Andrew's Inn & Garden Cottages

Andrews Inn sits on a quiet lane in Old Town Key West, close enough to Duval Street to walk home from dinner and tucked far enough off it to sleep. The Hemingway Home and Museum is the next-door neighbor, which is not a figure of speech here. One room opens onto a secluded deck beside the Hemingway property and another looks out over his pool and gardens from a private deck upstairs.

There are six guest rooms, each named for a city and each decorated differently: Madrid with cathedral ceilings and an ornamental fireplace, Malaga with its hidden deck, Pamplona under vaulted ceilings a flight up, Roma with a four-poster bed and a front porch in a home dating to around 1900, Paris with handmade Indonesian boat-wood furniture and a French window over the pool, and Venezia with French doors that open onto a deck built for breakfast. Every room has its own bathroom, individually controlled air conditioning and a ceiling fan, Wi-Fi, a smart TV, and a mini refrigerator. Traveling with a group or a wedding party can book the entire inn, all six bedrooms and six bathrooms.

Mornings start with a complimentary breakfast served in the garden between 8 and 10. Afternoons end at the pool, where the daily happy hour has been running long enough to become its own tradition and where most of the repeat guests meet each other. In between, help yourself to the free bicycles, the 24 hour coffee station, the ice and water, and the beach towels, bags and sunscreen by the door.

The inn earned a Tripadvisor Travelers’ Choice award in 2026. Check in starts at 3:00 pm and check out is at 11:00 am, with luggage storage for early arrivals and after hours instructions if your flight lands late. Guests must be 21 to check in and the house is set up with adults in mind, though guests over 14 are welcome. Rooms are non smoking, pets cannot be accommodated, and service animals are always welcome. Parking is limited and reserved in advance, so call ahead if you are driving down.