Events
Racing
September 11 to 13, 2026
Fort Myers Beach
High-speed offshore powerboat racing brings a full weekend of practice runs, qualifying races, live entertainment, and the championship race along the Gulf.
Festival
September 18 to 27, 2026
Captiva, Cape Coral, Downtown Fort Myers, and Fort Myers Beach
More than 60 live performances are spread across the region, with the Fort Myers Beach portion taking place from September 25 to 27.
Parade
November 7, 2026 · 5:30 to 8:00 p.m.
Estero Boulevard and Bayside Park, Fort Myers Beach
A family-friendly nighttime parade with illuminated floats, costumes, lanterns, and glowing displays along the beach.
Beach Event
November 19 to 23, 2026 · 10:00 a.m. to 5:00 p.m.
DiamondHead Beach Resort, Fort Myers Beach
Professional artists create large, detailed sculptures from beach sand with demonstrations, photo opportunities, and an amateur contest.
Holiday
December 5, 2026
Back Bay and surrounding waterways, Fort Myers Beach
Decorated boats light up the waterways with holiday cheer, drawing a festive crowd from nearby waterfront restaurants and public viewing areas.
Holiday
December 31, 2026
Times Square and Downtown District, Fort Myers Beach
The island typically celebrates with live music, waterfront festivities, and a midnight countdown around the Downtown District.
Music
Year-round
Fort Myers Beach restaurants and outdoor venues
Local restaurants and outdoor venues host live music throughout the year, with schedules changing based on season and weather.
Music
Select Fridays and Sundays
Bayside Park, Fort Myers Beach
Free waterfront concerts feature local bands and a relaxed island atmosphere, with lawn chairs encouraged and schedules subject to weather.
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Check your dates below — we typically reply within one business day. 7-night minimum stay.
Sleeps 4 · Small-dog friendly with approval · Direct beach access · Heated pool