The Southwind Motel is an older property but well maintained and extremely clean. Located on Simonton one block off Duval, on the ocean end of Duval in Old Town. Room had two double beds, a mini fridge and recently remodeled bathroom.

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... More

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... More

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... More

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... More

My girlfriend and I found Southwinds the last time we came down in late January and decided to try for Memorial Day. Even for the holiday weekend, it was reasonably priced compared to the other hotels and motels on the island and the location to Duval Street is hard to beat. It is a bit of a walk to the... More

We were worried about finding a cheap motel in key west particularly as its a memorial day but came across this little gem at 89 dollars per night. Sure, it's old and basic, but it's at the heart of key west near too duval street and Bob the receptionist was lovely and helpfully. Pool was great and was very warm.... More

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:... More

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... More