When Steve and I were looking for a place to stay on Key West, the options seemed overwhelming! We ended up booking a beautiful, historic bed and breakfast through Hotels.com entirely on points, and despite COVID regulations, we were glad we stayed where we did. Here’s our experience staying at the Southernmost House in Key West.
My ideal situation: Everything I Want in a B&B
The Southernmost House Hotel is, predictably, on the south side of the island of Key West. It’s close to restaurants and a beautiful place to watch the sunset (and less crowded than Mallory Square), and right at the end of Duvall Street, which is the main drag through Key West. We were within walking distance from pretty much everything we wanted to see and do, without being in the thick of the noise and activity the whole time!
Many of the rooms have ocean views as well, which is not the case for most accommodations on Key West. Oh, and we were just a block away from the Southernmost Point for a photo-op!
Keep reading: The 10 Best Things to Do in Key West
The Southernmost House property boasts a pool, a restaurant called the seaside cafe at the mansion, oceanfront lounging, and bunnies! There are two bunnies that live at the mansion, and morning is the best time to see them hopping around.
More here: What to Know Before You Visit Key West
We stayed in room 101, which is not in the main house, but is a separate bungalow. This was the best room on the property because of its privacy and spaciousness. We also had the added benefit of an entire concrete platform outside our room, right next to the ocean. It was the perfect workout spot, sunrise viewpoint, and sunset spot, too!
We had our own kitchenette, sectional couch, table and two chairs, bench, and a smarTV as well. The bed was king-sized, which is too big for us, but we weren’t complaining! We even had a little table and chairs outside so we could enjoy the warmth of the sun and the sea air as much as possible.
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The bathroom was just as spacious as the bungalow itself. Surprisingly, the towels were super soft–not something a lot of hotels or B&Bs seem to achieve. The bathtub drained slowly, but that was our only issue. The rest was great!
The breakfast was… weak. Maybe it’s just because of COVID, but gnerally, I think they could have done better. Other restaurants were open, so a bed and breakfast could have been, too. We appreciated the options, but the one day we had breakfast here instead of out at a restaurant, we were both hungry again by 10:00am!
Read next: The Best Food to Eat in Key West
The history was the real reason we booked this place! You know I’m a sucker for unique history and architecture. This Queen Anne-style mansion was built in 1896 for a judge and his wife, who happened to be the daughter of one of Florida’s first millionaires. Would you believe they built this grand mansion as a one bedroom home? Since then, it’s been a speakeasy, casino, a cafe, and even a Cuban-style nightclub!
It’s now an 18-room bed and breakfast, including the bungalows, and it boasts an impressive roster of famous guests. During its prohibition speakeasy heyday, Gore Vidal, Truman Capote, Louis Armstrong, Gloria Swanson, Tallulah Bankhead, and local legend Ernest Hemingway all came to socialize and probably imbibe.
Since becoming a private residence again in the 1950s, five presidents have stayed here over the years: Presidents Truman, Eisenhower, Kennedy, Nixon, and Carter. Not only that, King Juan Carlos of Spain stayed here on a visit to Key West as well! Its pastel color scheme and beautifully maintained architecture have made it a hot spot for weddings and special events for many over the years, including us celebrating our return to travel!
Want more? Check out my United States Page for everything I have on Key West and Florida!
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