa Nova, Latin Jazz and more.

United States

North Miami, Miami-Dade County

Available in Key West, Monroe County

3 reviews Avg. response time: 1 hour

Book from $500 (USD)* - get a quote

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We play the greatest songs of yesterday and today.

United States

Charleston, Charleston County

Available in Key West, Monroe County

4 reviews

Book from $5500 (USD)* - get a quote

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3-15 piece jazz orchestra that plays hits from the swing era!

United States

New Orleans, Orleans Parish

Available in Key West, Monroe County

0 reviews Avg. response time: < 1 hour

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6-15 piece New Orleans brass band that plays modern and traditional music

United States

New Orleans, Orleans Parish

Available in Key West, Monroe County

0 reviews

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Jazz-Swing Gatsby 20's and More Styles from a trio to Big Band

United States

Dallas, Dallas County

Available in Key West, Monroe County

7 reviews

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An Elegant and Classy Jazz Band and More!

United States

Dallas, Dallas County

Available in Key West, Monroe County

3 reviews

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Jazz & swing band of varying size from 4 to 7 members

United States

Dallas, Dallas County

Available in Key West, Monroe County

0 reviews Avg. response time: 1 hour

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10 to 16 piece swing band playing the classics of the 20s to the 40s.

United States

Philadelphia, Philadelphia County

Available in Key West, Monroe County

0 reviews

Book from $3275 (USD)* - get a quote

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Jazz, singer songwriter, swing music, solo/duo/trio/quartet and more!

United States

Horsham, Montgomery County

Available in Key West, Monroe County

0 reviews

Book from $300 (USD)* - get a quote

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Trumpet Performer

United States

New York, United States

Available in Key West, Monroe County

0 reviews

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1920s- 1930s jazz vocal trio. Boswell sisters, Andrew’s sisters, originals

United States

New York, United States

Available in Key West, Monroe County

0 reviews

Book from $1200 (USD)* - get a quote

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A Jazz Soul singer/band available for weddings, parties and corporate events.

United States

Manhattan, New York County

Available in Key West, Monroe County

3 reviews

Book from $300 (USD)* - get a quote

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1920-1940s Traditional Delta Blues music

Canada

St. Catharines, Regional Municipality of Niagara

Available in Key West, Monroe County

0 reviews

Book from $500 (CAD)* - get a quote

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Jazz Quartet featuring vocalist Arron Crook

United States

Milwaukee, Milwaukee County

Available in Key West, Monroe County

4 reviews

Book from $300 (USD)* - get a quote

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    Hire 1920s Era Musicians & Bands in Key West, Monroe County, Florida, United States

    Professional 1920s era musicians and bands in Key West, Monroe County, Florida, United States bring the sophisticated sounds of the jazz age to modern celebrations. These vintage performers specialize in authentic period music, featuring traditional jazz standards, swing rhythms, and the distinctive musical styles that defined the Roaring Twenties.

    Nearby 1920s Entertainment Options

    Jazz ensembles near you typically offer a range of lineup sizes, from intimate piano and vocal duos to full period orchestras complete with brass sections and vintage styling. Many groups provide both traditional 1920s repertoire and contemporary songs reimagined in authentic jazz arrangements, ensuring entertainment that appeals to all guests while maintaining period authenticity.

    Pricing for 1920s Musicians in Your Area

    Rates for 1920s era musicians and bands in Key West range from $150 to $7808, with an average booking cost of $1133. Pricing typically reflects the size of the ensemble, performance duration, and additional services such as period costumes or vintage equipment. Smaller jazz combos represent excellent value for intimate gatherings, while larger orchestras provide spectacular entertainment for major themed celebrations.

    How much does it cost to hire 1920s Era Musicians & Bands available in Key West, Monroe County, Florida, United States?

    $ Low Price
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    $150 (USD)
    $$ Average Price
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    $1133 (USD)
    $$$ High Price
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    $7808 (USD)
    The average price for 1920s Era Musicians & Bands available in Key West, Monroe County, Florida, United States is $1133 (USD). Above you will also find a budget price and high end price. Contact the supplier you like for an accurate quote.

    Frequently asked questions


    Hiring 1920s era musicians & bands is a popular choice for Gatsby and prohibition-themed parties, vintage weddings, corporate dinners and cocktail receptions. The elegant, upbeat style of 1920s music works especially well as both background entertainment and a main performance to get guests dancing.

    Many 1920s era musicians & bands offer the option of performing in 1920s-style attire, such as flapper dresses, pinstripe suits and fedoras. This can add an extra layer of authenticity to themed events. It is worth discussing costume options with the performers when making an enquiry.

    The 1920s era musicians & bands in Key West, Monroe County, Florida, United States specialise in the sounds of the Roaring Twenties, including jazz, swing, Charleston and ragtime. Many performers recreate the authentic feel of a 1920s speakeasy or Gatsby-themed event, often featuring period-appropriate instruments such as banjo, clarinet and trumpet.

    The average price for 1920s era musicians & bands on Gig Heaven is currently $1133, with prices ranging from $150 to $7808. Pricing typically depends on the size of the ensemble, whether the act is a solo performer or a full band. Most acts specialise in jazz age standards, Charleston-style numbers and vintage swing, so listening to profile samples is a good way to compare what each performer offers.

    Yes, either add suppliers to your favourites and contact them all at once, or use the find a supplier wizard.

    Booking 1920s era musicians & bands as early as possible increases the chance of securing their availability on your event date, particularly during busy times of the year. However, many suppliers also accept last minute bookings, and we have successfully arranged performances for clients with just a few hours' notice.

    Contact the supplier you are interested in booking by clicking "Contact Now" on their listing. Discuss your requirements using our messaging system or join a video meeting (like a Zoom-call) to speak face-to-face. Once you are ready to confirm your booking, simply ask the supplier to send you a contract, which you can agree to online, or request amendments. Once you agree to the contract you will be asked to pay a 10% deposit to confirm the booking, with the balance payable directly to the supplier by the due date you've agreed on.

    Please browse our help and support section, or if you can't find what you need you can get in touch.

    Frequently asked questions about 1920s Era Musicians & Bands available in Key West, Monroe County, Florida, United States, how to join and how results are ordered are in the help & FAQs.