There are many great options to stay in Key West from historic hotels, B&Bs and beachfront resorts. I prefer staying downtown so you can walk to bars and restaurants. My recommendations include:
Marquesa Hotel, 600 Fleming St.: Built in 1884, this is an historic hotel a few blocks from Duval St. with beautifully restored rooms, a lovely pool and well-regarded restaurant.
The Inn on Fleming (formerly The Artist House on Fleming:) I was so pleased with my choice of this Bed & Breakfast at 1016 Fleming, a few blocks from Duval St. I liked walking around the surrounding neighborhood away from the throngs of tourists. From here it was an easy walk to all of the restaurants, shopping and historical sites. I never got in my car in three days! My room on the second floor, The Truman Room, was large and attractive with a queen bed. The bathroom however, was somewhat small. Downstairs, there was a nice living room and outdoor terrace with a small pool. The spacious kitchen was set up every morning as a self-service breakfast buffet with many items to choose from. The fruit, cereal and fresh breads and pastries were great. The owners and staff were excellent and most accommodating in sharing their ideas as to what to see in town and where to eat! They have a sister property, The Artist House Circa 1890, that you should check out if the Fleming property is booked. As a guest, you can have cocktails at Eaton St. in the afternoon.
Southernmost Beach Resort: When I had dinner on the beach in their restaurant, I really liked this beachfront hotel. I would definitely consider staying here next time, due to the great beach location. It is at the opposite end of Duval St., away from the cruise ships.
Other hotels and resorts getting excellent reviews include:
The Marker Waterfront Resort: This is a 96-room resort in the heart of Key West’s Old Town that opened in 2014. The rooms look beautiful and I hope to stay there on my next visit.
Nearby the Pier House Resort & Spa is also recommended. It has two, restaurants, spa, three bars and 142 rooms. Chicago friends were just there and really enjoyed it.
Thanks to the NY times, I read about the H2O Suites Hotel, It is an adults only resort opened in 2017 in the Historic District, with 22 suites, 11 with plunge pools plus rooftop pool and bar.
If you want to stay outside of the Old Town, then you might enjoy The Gates Hotel Key West, The Perry Hotel Key West at the Stock Island Marina with three waterfront restaurants and the Oceans Edge Resort & Marina with ocean views from all accommodations. Sunset Key Cottages has one, two, three and four bedroom cottages for rent along with bar, restaurant and spa.
I recently read a review on a new property that has opened in Key West, the Barbary Beach House Key West. It is a contemporary, ocean front property with 184 guestrooms with soft neutrals and warm rattan accents to ocean and garden views. It looks like a really lovely property.
Chicago friends just returned from Key West and recommended The Gardens Hotel. They really enjoyed the location as well as the pool, grounds, patios and courtyards during their stay. 526 Angela St.
Recently opened is The Saint Hotel Key West, an Autograph Collection hotel at 417 Eaton St. is also recommended as is the Kimpton Key West which contains five properties and bungalows throughout the Historic District. I will definitely stay there on my next trip.