The Mermaid & The Alligator

A White Picket Fence, Three Blocks Off Duval

Truman Avenue carries traffic, and the house behind the white picket fence does not appear to notice. The Mermaid and The Alligator occupies a Victorian estate of 1904, verandas on two levels with hammocks slung along them, and a tropical garden at the back that has been allowed to grow into something closer to a canopy than a courtyard. Nine rooms is the entire inventory. Breakfast happens outside beside a plunge pool, a wine hour happens in the pavilion at dusk, and the owners' dogs move between the two. Key West has hundreds of places to sleep. This is one of the few that behaves like a house.

Why It Works

Old Town guesthouses are the island's signature, and many of them trade on the architecture alone. This one does the architecture and then adds the garden, which is what separates a pretty house from a place worth three nights. The adults-only rule, set at sixteen, keeps the register calm. Nine rooms means the innkeepers know who is in each of them. And the position, three blocks back from Duval, hands you the whole of Old Town on foot while leaving the noise at a distance you choose. There is no restaurant, which in a town this dense is not a loss.

Why This Location

Truman Avenue runs through the heart of Old Town, and three blocks is the right distance from Duval Street: near enough to walk to dinner and back without a plan, far enough that the evening does not arrive through the window. The Hemingway Home and the lighthouse are a short walk south. Mallory Square, the harbour and the sunset crowd are north. Smathers Beach and the Atlantic are a bicycle ride east, and the house keeps beach equipment for exactly that. Self-parking on site solves the island's hardest practical problem.

Fast Facts

• Price: Premium

• Vibe: 1904 Victorian, garden-shaded, adults only

• Rooms: Nine, each decorated individually, several with veranda access

• Best For: Couples, quiet weeks, travellers who want Old Town on foot

• Our Favorite Thing About the Hotel: Breakfast served in the garden beside the plunge pool

• Dining: Full breakfast daily with homemade muffins and a hot dish, an evening wine hour in the garden pavilion, and the Duval Street kitchens three blocks away

• Amenities: Tropical garden, plunge pool, hot tub, verandas and hammocks, beach equipment, concierge, self-parking on site, resident dogs

• Attractions: Duval Street (three blocks), the Hemingway Home, the Key West Lighthouse, Mallory Square at sunset, Smathers Beach

The Garden, the Plunge Pool and the Wine Hour

The garden is the reason to book. It has been planted densely enough to hold shade through the middle of the day, with lounging areas set among it and a plunge pool at the centre. Breakfast is served out here, a hot dish of the day alongside homemade muffins, and the morning tends to start slowly as a result. At dusk the pavilion takes over for a wine hour, which is where guests meet one another and where the recommendations that matter get passed around. The dogs attend both sittings.

Nine Rooms, No Two the Same

Each room has been decorated on its own terms rather than to a house standard. The Caribbean Queen gives the idea: a four-poster king bed, bold colour, and a veranda with a hammock on it. Some rooms open onto the verandas, others onto the garden, and the difference is worth a conversation at the time of booking rather than a guess. Hammocks, towels and beach equipment are provided, as is self-parking. What is not provided is lunch or dinner, and in Old Town that is no hardship at all.

Practicalities for an Old Town Stay

Check-in opens mid-afternoon and check-out is late morning. The adults-only policy excludes under-sixteens, so this is not a family address. Dogs live on the property, a delight for most guests and worth knowing for anyone who would rather it were otherwise. Winter and early spring are high season on the island and fill first, while the shoulder weeks either side give you the same garden with fewer people in it. Nine rooms go quickly, so book further ahead than you would for a larger house.