For a winter retreat in 2026, the best place to stay in Florida depends on your climate preference and activity level. If you want guaranteed warmth (highs in the 70s and 80s), the Florida Keys and Miami/Miami Beach are the premier choices, as they are the only truly "tropical" zones in the continental U.S. during January and February. For a more relaxed, "Old Florida" feel with world-class sunsets, the Gulf Coast—specifically Sarasota, Naples, or Sanibel Island—is highly recommended, though water temperatures can be a bit chilly for swimming without a wetsuit. For those seeking family-friendly entertainment, Orlando remains the heart of winter travel, featuring cooler, comfortable weather for theme park walking. In 2026, the Space Coast (Cocoa Beach/Melbourne) has also surged in popularity due to increased rocket launch activity. Each region offers a distinct winter experience, from the high-energy luxury of the Atlantic coast to the quiet, manatee-watching springs of Central Florida.