Key West’s idyllic setting at the end of a sun-soaked archipelago has been drawing visitors long before Ernest Hemingway likened the island to St. Tropez. Demand for hotel rooms has only increased since then, and limited space means only so many places to lay your head. Bankrolling your stay in the Southernmost City may cost more than you anticipated, but what price can you really put on paradise?
Old Town is the most sought-after location for lodging with its historic B&Bs on shady side streets. It’s also home to Duval Street where you’ll find many of the boutiques, restaurants and late-night bars. One of the perks of staying here: you can park your car and walk to most places. Bookending the bustling thoroughfare, upscale properties like Ocean Key Resort and Spa and Southernmost Beach Resort offer waterfront views, sandy shores and luxury amenities. For the ultimate getaway, take the ferry across the Key West Harbor to Sunset Key where you can relax in a waterfront cottage on a private island. Outside of Old Town, you’ll find more competitive pricing at accommodations like The Gates, a new boutique hotel. While you might be able to show up and find a hotel last-minute, it’s not recommended. Festivals, weddings and holidays often leave every room on the island booked. You’d have to travel back up the Keys, possibly to Miami in search of a place to stay. So make your reservations early; you might even luck into a special discount.