Name: Southwinds Motel
Address: 1321 Simonton Street, Key West, 33040, US

6/10

Pleasant

03 Aug 2026

Anne

Amenities stated a restaurant but there was a bar and donut shop only. It also stated private beach access which we never did find. Overall was good though, very clean. Pool was nice.

8/10

Excellent

02 Aug 2026

Dan

Good place!

4/10

Poor

02 Aug 2026

Ken

The front door of the room had no weatherstripping and daylight abound. It also would not fully shut which left us with a doubt on security. The bathroom door would not shut and continually popped open. The shower had a 1” white caukl ring around it which looked like it was done by a two year old. The cheapness and the lack of maintenance of the room was abysmal. The air conditioner state on 66 but the room stayed warm. It has a kitchenette which was ok. There was no towels at the pool several days ago it is obvious that the owners are very greedy and cheap. I do not recommend staying here unless you just want to sweat and deal with the doors not closing properly

10/10

Exceptional

02 Aug 2026

Mayna

The room had everything we needed... basically a small fridge and a microwave which always helps save some money when on vacation. lol. The place was clean all around and the front desk people were super helpful. They had someone in the office 24/7 so that came in handy when I lost my keys to my suitcase! I had it opened within 10 minutes with their help!
Another FABULOUS part was FREE laundry usage.. it was great having all clean clothes in our suitcases for the trip home and not have to do it all when we arrived!
The location was perfect.. very close to the action but not in the middle of it. We never heard all the craziness on Duval st at night.
The price was great... went in July... would definitely go back.

8/10

Excellent

01 Aug 2026

COURTNEY

Great location. Friendly and helpful staff. Good breakfast. Small, dated room.

8/10

Excellent

31 Jul 2026

John

Good location and price.

10/10

Exceptional

29 Jul 2026

Brian

Small room but just right for 2 people. Charming old-style motel.

6/10

Pleasant

28 Jul 2026

shawn

Location was ok but I have stayed at tons of different locations this was the lowest place I stayed would not stay here again

10/10

Exceptional

27 Jul 2026

Joe

The staff was very helpful and polite, their staff was professional and helpful. Karen the front desk person was awesome. Very helpful and friendly

10/10

Exceptional

27 Jul 2026

Donald

Great helpful staff. Locations was good, not busy but walkable to busy areas .

8/10

Excellent

27 Jul 2026

Yolanda

It was nice

10/10

Exceptional

26 Jul 2026

Holly

Our second time staying here. Great location. Fit our needs. Convenient store across the street. Local bar next door. Lots of food options around motel. We’d stay again.

2/10

Poor

24 Jul 2026

Jacquelin

0000000

Friends

10/10

Exceptional

24 Jul 2026

Ronnie

Great stay Only complaints small tv and low water pressure in the shower. Everything else was excellent.

8/10

Excellent

21 Jul 2026

Blake

It was soooo unbearably hot it would have been nice to go in the pools but they were both like bath water and the small pool was very dirty. Might I suggest you put cool water from the hose into the pools several times a day !!

Friends_and_family Family

10/10

Exceptional

21 Jul 2026

Saige

Everything was fantastic!!

Family

8/10

Excellent

21 Jul 2026

Chris

Very good location! Cute older place it was clean and nice. Great grab and go breakfast.

Family

10/10

Exceptional

20 Jul 2026

Dallas C

It was what you would expect as an old schooler motor lodge. Great location to get to South Beach as well as down Duval street to all the stores, restaurants and bars. Great bar with some goo live musics right there on location with a liquor store to boot.

Friends

10/10

Exceptional

20 Jul 2026

Aly

Room was clean, pool was cool. Breakfast was appreciated!

Partner

8/10

Excellent

19 Jul 2026

Mary

The bathroom had no air or heat or exhaust fan.

Friends

6/10

Pleasant

18 Jul 2026

Raymond

Not the greatest. Too many addons. You have to pay for parking. Too many taxes.

Friends

8/10

Excellent

18 Jul 2026

Raul

Staff was very courteous and helpful. Our room was very clean and comfortable. A good, fresh variety of items, along with coffee. milk, and juices were available for breakfast.

Family

10/10

Exceptional

14 Jul 2026

Alexa

Great overall!

Friends

2/10

Poor

13 Jul 2026

Daniel

I got slapped with extra amenities fees when I arrived. Then on day 2 my ac went out at night. They semi fixed it for the day but then it went out again the next night. My room was 85 degrees during the night. The next morning they could not connect me with a manager and the staff in the lobby was terrible. They were rude and not helpful. I never raised my voice and was never mean. I just stated what the issue was. The rude girl just said the same line repeatedly to me. No apology or anything. At least the maintenance guy later was nice but that was a couple hours from checkout. I will NEVER stay here again. I’m still fighting to find a manager so I can get some credit or refund for my stay.

Friends_and_family Family

10/10

Exceptional

13 Jul 2026

Michele

great location!

Friends

8/10

Excellent

13 Jul 2026

Eunices

Good place, clean and quiet.

Family

10/10

Exceptional

11 Jul 2026

Lesley

We spent a long weekend at this hotel for my birthday. The room was nice and cold and the location was great. We especially liked the bar next-door and the Cuban restaurant across the street.

Friends_and_family Friends

2/10

Poor

10 Jul 2026

Paul-Emile

Just wanted to write after our 2 nights stay at your Motel last week-end. We stayed in early july.

We booked a standard room 1 queen bed. Nevertheless, after arriving, we quickly became disappointed by first seeing that the room was looking much different and smaller from what we booked online. Then the condition and cleaniness of the room was absolutely not something we expect after paying almost 800$ for 2 nights. Here is a brief overview of what we had :

— Window A/C unit : really noisy, almost impossible to sleep with it, the person at the lobby told me that the maintenance guy could come, but for 2 nights i would have liked it to be ready from arrival

— Outdoor side of window A/C unit: rusted, corroded casing and bent, dirty condenser fins.

— Ceiling exhaust vent: heavily clogged with thick dust and lint, badly needing cleaning.

— Vanity countertop: laminate edge is peeling

— Baseboard / wall corner: cracked and separating trim with visible mold or grime at the floor joint.

— Shower grab bar / wall flange: rust staining around the fixture and badly installed with visible screw almost falling

All of that made us feel really disappointed from the experience we had at your motel , and i would not recommand someone to go there if they want something worth it.

Partner

6/10

Pleasant

09 Jul 2026

JOSEPH

Good

Friends

6/10

Pleasant

07 Jul 2026

Sabrina

Great location. I rented a car & didn't drive it my entire visit. I was able to walk everywhere.
Liquor store & bar built in, so that's convenient. Lol
It's definitely an older Motel, so things are older. I was surprised when she handed me an actual key for my room. You don't see that any more 😁

Self

10/10

Exceptional

06 Jul 2026

Cary

Excellent Staff bicycle rental on-site

Partner

10/10

Exceptional

06 Jul 2026

Magdalena

Great location good place to stay!

Friends_and_family Family

10/10

Exceptional

05 Jul 2026

Ronald Stephen

A

Self

10/10

Exceptional

05 Jul 2026

Daniel

Excellent staff and a fun place to stay.

Self

8/10

Excellent

05 Jul 2026

Gustavo

Place was close to everything

Friends_and_family Friends

10/10

Exceptional

04 Jul 2026

Anthony R

It was a great trip! Close to many things.

8/10

Excellent

03 Jul 2026

Frederick

The room was clean, the staff was nice and very efficient. Breakfast was good, outdoor pool was nice. The only thing that could be improved is the air conditioner and having a ceiling fan.

Partner

10/10

Exceptional

03 Jul 2026

Gregory

I

Family

6/10

Pleasant

29 Jun 2026

Kristin

There were ants in the room. Just a few to start but then we had a late night pizza and next morning pizza was invaded and all over the place. The staff was friendly and helpful. Pool was nice but there were leaves from trees in section that could have been taken care of better. A/C was working great.

Partner

10/10

Exceptional

28 Jun 2026

Lisa Michell

Great, fun place to stay in Key West! Staff was amazing, the bar with live music was a plus!!! Very clean and cozy property.

Partner

6/10

Pleasant

28 Jun 2026

Alexandra

The breakfast was nice, items like bagels, yogurt cereal, muffins, bananas and oranges. Juices and coffee.

The pool was really warm, not sure if it had a heater or if it was from the sun because it has been very hot. But the pool was clean and there were always fresh towels.

The AC units are not maintained and are severely corroded. The rooms are very small but clean. Housekeeping was very friendly and gave us some extra towels when needed.

Overall served its purpose of a fast weekend. The bar was nice and the food truck outside had great mini donuts and ice cream.

There is a $20 parking fee per night, AND a $30 “amenities” fee per night as well. The washing machine was dirty and did not work. We tried to do a small load and the washer never drained. It was just stuck with dirty water. I think the fee’s are a little extensive seeing as it’s almost $300 a night for a king bed single room. Overall was ok.

Shaunda( I am probably spelling her name wrong) was AMAZING. Super helpful and very nice. She assisted with our golf cart rental which I would def recommend.
We will be back to Key West but will probably try a stay at another place.

Partner

10/10

Exceptional

28 Jun 2026

Anthony

Fantastic location with excellent staff!

Friends_and_family Family

10/10

Exceptional

27 Jun 2026

roger

Extra friendly staff

Family

10/10

Exceptional

27 Jun 2026

Michelle

Staff very helpful and nice.

8/10

Excellent

26 Jun 2026

janice

Great place to stay because you are close to everything. Walls are thin so it can get loud. Good breakfast, great pool and super helpful staff.

Self

10/10

Exceptional

24 Jun 2026

Roxanne

It was a great place to stay! The staff was awesome!

Partner

10/10

Exceptional

24 Jun 2026

Franchesca

Pool was clean and room was clean

6/10

Pleasant

23 Jun 2026

David

It's a perfect case of you get what you pay for.
Water pressure in the shower was nonexistent. The free continental breakfast was on a first come first serve basis. That was never stated in anything online describing the facility. It was a good enough facility for what it cost.

Partner

10/10

Exceptional

23 Jun 2026

Glenda

Hotel was quaint and nice. Very clean, pool was clean. Very nice staff and good breakfast.

Family

6/10

Pleasant

23 Jun 2026

Sutton

Close to duval and southernmost point

Family

10/10

Exceptional

22 Jun 2026

mariuska

Todo limpio.

Partner

10/10

Exceptional

19 Jun 2026

Robyn

Fantastic stay. Loved everything on the property. Staff was extremely helpful

Family

10/10

Exceptional

19 Jun 2026

Sourav

Location and staff were great.
Toilets were clean but, it would be better if there are exhaust fan in toilet.

Family_with_children

10/10

Exceptional

18 Jun 2026

Melissa

Lovely place close to everything! Amazing staff.

Partner

10/10

Exceptional

16 Jun 2026

Jacqueline

I am the General Manager of a hotel. I am not an easy person to impress in terms of hotels. The staff at this hotel stands apart. I had a wonderful stay, in particular due to the lovely young woman who checked myself and my daughter in. Thank you for everything!

Family_with_children

10/10

Exceptional

15 Jun 2026

Kim

The room was clean and nice. I liked having a refrigerator, coffee maker and microwave. It was a little warm in the room but it was extremely hot outside. We didn’t take advantage of the breakfast.

Family

8/10

Excellent

13 Jun 2026

Erik

The room was very comfy, and the bedding/pillows were great. The only downside to me is that the center parking lot floods, and you might have to talk through inches deep water to get across it. And the pools feel like you are in a concrete jungle in an urban surrounding, as opposed to a tropical feeling.

6/10

Pleasant

11 Jun 2026

Paul

Plan on spending more for amenities! We were hit with an additional charge at checkin! Nowhere in our reservation were we told about the additional charge

Partner

8/10

Excellent

11 Jun 2026

Kimberly

Property was close to everything

Family

10/10

Exceptional

08 Jun 2026

Caridad

Clean and cozy pool area.

Partner

8/10

Excellent

08 Jun 2026

David

It is a bit antiquated but clean. The pool was very nice and warm. The selection in the liquor store was pretty good. The bar and live entertainment were good as well.
Really liked the vibe of the whole place.

Partner

10/10

Exceptional

07 Jun 2026

Wendi

A beautiful Key West Motel! Will definitely stay there again!

Partner

10/10

Exceptional

05 Jun 2026

Dmytro

Older but remodeled inside hotel. Very clean and fresh. A bit noisy AC.
Decent breakfast. Sweet spot. Extremely close to everything. Will book again

Family_with_children

10/10

Exceptional

05 Jun 2026

Erin

It was a good stay. Close to the ocean and restaurants.

Friends

8/10

Excellent

04 Jun 2026

Robert

Basic bare bones room, not new, its a motel but what else do you need in Key West, place to sleep and shower, this is a place to crash and isnt fancy but location is great, market across the street, bar and liquor store in front of motel, 5 min walk to Duvall and 1 block from beach. It does the job and has a pool too and parking!!!

Friends

8/10

Excellent

02 Jun 2026

Trudy

The rooms are nice. We like the continental breakfast before we head to the close by beach. You can get passes for a beach chair and towels. We like the convenience of the location. The only thing we didn't like is that the pool closest to our room was locked before the actual time, but we were able to go to the other pool. There was also an very early morning truck that emptied a dumpster. The staff was nice and we were able to leave our luggage after check out, because we had a late ferry trip.

Family

10/10

Exceptional

31 May 2026

Memphis

The rooms are nice. They provide necessary amenities and are cleaned well. Not a lot of space, but fair for a motel setting. There is loud music next door at a bar, which I enjoyed, but that’s something to be aware of if you’re a light sleeper. The staff was helpful and this area of the island was very nice. Overall, it was a nice stay!

Partner

6/10

Pleasant

31 May 2026

Michael

This place is fine to rest your head if you want to be in Old Town on a budget. But even budget prices are way too high for what is essentially a very dated motel. Our room wasn’t ready until 4, but we were allowed to leave our bags unsecured under a table in the lobby until then. The air conditioner thudded loudly all night against the wall because it was improperly installed, and the bathroom was massive with a ton of dead space around the narrow prison shower and tiny vanity. Everything shabby. The small fridge, TV, and coffee maker were all stacked on top of each other and shared the same outlet. When the power went out in the middle of the afternoon, the staff did not seem particularly concerned. Breakfast was included, but nothing special—muffins squashed in plastic wrap, weak coffee with grounds floating in it served in flimsy styrofoam cups. Yogurt. Bagels. They charged extra for amenities—use of the small pool in the parking lot and towels for the beach—that did not seem to be worth the extra $65. Housekeeping only comes every third day. Beggars can’t be choosers. But if you’re not desperate or on a tight budget, look elsewhere.

Friends_and_family Friends

6/10

Pleasant

28 May 2026

Dawn

Didn't realize you had to pay to park a vehicle..very disappointed..

Family

10/10

Exceptional

28 May 2026

Kathleen

It's an old motel so it is aged. But, it is well maintained, the staff was wonderful,, the location was ideal, and the price was very reasonable for Key West.

Friends

10/10

Exceptional

28 May 2026

Dakota

Pool was nice. Breakfast was minimalist but good. Location is great

Friends

8/10

Excellent

27 May 2026

Jerry

Nice hotel way cheaper than others nearby in Key West. We were near the bar behind the hotel and it was quite loud until about 11 pm, but other than that I am satisfied and would stay here again.

8/10

Excellent

26 May 2026

Richard

Small, clean & tidy room. Good location for walking around. Little bar next door had great live music.

Family

8/10

Excellent

24 May 2026

Kamryn

Good location

Family

8/10

Excellent

23 May 2026

Annie

Good location and quiet place to unwind at the end of a busy day. Pricey but of course it's Key West. Very basic breakfast.

Friends_and_family Friends

6/10

Pleasant

21 May 2026

Deborah

Did not use to pay for parking Now $20 a day Breakfast was ok but nothing special

Partner

8/10

Excellent

20 May 2026

Jennifer

The rooms were very clean and had everything we needed. Coffee pot/microwave/refrigerator was a plus - every hotel we look for has to have those three things. The staff was friendly and was able to check us in early. The only issue was the noise factor - our rooms were close to the front of the property so the music from the bar and traffic from the street was a bit frustrating because we are used to quiet, but other than that the stay was great.

Friends

8/10

Excellent

18 May 2026

Linda

Clean room. Everything is in walking distance. The room itself was super small and tight once you start living there.

Friends

10/10

Exceptional

18 May 2026

Roxie

We had a problem with the reservation but the staff was very efficient with fixing it and put our minds at ease. Our stay here was everything thing we needed. I love the nostalgia of the place.

Partner

10/10

Exceptional

18 May 2026

Deborah

Room was spacious and right outside to the pool.. bar and live music on the property. Convenience store across the street.

6/10

Pleasant

18 May 2026

Michael

It's Key West...you don't go there for the hotels!

Friends

8/10

Excellent

17 May 2026

Cindy Everhart

Great location! Property was great, water pressure in shower was very poor!

Friends

10/10

Exceptional

17 May 2026

Theresa

Conveniently located, basic hotel was decent for the price. Staff help us rent scooters.

Partner

6/10

Pleasant

16 May 2026

Kendall

The breakfast was not great. We had no maid service the whole week. It is a good location. The bar in property is fun.

Partner

4/10

Poor

16 May 2026

Sheila

The photos for this resort are deceptive. The resort is run down with sagging blinds, big gaps around the door (letting hot air and noises in), bathroom window that opens with no lock or screen on it (very unsafe, anyone could crawl through it into the room), coffee carafe was different brand than pot so didn’t fit tight, room smelled like urine, many smokers at resort right outside the door, shower water too hot when adjusted for comfort water was barely a trickle, the in room air conditioner did not keep the room cool it was warm our entire visit (fixing the gap around the door would help this). The power went out while we were there, we called the resort number with the only option to leave a message no emergency number. Luckily the power came back on within an hour and a half. The continental breakfast had good options. Location is close to southernmost buoy.

Family

10/10

Exceptional

14 May 2026

Eber

Excelente servicio y muy buen lugar de la propiedad

Partner

6/10

Pleasant

12 May 2026

Diana

Parking fees extra. Resort fees added because used 3rd part booking. Breakfast was fresh. POOL was clean yet not award winning.

Partner

2/10

Poor

12 May 2026

Ronald Peter

Dirty bathroom. Palmetto bugs in the shower. Loud air conditioner

Friends

8/10

Excellent

12 May 2026

Rebecca

This hotel is very well located, close to the beach and southernmost point. It is an older property so not a lot of amenities, the staff was friendly and there was a small complimentary breakfast.

Friends_and_family Friends

8/10

Excellent

11 May 2026

Shari

This hotel is very old but well maintained. The location was 1 block from Duval with many restaurants choices. Very close to the Henningway home and tour. They offer a private beach access providing a chair and towel. The breakfast was ok however the muffins were delicious. There is a very nice outside bar on the property so made it very convenient for a night cap. There is also a ice cream shop with fresh donuts on the property. There is a Cuban Deli across the street with delicious breakfast offerings and lunch.

Partner

8/10

Excellent

10 May 2026

Michele

Loved the liquor store/bar on property that had live music during our stay. Across the street from a small market and walking distance to beach with chairs and umbrellas. The room was incredibly small but in fairness it worked for us. We showered and slept in the room so didn’t need much. The air conditioner had a hard time keeping the room cool but we found it acceptable. The pool was nice and the staff very friendly.

Friends

6/10

Pleasant

08 May 2026

Saleta

The rooms were simple but cute in that vintage sort of way. Breakfast isn’t really helpful unless you just want breads and yogurt. Room seemed cleaned but definitely saw black hairs on the towels that didn’t belong to us. No ceiling fan in the bedroom so it does get stuffy. Very cold mini fridge in the room. Mattresses are not comfortable and the edges of them sink a lot. Parking is close to the rooms which is nice. Very convenient walking to local restaurants and historical spots. Overall not a bad stay but not sure we’d choose it again if there were other options.

Friends_and_family Family

10/10

Exceptional

08 May 2026

Gwendolyn

Breakfast food no hot food but would get you by until lunch. Clean room but could use a shelf or vanity to set personal articles on. Room is small but has everything except could use a small chair with a back on it. Nice pool. Staff was great!

Partner

10/10

Exceptional

08 May 2026

James

Basic ROOM but FANASTIC location

10/10

Exceptional

07 May 2026

Debi

Adorable motel with a continental breakfast, two pools and a short walk to the beach. I would stay here again.

Family

10/10

Exceptional

06 May 2026

Richard

Very nice place to stay. The breakfast was good, pools were nicely kept very clean and always towels available. The best part was the use of the beach, great chairs and towels provided. The area was very quiet and comfortable

Friends_and_family Friends

10/10

Exceptional

06 May 2026

Janis L Parks

Cozy vintage motel. Friendly helpful staff. Continental breakfast daily…plus coffee maker (and supplies), microwave and fridge in room. Walk to many attractions. On-site outdoor bar for your nightcap! We loved it!

Partner

8/10

Excellent

05 May 2026

Sue

The room was nice, my only complaint would be that the air conditioning is particularly loud! Earplugs are essential unless you sleep like the dead.

Friends_and_family Friends

10/10

Exceptional

04 May 2026

Billi

We loved our stay! Location was perfect. Could walk to bars and restaurants. Great onsite bar with live music. Room was set up perfectly with space for our family. Staff was wonderful as well. Will definitely stat again!

Family

10/10

Exceptional

04 May 2026

John

Satisfied with everything

Friends