Kimpton Lighthouse Hotel, an IHG Hotel

Across the Street From the Lighthouse, a Block Off the Noise

Whitehead Street runs parallel to Duval, one block west and several decibels quieter, and it carries most of what people actually come to Key West to see. At number 902 the hotel faces the white tower of the Key West Lighthouse and its keeper’s quarters; the Hemingway Home stands almost opposite. The buildings themselves are restored houses from the mid-1800s, timber and shutters and deep verandas, gathered around a pool in the middle of the block. Forty-five rooms, no lobby to speak of, and a front desk that behaves more like a household. It is the oldest part of the island, lived in rather than preserved.

Why It Works

The location did most of the convincing. Guests wake up inside the postcard, walk to the lighthouse, the Hemingway Home and the cemetery before the tour buses arrive, and are still two minutes from Duval when they want it. What sealed it is the scale: a handful of restored houses rather than a block, a pool at the centre of them, and a daily rhythm of breakfast, afternoon drinks and a bar that locals use. Old Town has larger hotels. Very few put you this close to everything while still feeling residential.

Why This Location

This is the heart of Old Town, and the geography is walkable to the point of making a car pointless. The Hemingway Home and the Key West Lighthouse and Keeper’s Quarters are across the street. The Key West Cemetery, the Southernmost Point and the Duval bars are each a short walk in different directions, and Mallory Square with its sunset crowd is about fifteen minutes north on foot. Whitehead itself is a quiet street of clapboard houses and shade, which is the real reason to sleep here rather than one block east: the centre, without the noise that usually comes with it.

Fast Facts

• Price: €€€

• Vibe: Historic, low-slung, sociable around the pool

• Rooms: Forty-five across several restored mid-1800s houses, including the Hemingway King Suite

• Best For: Couples, first-time visitors who want Old Town on foot, travellers with a dog

• Our Favorite Thing About the Hotel: The view from the front of the property straight onto the lighthouse tower, best at dusk when the street empties

• Dining: Isabel’s Restaurant and Bar, named after Hemingway’s seamstress, with poolside breakfast and an all-day menu built around its mojito

• Amenities: Central pool with poolside dining, daily happy hour, welcome cocktail on arrival, live music, pets welcome

• Attractions: Key West Lighthouse and Keeper’s Quarters and the Ernest Hemingway Home, both across the street; Duval Street one block east; Key West Cemetery and the Southernmost Point a short walk; Mallory Square about fifteen minutes on foot

Rooms Inside Restored Houses, Not a Block

The room stock is spread through several buildings, which means the experience varies more than a category name suggests. Some rooms open onto verandas, some onto the pool deck, some onto the garden paths between the houses. The Hemingway King Suite is the largest and the one built for people who intend to entertain rather than simply sleep. Ask where the room sits in relation to the pool when you book: proximity is charming at breakfast and less so at happy hour, and the property is small enough that the staff will know exactly what you mean.

Isabel’s, the Pool Deck and the Five O’Clock Habit

Isabel’s runs from the morning through the late afternoon, serving breakfast beside the pool and an all-day menu after it, with a mojito that has become the house signature. Happy hour lands at the end of the day and is the moment the hotel is most itself, guests and a few locals on the deck, live music some evenings, the lighthouse going pale above the palms. Dinner happens elsewhere, which is the correct arrangement in a town with this many kitchens within walking distance.

Before You Book

This is a hotel for people who intend to walk. Parking in this part of Old Town is genuinely difficult and the point of the address is that you will not need a car. Dogs are welcome, worth flagging at reservation. The property has long been one of the island’s openly LGBTQ+ welcoming hotels and still carries that atmosphere. If the lighthouse matters to you, ask for a room facing the street.