The Grand Guesthouse

The Grand Guesthouse was built in the 1880s as a home for cigar manufacturer workers, and has since been converted to a single-family home, and then a rooming house. These days, the property tends to appeal to couples on Key West getaways, and those who want a quiet atmosphere within close proximity of Duval Street and the beach. With its lush, tropical landscaping, front porch with wicker chairs, and kitschy touches like pink flamingos and metal iguanas, the property has a low-key, romantic charm. Inside, despite being a bit cramped, the office is lovely and welcoming with wood floors, warm yellow walls, a leaf-shaped ceiling fan, tourism brochures, and framed photography -- these are the kind of personalized details that lend the property a unique appeal. Railings and fences are painted bright white, setting off the abundant natural foliage, while a worn wooden walkway winds around the cottage to the breakfast terrace. Here, guests can dine on wooden lounge chairs with blue-and-yellow-striped cushions. There’s also a hammock in the garden.

This guesthouse is in a quiet neighborhood, and about a half-mile from livelier Duval Street, with plenty of bars and restaurants. South Beach is a 10- to 15-minute walk, while the Ernest Hemingway Home and Key West Lighthouse are about 15 minutes' walk. It's about a five-minute drive to Truman Little White House, Key West Aquarium, and the Sunset Celebration at Mallory Square. Key West Bight Ferry Terminal takes five minutes by car. The Key West International Airport is a 10-minute drive.

Interior decor is modest and beachy, and quite cozy thanks to breezy ceiling fans and wood-paneled walls, some painted pale blue. Local artwork and kitschy tropical touches, like iguana and toucan wall hangings, enhance the views of leafy plants visible through guest rooms windows. Each room is air-conditioned and has a mini-fridge, TV with cable channels, iPod docking station and CD player, and free Wi-Fi; suites have kitchenettes with sinks, microwaves, and coffeemakers, and separate dining and living areas, some with vintage couches. Bathrooms have shower/tub combos, eco-friendly products, and hairdryers. Beach towels are available on request. All rooms have outdoor seating areas. 

The free, daily breakfast buffet is quite extensive and served outside on the wood patio; items include hard-boiled eggs, bagels and English muffins, a sweets tray, fruit, yogurt, coffee, tea, and orange juice. At the entrance to the guesthouse is a gravel parking lot that’s free for guests. Red bicycles are parked in the garden and available to rent for a fee. Luggage storage is also offered at no additional charge. The staff provides concierge services, recommending restaurants, water-sports activities, and shopping, and sometimes offering coupons. Business services, including printing and copying, can also be requested.