Kimpton Ella's Cottages, an IHG Hotel

Cigar Makers Houses, and the Woman They Are Named For

Simonton Street runs one block back from Duval, and the difference between the two is the difference between a night out and a night’s sleep. This corner of it was cigar country: the houses were built for the workers who rolled Havana leaf in Key West, and the largest of them later belonged to a steamboat captain, Pete Hanlon, and to his wife Ella, whose hospitality the property still borrows its name from. What survives is a small compound of clapboard buildings, porches, shutters and a pool in the middle, restored rather than rebuilt.

Why It Works

Because it is a genuine collection of old Key West houses run with the standards of a modern hotel. Twenty two rooms means the staff learn your name in a day; the Kimpton operation behind it means the beds, the concierge and the dog policy all work. The rituals do the rest: breakfast at the poolside lounge in the morning, a glass of rose poured every afternoon at three, coffee and water all day. It is a couples address, quiet by design, and it sits a two minute walk from the noise without being in it.

Why This Location

811 Simonton is in the historic heart of Old Town, one street off Duval and a short walk from the Bahama Village end of the neighbourhood, where the restaurants get better and the crowds thin. Everything worth seeing is on foot: the Hemingway Home, the lighthouse, the Historic Seaport, Mallory Square for the sunset, the beaches at the southern end of the island. Bicycles, e bikes and scooters can be arranged through a local rental partner at preferred rates, and on this island that is the right way to travel. Limited parking is available on site for anyone arriving by car.

Fast Facts

• Price: premium to luxury, highest in the winter season

• Vibe: historic, romantic, low key, grown up

• Rooms: 22 rooms and suites spread across restored conch cottages

• Best For: couples, honeymoons, travellers with a dog, anyone who wants Old Town on foot

• Our Favorite Thing About the Hotel: the rose poured by the pool at three, which turns strangers into a small crowd by the second afternoon

• Dining: complimentary continental breakfast at the poolside lounge, coffee and tea through the day, with the Duval and Bahama Village kitchens a short walk away

• Amenities: pool, poolside lounge, concierge, dogs welcome, yoga mats and filtered water in the rooms, bicycle and scooter hire arranged, limited on site parking

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

Rooms Inside Old Conch Houses

The accommodation is spread across several buildings rather than gathered in one, which is what gives the place its texture. Expect high ceilings, timber floors, shutters and a porch or a balcony on most units, with the modern comforts installed discreetly rather than announced. Sizes vary from compact doubles to suites, and the ones facing the garden and pool are the quieter choice. Nothing is standardised, and that is the point: two guests comparing notes at the pool will not have stayed in the same room.

The Pool, the Breakfast and the Rose at Three

The centre of the property is the pool, shaded on one side by the lounge where breakfast is laid out in the morning between eight and ten. In the afternoon the same lounge pours a complimentary glass of rose, an hour that does more for the atmosphere of a small hotel than any amount of design. Coffee, tea and filtered water are available through the day. There is no restaurant, and there does not need to be: some of the best kitchens in Key West are within a few minutes on foot.

Getting Around Without a Car

Old Town is flat, small and hostile to drivers, which makes a hotel this central worth more than its square footage. Duval is one block away, the seaport and Mallory Square a ten minute walk, the beaches and the Southernmost Point a pleasant ride. The concierge arranges bicycles, e bikes, scooters or a golf cart through a local partner, and the honest advice for most guests is to leave the car in the lot for the length of the stay.