We spent 3 nights at the Southwind. It started off very sour as there was a sign on the door with a "be right back". After a while of waiting we called the after-hours line posted on the front wall. The lady was NOT happy that we did that b/c it costs them. Well we asked the all-important question-why don't you have a phone number on the "be right back" sign. She said the owner doesn't allow it? After we got that squared away she lightened up a bit. We basically used the place to keep our stuff for our stay there...the beds were hard but that was expected. Maid service was very good, it's just small, but we were happy to get $99/night. Rent bicycles as it's about a mile I believe to all the action on Duval. Just don't expect much from this motel. Oh, we were told on the phone that they had an ice maker, they do not have an ice maker we had to go buy our own ice.

I stayed here twice this summer. The rooms are simple, definitely no frills. Definitely not a place for those who like to be in their room the whole time. However, for those who like to go out and do things all day and just come back to a clean air conditioned room, this is perfect. Beds are a little rough as stated in other reviews but as long as you're staying less than a week, it's not so bad.Great location, one block from Duval street. Very affordable for the area.
Just to note, I would never look at this place and think to stay there, but dont be fooled by the exterior!

When my husband and I decide on a spur of the moment weekend trip to Key West we have found that the Southwind Motel fits the bill. It is economical, and within walking distance to all of the Old Town attractions. Each time we have stayed there the rooms have always been clean and tidy, and the staff is always friendly. We stayed this past weekend and were pleasantly surprised to find that the rooms have started to be renovated and updated. Our room (#11) was quite comfortable and clean. Basic amenities provided, plus a refrigerator in room is especially handy. If you are looking for a plush resort stay, this isn't your place. But if you are in town to play for a few days and want to stay in a quiet, comfortable bare bones motel in heart of all of the activity that Key West has to provide, I suggest you give the Southwind a chance. The room was especially handy for the Hemingway 5K that we ran during our stay. The race started at the Southernmost Hotel across the street, and whose rooms ranged from $272-500+ per night that weekend. I'll take a $99 room any time!

Great location, very close to the southern most point, and about a 20 minute walk to the bars on Duval.
Small rooms, VERY uncomfortable beds and pillows. Didn't get very good sleep.
The rooms were an awkward layout, it seems like it was a larger room at some point and they put a wall up to make it into 2 rooms.
The pool was probably the best part about the stay.
This hotel is ideal if you're just looking for a place to put your stuff and spend very little time in the room.
The staff was rather unfriendly, and be sure to bring your own shampoo and body wash, the hotel didnt even provide bars of soap.