Key West is consistently ranked as one of the most expensive vacation destinations in Florida and the United States. In 2026, a mid-range traveler can expect to spend between $280 and $350 per day, while luxury budgets often exceed $700 to $900 per day. The primary driver of these costs is accommodation; due to the island's limited land area and high demand, even basic hotel rooms often start around $200–$300 per night during the peak winter season (December–April). Dining and activities also carry a premium, with a standard dinner for two at a mid-range restaurant typically costing $60–$120. To save money, experts recommend visiting during the "shoulder seasons" of May–June or November, where lodging prices can drop by 25–35%. Additionally, flying into Miami or Fort Lauderdale and driving down the Overseas Highway can often save hundreds of dollars compared to flying directly into Key West International Airport (EYW).