Key West Holiday Fest
Date(s): Nov 26–Dec 31, 2026Venue: Key West Holiday FestCategory: Holiday FestivalWebsite: https://keywestholidayfest.com/
25 events found.
Events
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Hemingway in a Funny Way
Weekly Friday comedy-history show. Date(s): Nov 27, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
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Black Friday Market: Shopping Extravaganza
Date(s): Nov 28, 2026Venue: Key West Artisan MarketCategory: Market / ShoppingPhone: 305-731-3385Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/black-friday-market-shopping-extravaganza
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Burgers & Buffet Tunes
Weekly Thursday tribute lunch show. Date(s): Dec 3, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west
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Key West Farmers Market at Truman Waterfront
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Dec 3, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
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Hemingway in a Funny Way
Weekly Friday comedy-history show. Date(s): Dec 4, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
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Pet Pictures with Santa
Date(s): Dec 4, 2026Venue: All Animal Clinic / Key West Holiday FestCategory: Holiday / FamilyWebsite: https://keywestholidayfest.com/
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Holiday Historic Inn Tours
Date(s): Dec 5, 2026Venue: Historic Inns / Key West Holiday FestCategory: Holiday / TourWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/holidays-in-the-keys
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Wesley House Family Services Holiday Village & BeLighted Bike Ride
Date(s): Dec 5, 2026Venue: Wesley House Family ServicesCategory: Holiday / FamilyPhone: 305-809-5000Website: https://keywestholidayfest.com/
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Key West Hometown Holiday Parade
Date(s): Dec 6, 2026Venue: Key West Holiday FestCategory: Holiday / ParadeWebsite: https://keywestholidayfest.com/
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Eaton Street Christmas Stroll
Date(s): Dec 7, 2026Venue: The Studios of Key WestCategory: Holiday / ArtsPhone: 305-296-0458Website: https://tskw.org/eaton-street-christmas-stroll/
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Old Town Trolley Holiday Sights & Festive Nights Tours
Date(s): Dec 8–23, 2026Venue: Old Town TrolleyCategory: Holiday / TourPhone: 855-623-8289Website: https://www.trolleytours.com/key-west/christmas-holiday-tours
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Burgers & Buffet Tunes
Weekly Thursday tribute lunch show. Date(s): Dec 10, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west
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Key West Farmers Market at Truman Waterfront
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Dec 10, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
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Hemingway in a Funny Way
Weekly Friday comedy-history show. Date(s): Dec 11, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
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Holiday Historic Inn Tours
Date(s): Dec 12, 2026Venue: Historic Inns / Key West Holiday FestCategory: Holiday / TourWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/holidays-in-the-keys
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Key West Art & Historical Society Holiday Concert & Bazaar
Date(s): Dec 12, 2026Venue: Key West Art & Historical SocietyCategory: Holiday / Arts MarketPhone: 305-295-6616Website: https://www.kwahs.org/bazaar
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Burgers & Buffet Tunes
Weekly Thursday tribute lunch show. Date(s): Dec 17, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west
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Key West Farmers Market at Truman Waterfront
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Dec 17, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
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Hemingway in a Funny Way
Weekly Friday comedy-history show. Date(s): Dec 18, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
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Burgers & Buffet Tunes
Weekly Thursday tribute lunch show. Date(s): Dec 24, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west
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Hemingway in a Funny Way
Weekly Friday comedy-history show. Date(s): Dec 25, 2026Venue: Comedy Key WestCategory: Comedy / HistoryPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/hemingway-in-a-funny-way-at-comedy-key-west
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Burgers & Buffet Tunes
Weekly Thursday tribute lunch show. Date(s): Dec 31, 2026Venue: Comedy Key WestCategory: Music / Lunch ShowPhone: 305-985-7370Website: https://visitfloridakeys.com/plan-your-trip/plan-book/events/burgers-buffet-tunes-a-tribute-show-at-comedy-key-west
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Key West Farmers Market at Truman Waterfront
Recurring market date listed on Marketspread schedule for the Truman Waterfront market. Date(s): Dec 31, 2026Venue: Key West Artisan MarketCategory: Market / ArtisanPhone: 305-731-3385Website: https://keysartisanmarket.com/farmersmarket.htm
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New Year’s Eve Red Shoe Drop
Date(s): Dec 31, 2026Venue: Bourbon St. PubCategory: Holiday / New Year's EveWebsite: https://visitfloridakeys.com/plan-your-trip/plan-book/events/red-shoe-drop