The honest answer: when the right property is available and you are prepared. Scarce properties, true waterfront, protected views, rare floor plans, do not wait for a convenient season. When one surfaces, the prepared buyer wins it.
That said, the market has rhythms. Winter brings the most activity, the most inventory, and the most competition. Summer brings fewer buyers, and sellers who list in the off-season are often the motivated ones. Watching a property's time on market and price history tells you more about a specific seller's position than any calendar rule.
The practical move is to be ready before the property appears: financing or proof of funds arranged, criteria defined, and an agent watching the market for you daily. Rangely sets that up for buyers across Miami-Dade and Broward so the timing question answers itself.