Clearwater Jazz Holiday
Four nights of world-class music on the downtown waterfront, minutes from the beach. One of Florida's longest-running music festivals returns to Coachman Park every October.
Nearly five decades of jazz by the bay
Since 1980, the Clearwater Jazz Holiday has closed out October with a waterfront festival that has grown from a local jam into a nationally known, multi-night event. Today it fills Coachman Park and The Sound, Clearwater's stunning bayfront amphitheater, with acts spanning jazz, funk, soul, blues, and headline crossover artists, plus free festival experiences alongside the ticketed shows.
For visitors it is the perfect excuse for a fall beach trip: October brings some of the year's best value on rentals, the summer humidity is gone, the Gulf is still warm, and the music is a ten-minute hop from the sand.
Big-name lineups
Four nights of national headliners and rising stars on the bayfront stage at The Sound.
Free & ticketed
Paid admission gets you close to the stage, while free festival experiences keep the whole weekend open to everyone.
Value-season timing
October rentals run roughly a third below spring peak rates, so the trip costs less than the tickets suggest.
Beach by day
Mornings on the sand, music at night. The park is minutes from Clearwater Beach by trolley or car.
Making a festival weekend of it
- Stay on Clearwater Beach or Island Estates. You get the beach all day and a short ride to Coachman Park each evening. Downtown fills up; the beach side sleeps better.
- Skip the parking scramble. The Jolley Trolley connects the beach to downtown, and our parking guide covers the garages if you drive. Leave extra time on headliner nights.
- Book the rental before the lineup drops. Festival weekend is the busiest stretch of Clearwater's October. When the artists are announced, the closest homes go within days.
- Bring a light layer. Mid-October evenings by the bay are the first genuinely pleasant nights of fall, usually low 70s by the encore.
- Check what else is on. Stone crab season opens the same week and our events calendar lists everything happening around your dates.
Stay for the encore
Tell us your festival dates and headcount. October is value season, so a beach rental for the whole long weekend costs less than you would guess.
Browse rentals See October ratesFrequently asked questions
When is the Clearwater Jazz Holiday?
The festival returns to Coachman Park every October. The 47th edition runs October 15 to 18, 2026. Lineup announcements and tickets are handled by the festival at clearwaterjazz.com.
Where is the festival held?
At Coachman Park and The Sound amphitheater on downtown Clearwater's bayfront, one of Florida's best outdoor venues, about ten minutes from Clearwater Beach.
Is the Clearwater Jazz Holiday free?
Both. The festival pairs ticketed admission near the stage with free festival experiences, so there is a way in at every budget. Check the current year's structure when tickets go on sale.
Where should I stay for the Jazz Holiday?
Clearwater Beach and Island Estates are the sweet spot: beach days, an easy trolley or drive to the park at night, and quieter sleep than downtown on festival weekend. Book before the lineup announcement for the best pick.
Is October a good time to visit Clearwater anyway?
One of the best. Rates run roughly a third below the March peak, the humidity breaks, the Gulf is still around 79 degrees, and the crowds are the year's thinnest. The festival is the cherry on top.
Music on the bay, beach out your door
With 92 rentals across the Gulf beaches, your festival weekend comes with sand between the sets.
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