Little Pearl

Casual cafe offering breakfast, sandwiches, coffee, and other classic Cuban eats, plus live music.

Laid-back lodging offering rooms in a historic house or garden cottages, plus a waterfall pool. Set across private cottages and a 2-story conch-style house dating from the late 1800s, this all-adult B&B is tucked away on a street known for its nightlife, and is a 2-minute walk from the Ernest Hemingway House. Brightly decorated, low-key accommodations range from 6 rooms in the main house, to a few garden cottages. All feature flat-screens with cable channels, free Wi-Fi and minifridges; some have private balconies or patios There's a suite with a porch swing, and some cottages add whirlpools and kitchens. Amenities include expanded continental breakfast with an emphasis on organic food, and a garden with a waterfall pool and a hot tub.

Nestled on the Gulf of Mexico, this tropical retreat boasts lush landscaping, four inviting pools, welcoming staff, and cozy rooms with garden or water views.

Cozy, romantic spot serving French-Caribbean fare, signature hog snapper & a broad wine list.

A quirky dive bar in Key West, Bobby's Monkey Bar boasts karaoke, a cash-only policy, and friendly vibes that keep both locals and tourists coming back.

"Hemingway Distillery is home to the makers of Papa’s Pilar Rum and nestled in the heart of Key West, just yards from where Ernest Hemingway used to dock his boat. Inspired by Hemingway’s adventurous spirit, the distillery offers tours, cocktail classes, and other special experiences. Visitors can explore the gift shop, featuring Papa’s Pilar Rum and Hemingway Whiskey. Experience the artistry behind these hand-crafted sister brands."

Charming tapas bar pairing global small plates with house-specialty sangria in a warm room.

Nestled in Key West, this serene Victorian hotel boasts elegant rooms, lush gardens, two pools, and a top-notch restaurant for a luxurious retreat.

Posh chain serving American fare, including brunch & dessert. Some offer dinner & cocktails.