Island City House

A Garden in Old Town That Has Kept Guests Since 1912

William Street runs parallel to the noise rather than through it, and about halfway along it a gate opens onto something Key West has mostly built over: a proper tropical garden, palms and orchids and brick paths, with three white clapboard houses standing around it. Island City House has been taking guests since 1912, which makes it the oldest guest house on the island still in business, and the layout explains the longevity. Nothing here is a corridor. You cross the garden to reach your door, and the pool sits in the middle of it, fenced and shaded, sounding like a courtyard rather than a resort.

Why It Works

Three things decided it for us. The accommodation is entirely suites, most with a full kitchen, a separate living room and a porch, which turns a Key West week into something closer to renting a house with a front desk attached. The position is the good compromise, four blocks from Duval Street and the sunset crowd at Mallory Square, far enough that the evening ends when you close the gate. And the property is genuinely old, not styled to look it, with the lace, the antiques and the ceiling heights that come from being built before air conditioning existed.

Why This Location

411 William Street sits in the residential heart of Old Town, on the harbour side, where the streets are lined with conch houses and the traffic is bicycles. Everything is walkable from here: Mallory Square and the sunset celebration, the Duval bars, the Hemingway Home, the Truman Little White House, the shrimp boats and restaurants along the historic seaport. Bikes can be rented on site, and in Key West that is the correct way to move. The airport is a short drive east, and the road back up the Keys begins at the end of the island.

Fast Facts

• Price: premium, higher in the winter season

• Vibe: historic, leafy, residential, quietly old Key West

• Rooms: a little over twenty suites across three houses, from studios to two bedroom units with full kitchens

• Best For: families needing space, couples on a long stay, travellers who cook

• Our Favorite Thing About the Hotel: the hammocks on the Cigar House king suite porches, hung looking straight at the pool

• Dining: no restaurant on site, kitchens in most suites and the seaport tables a few minutes away on foot

• Amenities: heated garden pool, sauna, in room massage through a local spa, bicycle rental, porches and balconies on almost every suite

• Attractions: Duval Street, Mallory Square, the Hemingway Home, the Historic Seaport

Three Houses, and How to Choose Between Them

The main Island City House holds eleven suites in Victorian island style, lace curtains and antique furniture, studios through two bedrooms, and it is the one to take for the sense of the building. The Arch House, the old carriage entrance, runs Caribbean, with two bedroom suites that have their own dining areas and full kitchens, and studios that open onto the garden. The Cigar House sits at the pool, five one bedroom suites in tropical plantation style, all with separate living rooms and water in view from the porch. Families tend to want the Arch House, couples the Cigar House.

A Garden Built for Sitting Still

The grounds are the reason people come back rather than trying the next place. Mature planting keeps the paths shaded through the middle of the day, the pool is heated for the cooler months and fenced for children, and there is a sauna for the evening. Massage can be booked into the room. It is a small property with no restaurant and no bar, and that absence is deliberate: the garden does the work that a lobby does elsewhere, and by the second morning most guests have chosen a chair.

What a Full Kitchen Changes on This Island

Key West eats out well and expensively. A suite with a kitchen shifts the arithmetic of a week here, letting a family cook breakfast on the porch, keep the shrimp bought at the seaport and come home from Duval without a plan. Combined with the laundry of a long stay and the bicycles at the gate, it is what makes this address a base rather than a stop, and the reason we would send anyone staying five nights or more to William Street first.