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.

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.

Loved the location, the vibe, the room, the amenities. Would definitely stay again in the slightly off-season when the rates are a bit lower. Easy walk to water, tourist sites, good restaurants, etc. The room was not fancy but it was very beachy and comfortable. The swimming pool was nice and warm. A bar and an ice cream shop on the premises, and across the street from a quaint grocery store/deli/Cuban coffee place. Bikes/scooters available. A couple of blocks from hop on-hop off bus stop. And of course, the ubiquitous KW chickens running around.

Liked it all. It was just BLAZING hot during our visit, but the hotel couldn't do anything about that. :)

It's in a fantastic location. You can walk 5 mins to the beach at the end of the street, or the Dog Beach next door, walk to tons of restaurants, shopping, bars etc. Parked my truck for 2 days! Hotel staff was amazing! Room was small but cute, clean and comfortable for 2 ppl. Bar next door, live music until 11, great vibe, met some amazing ppl. Room was quiet, slept great. Highly recommend.

Breakfast limited to muffins, danishes, coffee, OJ or AJ. Hard boiled eggs in a plastic package, oatmeal. It was OK for our short stay but longer than 2 days, you'd need to find a breakfast spot.

I loved nearly everything ❤️ two pools to choose from, 1 is heated. There each surrounding the rooms. The room was HUGE with a bar! Our fridge was big enough and it fit our bag of ice! Their services came every day around 11. Semi attached was a bar with live music 🎶 🎵 ❤️ we were located around the corner from everything. I wish I didn't have to leave!

Unfortunately, they did not have any options for streaming......no Netflix, hulu, etc. You have to really work to find the sweet spot for the water pleasure. I found it. My friend, however, did not.

The staff was fantastic. Friendly, SUPER helpful with getting me a golf cart delivered to the property and when exiting they returned it for me. I love the drink machine in the lobby and the delicious coffee provided in the morning. The cleaning staff was friendly and very prompt each day. Our room was very clean and comfortable. When you enter the property driveway, you are instantly in a private secluded area that makes you really feel like you are on vacation. You are close to a food truck, across the street from a small grocery store for last-minute and other items you may need. I cannot say enough about this place. We will DEFINITELY be back soon. This is the perfect Key West spot.

I have ZERO complaints or dislikes about the property.