Southwinds Motel

Great older hotel at the ocean end of Simonton Ave. Great coffee shop on the corner and plenty of food options right in a 1 block radius. Oh yea, Tipsy Rooster right out front with live music most days, bar, and liquor store. 2 nice pools on site. Property is very well maintained. Wi-Fi was problem-free for my wife's online business requirements. Convenient parking onsite. Bike racks, bike rentals, and even onsite scooter rentals.

My only issue was that our room did not have any dressers so we lived out of our suitcases for 5 nites.

Breakfast was good, great location, bike rentals were awesome to get around the island for sight seeing.

At the eastern end of Key West, Southwinds is "close enough" and yet "just far enough away" from the crowds on Duval Street. Everything is easily accessible, so it's nice to get away from the noise. Mornings are so pleasant, listening to the roosters crowing! Room 7 is generous in proportion and it was wonderful to have a kitchen area for our snacks and beverages.

The floor looked clean, but was so dirty that the bottoms of our bare feet were black within minutes. There were no convenience shelves in the shower stall for soap or shampoo, etc. There were no grab rails in the shower stall. There were no bathroom shelves or counter space for personal items.

What great little motel! Our suite was larger than I expected and very comfortable. Bike rentals on the property made it easy to get around Key West. Location was far enough off the busy part of Duval to be quiet, but close enough to quickly get to all the action. The breakfast offerings were awesome and plentiful. Most important, ever staff member we interacted with were so nice and pleasant to talk to. This was our first stay at the Southwinds but it definitely will not be our last!

I was so disappointed we only booked three nights at the Southwinds. For some reason, time seems to go by much quicker when on vacation in Key West. We should have booked a week at this delightful resort!

The Southwinds motel seems to be an older but excellent shape motel. My room (a single) was small but adequate. The location was excellent, especially if you bring your bicycle. Excellent restaurants nearby, Duffy's Steak House (a little pricey but food was excellent) and Seven Fish (a 5 Star seafood restaurant) Both restaurants are on Truman Ave.

Price. The Price is quoted "plus taxes and fees" One of the "fees" is a $60.00 per day "resort fee" Total price came to about $240.00 per day for a small hotel room with a refrigerator and microwave.

Our room at first was plenty. But then we had issues with our shower. The office was very helpful. The location of the motel made it easy to get around to all the sites.

Our room the hot water would not work properly. So they had to jump us around one night and then moved us to another hotel for our last two nights.

The room had everything I needed. The cleaning staff were respectful and did a great job. The location was outstanding. Breakfast was fine, considering the COVID restrictions.

My room wasn't ready at 4 PM and I had to wait a bit. The window looked onto a wall - disappointing. An adjacent customer snored so loudly it interfered with my sleep. Low water pressure in the shower.

Great location, complementary washing facilities on site, allowed an hour later check out complementary. Although our room was very clean, it was in great need of updating. Even fresh white paint on the bead board  and wood would be a huge improvement.  It looked old and dated and that would certainly freshen it up.  One of the things that aggravated me was my flight was canceled because of the hurricane that came through Key West and on the western side of the Florida peninsula. The motel would not allow me to cancel one day and come in later. I ended up paying for two nights and didn’t even get to stay there. I feel like that was poor business, and I will probably never stay there again as a result. The front desk staff was not very friendly, but they were helpful.

Even though the rooms were very clean, they were so dated that it looked like they had not been kept up well. Time for a mini facelift.

What we liked about the Southwind Motel is that is in oldtown and is close to most museums ,atractions ,restaurants and shopping ,also the beach .It was very peacefull during the day and night ,and the tipsy rooster bar had very happy and good vibes with a music performers every night ,my wife and I loved the place we also use one of the pool which was very clean and warm. Also rooms are very clean and they do the house keeping everyday .Hotel Staff was very nice and welcoming .All around the property was very clean and we also loved the rooster treats ice cream truck in the corner.

Many of the reviews talk about the space being outdated or "rundown"... that wasn't our experience. Yes, it is serving shabby chic, but our bed was comfortable, the bathroom big, the A/C (yes a tad loud) working perfectly in what was a heat wave where all of Key West felt like 115 degrees, and everything fit into what we were seeking for the excellent price provided. Many key places within walking distance, a bar next door, buses to get you to the square, and more! Would 100% stay again.

There were a few ants, but we didn't mind them as we were just there for a couple of days. Could have been more shade at the pool.