Love the 50s vibe of this motel but still appreciate the modern conveniences. There are two pools but the pool nearest our room was very convenient.i think we had the best room, along with our neighbour. It faced the street but was shaded by a nice garden. We could sit on our little porch, chat with our neighbours, have a drink and watch the world go by. Having a bar, bottle shop and ice cream/donut van on site also added to the convenience. The complementary breakfast and laundry facilities was an added bonus. The food van opposite, the Typsy Rooster sold delicious hot food so no need to go very far for a meal.

The room was small but that is in keeping with the period of the motel. The bar sold me a beautiful a delicious pina colada on our first day. The next day, with a different staff member, the drink I got tasted like a 100% pineapple juice with no alcohol and definitely no coconut cream.. I should have complained but how do you prove you didn’t get the drink you ordered and paid for, if the person serving you says you did.

Staff is always pleasant and helpful.Everytime I have stayed here it has been nice.

The location was amazing, the staff were all very friendly and very helpful! The location has 2 pools, is very close to the beach (3min walk) that includes free towels and chairs, it's directly across from an amazing Cuban Café and small store featuring delicious food and coffee starting at 7am, an ice cream truck on the premises, and adjacent to the Tipsy Rooster whose bartenders were awesome, drinks were delightful, and very good live music daily. It's just far enough away to not be in the "thick-of-it" but close enough to walk everywhere (rent a golf cart/scooter/bicycle or Uber/taxi)

The only thing was the weak shower pressure, but that won't keep us away!

I have been staying at Southwinds for over 10 years when I come to Key West. It's a great location! I either rent a golf cart or trailer my LSV down with me. The whole entire staff is very friendly (guest services, housekeeping, and maintenance). It's located next door to the Tipsy Rooster, a bar with a liquor store. There is a small convenience store across the street for any forgotten needs or junk food cravings (toiletries, snacks, and drinks both alcoholic and non alcoholic, etc). The Southwinds property has 2 fresh water swimming pools, a light continental breakfast (boiled eggs, yogurt, danish, cold cereal, muffins, juice, milk, coffee, and tea). I highly recommend this facility and is exactly why I keep coming back to stay here several times a year!

The prices are higher during season.

Located at southern end of the island so quieter than the upper end of Duvall Street, but this suited us. Nice to relax away from he hustle of Duvall for part of the day. However, several bars and restaurants very close together with South Beach (vouchers given by the Motel for beach chairs and parasols). Short walk from nearest stop for the free to ride trolley. Good size pool. Free continental breakfast provided. Nice to be visited by the local rooster family on a daily basis.

Lack of storage space in Room for cases, but that was a small gripe. Otherwise couldn't fault it.

Location was perfect. Breakfast was good enough. The beverage selection in the lobby was great. We loved the live music every day at the rooster. Bed and pillows were really comfortable. The chairs on the porch were in good shape and we were glad to have them. Large coffee pot in room was a plus.

A few improvements to the room would make a big difference. A full length mirror in the main room and a few hooks for towels and wet bathing suits would be very handy. We rented bikes. I didn't like that the front desk didn't have keys. We had to wait for them to be delivered and almost missed our excursion.

Location was excellent for the event I was attending (very close to the Southernmost point.) Room was clean with lots of outlets and a desk. Enjoyed the free juice all day in the lobby. Enjoyed the outside seating out front (but more shade would have been nice given the heat in July.) Bed was comfortable and the shower was hot with good pressure. AC was stellar and not too loud.

I was expecting some workable windows with daylight but every window was blocked. As all the rooms are ground floor, this is probably safer anyway (but no daylight is not ideal.) Beware that Room #19 shares a wall with the attached bar which has live music (luckily the singer was good) so it's loud until midnight. You are right in the thick of it all so just know this going in. There are two pools, but not enough sun umbrellas to sit under.

Location was perfect, price was fair, small breakfast enough to get you through to lunch, close to major attractions where you could walk, clean rooms, mini fridge was nice in room with microwave and coffee pot.

Bathroom was small but shower 🚿 was decent size. Room small but didn't matter as you were out of the room doing things most of the time.

The staff was very friendly, competent and helpful. The room was generally clean, but the floor got my socks quite dirty as the room is accessed from outdoors. The room had adequate coffee, frig and microwave. The bed was comfy. Laundry was convenient. We were able to use the very nice beach of the Southernmost Resort.

As a non-smoker, it was tough being outside of the room where smokers were often present. Privacy was negatively affected as you went out of your room as outdoor tables were shared. Our room was quite small and drawer space was minimal. Clothes hanhing was minimal and in the room, no closet.

The location and cleanliness were absolutely perfect. The breakfast was minimal, mostly packaged products like muffins, oatmeal cups, & yogurt (but not bad for a free breakfast in the area if you have no dietary restrictions). Super clean & cozy rooms. Space is used effectively, but if you prefer a spacious room, ask about larger suites (or consider somewhere else). Nearby resorts have fairly cheap day passes, so it may be worth booking here and grabbing a pass. I had a wonderful stay and I will be back.

I enjoyed it all. This was a perfect hotel for what I needed.