We pre-booked Southwinds because of the difficulty in finding rooms in Key West at the last minute, even out of high season; and we were influenced by price in this expensive town. So we were not surprised to find that the motel presented a well-used appearance: bits of our room verged on the dilapidated. However, everything was clean and working: the lady at reception was chatty and helpful; and the sink & storage unit (which we scarcely used) had obviously been recently installed in our room. (We got this room as an up-grade, because our intended room had been taken for an extra night by the previous occupant.)
The location has many advantages, although it is a fair walk to the "business end" of Duval St. and Mallory Square.
All in all, we were happy.

Do not stay here...we paid inflated holiday prices only be be attacked by bed bugs and experience the most horrible night of our lives! Our room looked clean and simple and the motel nicely located, little did we know what lurked behind- it literally ruined our trip! Worse yet, the front desk manager (who looked and acted like a drug dealer) didn't want to deal with the situation. Luckily (after some rigamarole) the hotel owner refunded our stay when he saw the evidence...overall this was one of the most disgusting and traumatizing experiences of my life. DO NOT STAY HERE!!

This is your basic clean, cheap (by Key West standards) motel. No friills but did have a small refrigerator which worked well. While it is located just one block off Duval (the "happening" street) it is over a mile from the Mallory Square end of Duval where the sunset "event" and most of the action is. Trolleys (at $19pp per day) connect nicely until 5pm. Then you walk, taxi, etc. Staff is nice and parking is available and free. Had some ants in the bathroom but they were very small. Our shower was small dark and grim and water flow was slow. Bed (sans headboard) sagged some in the middle but when you've walked the mile or so from Mallory Square, you are able to sleep OK. Only 2 blocks from US southermost point, an easy walk.

This was the only motel that was not booked up for New Years(other than the high end hotels)Anyway,the price was about 189.00 per night w/3 night minimum for 1 queen, when I arrived and got keys to room I was shocked to see that for the price all I got was a bed(no hedboard just mattress and boxspring on frame)night stand w/lamp and an oversized dresser with a 13in t.v..
The air conditioner kept me awake with the loud noise it made and the bathroom is is so small that when you take a shower you can barely maneuver around and the toilet is so close to the walls that you cant take a crap and wipe, and they have the nerve to have 2 pictures screwed to the wall like somebody will steal them(please), no ice machine(the front desk person tells you that they are a budget motel and that there is a store across the street to purchase ice)Oh, BEWARE OF THE CAMERAS. I think the hostile up the street is probably nicer than this place,have already booked for New Years at a place where 189.00 would be worth it. Really South Winds, maybe you should change the name to Gone with the Wind.