Boutique, Beachfront or B&B? Key West's Top 10 Hotels Embody Island Charm

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.



This new boutique hotel at the entrance to Key West has partnered with local businesses, artists and designers to capture the unique character of the island. Their Rum Row bar features handcrafted cocktails made with Key West First Legal Rum...  Read More



The Pier House has all the ingredients for a perfect Key West vacation: waterfront views, private sandy beach, variety of dining options, award-winning spa and prime location near Mallory Square. Their 119 waterfront guestrooms and 23 expansive...  Read More



Just one block away from Duval Street and the beach, Santa Maria Suites is a great alternative to a rental home with the added amenities of a luxury hotel. Perfect for those traveling with families or a large group, all of the 35 spacious one-...  Read More



This elegant boutique hotel boasts a large private natural-sand beach and a picturesque pier with a gazebo extending over the Atlantic. A Waldorf Astoria Resort, The Reach combines a casual atmosphere with top-notch customer service and...  Read More



The premier guesthouse for gay and lesbian couples, this 17-room inn is does everything right from the shaded pool and Jacuzzi to expanded continental breakfast and clothing-optional sundeck. In the heart of Old Town, this lovingly restored Key...  Read More



A cross between an inn and B&B, this gem is hidden in plain sight at Old Town's busiest intersection--Truman Avenue and Duval Street. Verdant gardens, tranquil waterfall and a privacy wall ensure that while all the action is just steps away, the...  Read More



On the less-crowded end of quirky Duval Street, rests Southernmost Beach Resort, an upscale (yet unpretentious) hotel. It boasts a private pier, sandy beach dotted with hammocks, oceanfront pool, Shores Bar and on-site restaurant. The rooms...  Read More



Just three blocks from Duval Street, this charming adults-only B&B is tucked away in a lovingly restored Victorian home. The owners strive to make guests feel like they are staying at a good friend's home. The decor is an eclectic mix of art...  Read More



For the ultimate getaway, board the ferry in Key West for a quick cruise to Sunset Key, a secluded 27-acre island. Dotted with 40 two-, three- and four-bedroom cottages, this recent addition to the Luxury Collection is laced with footpaths...  Read More



Conveniently nestled between Key West Harbor and Mallory Square, Ocean Key Resort & Spa is the epitome of barefoot elegance. Their spacious rooms and suites offer understated tropical decor and luxurious comfort like whirlpool tubs and their...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia