Southwinds Motel

I’m in my 70s and have traveled all over the world. This was one of the three worst lodging experiences of my life. The worst was finding a tweaker passed out outside my door in Detroit. Given how expensive this room was, this may have been the worst. The air conditioner was so loud that we only used it during the warmest part of the day. Some USB ports and wall outlets didn’t work, and I found out on the first morning when my phone and tablet hadn’t charged. Part of the shower temperature control disintegrated in my hand. The hotter the water, the lower the pressure, so I had to keep my head within six inches of the showerhead to rinse as water dribbled down my body. The TV switched itself off after two to ten minutes, and I couldn’t keep it on. Staff weren’t friendly or helpful. No one looked up when we entered the lobby, and I had to interrupt their personal conversation to get help. The included breakfast was the second worst I’ve had. It was all poor-quality, prepackaged food. Live music from the bar next door played outdoors until 11 or 12, depending on the night. Even with my hearing aids out and headphones on, I could still hear it. We ran the noisy air conditioner to try to drown out the music. Key West was great. Staying at Southwinds Motel was a nightmare.

The downtown location is ideal, but poor management and hygiene spoiled the stay. The property is quite run down, and cleanliness was a real issue: there was hair in the shower and a previous guest’s toothbrush on the sink. The reception staff were inflexible and seemed purely administrative. After checkout, they didn’t release my $150 deposit even though there were no charges. It took a month to sort out, and the staff were unhelpful during follow-up, blaming my bank and even hanging up on me. I called twice and was given the same false script: that the deposit is released at checkout and the problem was with my bank. My bank said the merchant service hadn’t released it because the checkout process hadn’t been completed properly. I own and manage four businesses in Florida and tried to explain, but both times they put me on hold indefinitely. For breakfast, I’d skip the “free” option and walk a few hundred meters to the local French bakery. It costs money, but the quality is much better.

One star for several reasons. My last stay here wasn’t good, but I considered giving it another try because of the great location and the iconic Tipsy Rooster, which I wanted to share with a friend who’d never been to Key West. We were splitting the trip between three hotels. When we had to reschedule, the other two, which were much nicer, had no problem refunding our deposits. Southwinds kept our deposit under its cancellation policy, which is fair enough, but when I asked if it could be applied to new dates, they said no because the booking was already cancelled. Then they emailed to ask how the stay I never took had been. We won’t rebook. Be aware their cancellation deadline is much earlier than the 72-hour policy many hotels have.

The quiet location and kindness from the moment we arrived made this a really pleasing week at Southwinds. We usually stay on the Gulf end of Key West, but chose the Atlantic side this time for several reasons and couldn’t have been happier. The room could use newer furniture, but the peace and location made up for that. It’s one block from the quieter end of Duval and one block from the Atlantic Ocean. There are two spotless pools, a grab-and-go breakfast, and desk staff available 24 hours a day who are happy to help. Special thanks to the wonderful women in the front office. We highly recommend Southwinds and plan to stay again on future Key West trips.