Name: Southwinds Motel
Address: 1321 Simonton Street, Uptown - Upper Duval, Key West, Florida, United States of America, Key West, Monroe County, US
Price range: $121–$418 per night
Rating: 8.23

What guests think

At Southwinds Motel, travellers consistently praise the walkable location near Duval Street and Southernmost Point, friendly staff, and laid-back, old-Florida vibe, while noting compact, dated rooms with tiny bathrooms and occasional noise from the on-site bar.

Facilities include two small pools, beach chair and towel access, free parking and laundry, plus scooter and bike rentals, though parking can be tight and some amenities are occasionally out of order. Most guests find rooms clean, but feedback on deep cleaning is mixed, with sporadic reports of ants or roaches and housekeeping only every three days or missed service. The complimentary continental breakfast is simple grab‑and‑go and convenient, but it is not a hot breakfast. Overall, it suits travelers prioritizing value and proximity over space and modern finishes.

Facilities

Cleanliness

Rooms

Service

Location

Dining

Was this helpful?

AI-generated summary based on recent guest reviews

Facilities

Two small pools, beach chair/towel access, free parking and laundry, and on‑site rentals are appreciated. Some drawbacks include tight parking, occasional noise near the bar, and intermittent maintenance issues (e.g., pool or ice machines).

Related guest reviews

8

Linda

Apr 12, 2025

·

Stayed 3 nights

The staff is excellent. Standard continental breakfast. While the property is older it was very clean and comfortable. The bathroom is a bit small. Loved the bar attached to the property with live music.

8

Veronica

Jan 14, 2025

·

Stayed 2 nights

Super good location - close to beach, restaurants, shops. Heated (but very small) pool (+ one which was not heated). OK complementary breakfast (coffee, juice, muffins, cereals, egg etc). Very quite area Good free parking Good WiFi A small bar on the premises with live music Silent aircon Free sunchairs/towels at the beach I would stay here again. :-)

6

Deborah

Aug 1, 2025

·

Stayed 1 night

The staff was fine, not particularly friendly. Parking was not good. The second pool was out of order, so the one pool was crowded.

10

Paul

Nov 9, 2025

·

Stayed 3 nights

Keep in mind it’s a motel! Staff were very friendly and the place was clean, as was the bathroom. Never entertained the two pools they have but people seemed to enjoy them. I think my only don’t is the property owns a bar next door and if your room is next to it - it can be quite noisy. Otherwise if ya not looking for all the fancy frills go for it, I’d stay again. They accommodate parking too, we rented a golf cart and it was no problem parking on the property. Enjoy!

10

Cyrenah

Jun 25, 2025

·

Stayed 4 nights

Was very clean, air conditioner worked very well, pool was good, but closed pretty early. Great value considering its one of the cheaper places in Kwy West. Will definitely be staying there for our next trip.

10

Susan

Jun 28, 2025

·

Stayed 1 night

This property is amazing. Two pools, one heated. Free laundry (with detergent!). Front desk did magic and got me my room for a second night. Coupon for free umbrella and towels at the beach around the corner. Go get a Classic Cuban from Ana’s Cafe right across the street. Right on the Duval Loop Trolley. Great value for money. Highly Recommend!

8

Victoria

Oct 28, 2024

·

Stayed 3 nights

The location is good- near the southernmost point, walkable access to the main area on Duvall. The rooms are spacious and clean, property has 3 pools and parking. There’s a resort fee but you have that wherever you stay in key west! They also have complimentary breakfast items in the lobby. Would stay here again.

8

Tara

Nov 11, 2025

·

Stayed 5 nights

We love our stay at Southwinds. There are a couple things that could make it much better: 1. Some hooks on the shower door or bathroom wall for towels. 2. A bit more water pressure or a new shower head. Other than that - it's always a pleasure staying at Southwinds. We love the location. It's quiet. It's in walking distance to many of the locations we love. The Tipsy Rooster is a great bonus also. The beds are comfortable. The AC works great. The pools are amazing.

8

Stacy

Nov 5, 2024

·

Stayed 1 night

Great rate for Key West. Bar on property. We actually had the room attached to the bar. We sleep with a sound machine & didn't hear a thing. Pool had lots of leaves in the filter. Room was basic, but you don't need much more in Key West. Bed very comfortable.

8

Crystal

Jul 1, 2025

·

Stayed 4 nights

It is everything you need. Clean rooms, hot showers, two pools, ice and washer and dryer. Small breakfast and on the quiet end of the adventures. Grocery store across the street, ice cream and bar/restaurant on site. Excellent pricing and friendly staff. Thank you for an incredible girls trip. We will see you soon.

Was this helpful?

AI-generated summary based on recent guest reviews

Cleanliness

Many reviews note clean rooms and grounds, but consistency is mixed. Recurring issues include infrequent or missed housekeeping (about every three days), bathrooms/floors needing deeper cleaning, and occasional pests such as ants or roaches.

Related guest reviews

6

Janet

Sep 28, 2024

·

Stayed 6 nights

This was my 4th time staying at Southwinds and probably my last. The motel's policy to clean rooms every 3rd day is a bad one. We had garbage overflowing and a pile of wet dirty towels on the bathroom floor. During our week long stay, our room was cleaned once.

4

Alexandre

Aug 5, 2025

·

Stayed 1 night

Bed bug on myself and my pregnant wife. :(

10

Terri

Sep 9, 2025

·

Stayed 2 nights

Everything was clean, staff was friendly and a great location

4

john

Jan 21, 2024

·

Stayed 7 nights

Room was surface clean, but bathroom vanity sides were decaying from water damage. Mildew on bathroom ceiling. Bathroom tile needed a deep clean/steam. (Have pictures of all). Disappointed in room condition as we have stayed at Southwinds multiple times, and recommend them to everyone we know coming to Key West. Not sure we will stay here again.

6

Darrell

Sep 21, 2024

·

Stayed 1 night

The people were very nice, but bugs in the room and pool dirty, breakfast was good. Location is grea5

10

Cheryl

Mar 3, 2024

·

Stayed 2 nights

The property was well kept how ever the floor in our room was filthy . Your feet turned black because the floors were so dirty.

6

Ava

Jul 24, 2025

·

Stayed 4 nights

Our room was nice. AC and wifi worked well. The area around the motel is nice. Simple, but free breakfast every morning. Only issue was our room never got cleaned during our 5 day stay and staff shut us down when we asked about it.

10

Ashley

Jul 28, 2025

·

Stayed 2 nights

While the property is older the rooms were clean and cold which was much appreciated. Staff was excellent and friendly. I was a little worried as the seal around the doors and the AC unit could stand to be addressed but no issues and the room served it's purpose. The TV is very small but who goes to Key West to watch TV? Overall I was pleasantly surprised and would stay at the motel again.

8

Denise

Sep 9, 2025

·

Stayed 1 night

Great location. Place was clean and neat. Leary about motels but this one was very nice. Didn't get to use all the amenities. Would suggest.

4

Aneta

Jul 25, 2025

·

Stayed 4 nights

I rarely leave negative reviews, but this hotel was truly below acceptable standards. The room was in dire need of upgrades — everything felt old, worn down, and poorly maintained. The floor was filthy when we arrived, and to make matters worse, the tub still had hair in it from a previous guest. That alone was enough to make me question the cleanliness of the entire room. The AC unit was not properly insulated, and during a thunderstorm, rainwater actually started leaking in through the unit. It was a huge mess and made us feel completely uncomfortable and unsafe. The pool was also a major letdown. It looked unkempt and murky, clearly not cleaned or properly maintained on a regular basis. We had looked forward to using it, but after seeing the condition, we decided it wasn’t worth the risk. Overall, I would not recommend staying here unless significant improvements are made. Cleanliness and basic maintenance should be a priority — unfortunately, this hotel failed on both fronts.

Was this helpful?

AI-generated summary based on recent guest reviews

Rooms

Rooms are generally small with very tight bathrooms and dated furnishings; some units are more spacious. Comfort is basic with small TVs and variable AC, and light or music can affect rooms near the bar; in‑room Wi‑Fi can be spotty.

Related guest reviews

6

Linda

Nov 12, 2025

·

Stayed 2 nights

Room is very small with nowhere to put things. However it was clean. Excellent location for walking all around key West. Breakfast was small.

6

Barry

Oct 25, 2025

·

Stayed 3 nights

Tiny rooms. Tiny TV. The bathroom is so small you can’t even close the door while sitting on the toilet. The breakfast was just a counter with some packaged muffins, yogurt packs, packaged eggs.

6

Craig

Apr 30, 2024

·

Stayed 1 night

Dated, small but clean. Noisy AC. Not quite what you see on the web. BK not open til 10:00am. Continental at that. Would I stay again. No. Can get bettet accomodations for next to same price.

6

Nicola

Aug 30, 2024

·

Stayed 1 night

This motel desperately needs an update, the rooms look like a typical 70's offering, I was expecting Clint Eastwood to turn up with Clyde! The walls have really out of date wood mouldings that take up the bottom half of the walls, the shower is nothing like the stock photo held on Expedia. It is all tiled, again in the 70's, and looks like a shower from a public swimming pool changing room, so also unsafe as it's slippery. The car parking / tarmaced area outside the rooms was appalling, it rained heavily during the afternoon and the drains could not cope, with the ground being extremely uneven, you had to paddle through the water which came up to your ankles. I booked this property because of it's proximity to Duval Street which according to the PR is all about pubs, clubs, dining and families, again a major let down, not what it's made out to be at all.

6

Christina M

Dec 12, 2024

·

Stayed 2 nights

Unfortunately our room was directly Next to the rooster bar and we heard the people In there and the music well into 3am every night - made for very poor sleeping conditions. Also when showering the hot and cold handles did not work, made for very cold Showers which was really too bad, wouldn’t recommend or stay here again

6

Tequesta

Jun 20, 2025

·

Stayed 3 nights

Location is excellent. Property needs updating especially if they are charging the same rates as fees as surrounding hotels. The check in lady was very rude. Looks like she wanted to go home and busy speaking to others instead of completing my check out. The AC unit in the room barely blew cold air and when we said something they brought us a fan.

4

Stacey

Aug 21, 2025

·

Stayed 3 nights

The reviews for this motel were great so I had no worries when I booked it. But it’s fair to say this place is incredibly tired and run down. the exterior of the motel is in need of some tlc, and I hoped that it was only the exterior that was tired. Whilst the rooms were huge, they were badly in need of renovating, there were cracked and peeling walls, and very dated and tired furniture. Whilst it appeared superficially clean it needed a good deep clean. Although we booked 3 nights we left after 2 as we really didn’t feel comfortable here. It could be beautiful if renovated, but with the half hearted staff we saw, I can’t see any changes happening any time soon.

6

Iva

Oct 25, 2024

·

Stayed 2 nights

Friendly staff, great location. Rooms are a bit tired and dated but clean. Bed is comfortable. Washroom is very small so if you are a larger person it maybe too tight. It worked ok for us.

4

Ronald

Feb 13, 2024

·

Stayed 3 nights

location was good noise from bar music was loud under soffet lights shine in the rooms

10

david

Apr 10, 2025

·

Stayed 1 night

Nice area. Very convenient. Wi-Fi not reliable in room but strong signal outside. Wasn't a problem.

Was this helpful?

AI-generated summary based on recent guest reviews

Service

Staff are frequently described as friendly, helpful, and accommodating (early check‑in, local tips). However, some guests report rude or unhelpful interactions, key/check‑in mishaps, and slow responses to housekeeping requests.

Related guest reviews

6

Louise

Aug 5, 2025

·

Stayed 1 night

the room we were given was not handicap friendly. the pool outside our door was out of order. the step into the room was hard to manage with my walker. The girl at check-in was not very friendly and seemed bothered. Nowhere in the room for a handicap person to sit. Brought a chair in from the pool.

6

Hallie

May 14, 2025

·

Stayed 8 nights

The workers were quite literally the only damper. We were told we would have housekeeping come every 3 days. When the 3rd day came, we put our towels out on the floor to be picked up. When we came back the room was still not cleaned and dirty towels still there. Went to desk the next day to ask about housekeeping and when we told them they never came they said “that’s not good.” Oh? So then we asked for towels so we could at least shower. We were told no housekeeping was on the way. After 30 min we called and were told housekeeping was coming. Housekeeping came and we were kicked out of our room so they could clean, again all the while we were waiting all we wanted was clean towels so we could shower and leave for the day. When I asked for again shower towels days later I was given a beach pass? I asked “how does this get us shower towels?” Then the worker laughed and said she blunt I said “beach pass” ok idk how you get beach pass from shower towels but ok. Maybe look into retraining people who don’t know left from right.

10

Jennifer

Jul 15, 2025

·

Stayed 1 night

The staff was amazing. The room was clean and quiet. Our flight was cancelled so we needed a room quickly. The staff gave us a room that was ready hours before check-in. Great service, great location.

4

Sean

Apr 18, 2025

·

Stayed 1 night

Small, dirty little place. But, the kicker is that they use real keys that aren’t stamped with room number all that well. This was a problem because the guy at front desk gave us 2 keys to our “room” but one was the wrong room. After it wouldn’t open the one that was actually our room, we went to what the key said (thinking the front desk guy messed up) and yup, key worked…..let my wife open up a room with another couple having sex. The guy at the front desk just said “oh sorry” and gave us a better key. So no, we didn’t feel safe in these rooms as who knows who may just walk in.

6

Gerald

Jul 25, 2025

·

Stayed 1 night

Staff was unaccommodating at check-in to let us know what side of the property our room would be so we could carry our luggage to that part of the property

10

Susan Diana

Nov 10, 2024

·

The check-in process was very easy management was excellent to work with they gave me many tips on places to go and things to do. Thank you Carlos

6

Tequesta

Jun 20, 2025

·

Stayed 3 nights

Location is excellent. Property needs updating especially if they are charging the same rates as fees as surrounding hotels. The check in lady was very rude. Looks like she wanted to go home and busy speaking to others instead of completing my check out. The AC unit in the room barely blew cold air and when we said something they brought us a fan.

10

Jody

Feb 23, 2025

·

Stayed 2 nights

I cannot say enough good things about this motel. Karen, at the front desk was so helpful. She gave us tons of recommendations and was very accomodating. We parked our car and didn't have to move it until we left Key West. We walked to the beach, Southernmost Point, Bars, Restaurants, Hemingway House and Mallory Square. We would definitely stay here again.

10

Melissa

Sep 25, 2025

·

Stayed 4 nights

Hotel is amazing has everything you need. Pools are clean. Service is amazing

8

Denise

Sep 9, 2025

·

Stayed 1 night

Great location. Place was clean and neat. Leary about motels but this one was very nice. Didn't get to use all the amenities. Would suggest.

Was this helpful?

AI-generated summary based on recent guest reviews

Location

Excellent, walkable base near the quieter end of Duval Street, Southernmost Point, beaches, and trolley/loop stops. Easy access to restaurants, bars, and attractions without needing to drive.

Related guest reviews

8

Maximo

Jun 17, 2025

·

Stayed 4 nights

Great location close to everything around old town key west

10

Bruce T

Apr 9, 2025

·

Stayed 3 nights

Very clean and very convenient to get to the beach and Duvall. Perfect location. We'll definitely stay again!

10

Perry

Oct 16, 2025

·

Stayed 2 nights

Perfect location for everything in Key West.

10

Jodi

Feb 26, 2025

·

Stayed 4 nights

Location, location, location! We were very well pleased with everything. The staff was super friendly and helpful!!! Rooms were very clean, and the place had all the amenities we could ask for! Definitely will stay there again and highly recommend SouthWinds to others.

10

Linda

Jun 24, 2025

·

Stayed 1 night

The location was perfect! Everything is right there, it's safe and the staff was wonderful!

10

Anne-Marie

May 20, 2025

·

Stayed 2 nights

Close to the beach!

10

Lisa

Jan 21, 2025

·

Stayed 2 nights

Location location location Property is a block away from Duval St Walked everywhere

10

Nicole

Oct 15, 2025

·

Stayed 3 nights

Great place!! Centrally located to be able to walk all over and check out the Duval Street area. Suited our needs perfectly.

10

James

Jun 30, 2025

·

Stayed 2 nights

Great location. Good value, small rooms because they have updated a motel from a past era. Friendly helpful staff. Laundry room was a plus.

8

Varun

Jul 28, 2025

·

Stayed 1 night

The Motel has been well maintained and the staff are very helpful. Location is great.

Was this helpful?

AI-generated summary based on recent guest reviews

Dining

The complimentary continental breakfast is basic and cold (muffins, cereal, yogurt, fruit); some find it convenient, others find it limited. The Tipsy Rooster bar with live music is a popular on‑site option.

Related guest reviews

8

Linda

Mar 11, 2025

·

Stayed 4 nights

The check in process was easy. The property offers 2 pools,( 1 smaller heated one) which are clean, and a very basic continental breakfast with several comfortable outdoor areas. Unfortunately, maid service is only every 3 days, but we had to specifically ask for our room to be done because our room was not initally on the list for our 3rd day there. The room, itself, is clean, but is a very, very dated room with a tiny bathroom, though the bed is comfortable. The location is great and musical entertainment is offered daily as part of the complex, along with outdoor bar and pricy ice cream truck. The Cuban restaurant across the street is casual and delicious. The staff are very helpful and friendly.

8

francesca

Nov 20, 2024

·

Stayed 1 night

a good location for one night. breakfast included with pre-packaged food. umbrella and chair in the beach included in the fee.

10

Brenda

Nov 18, 2025

·

Stayed 7 nights

Yes,breakfast was fresh.

10

Randy

Jan 11, 2024

·

Stayed 2 nights

Location on the southern part of old town was perfect. Biked to everywhere. Groceries across the street. Rooms are small and have been around for a while. But they were clean.

10

mark

May 18, 2025

·

Stayed 1 night

Fantastic location Friendly staff. Has a decent pool. Really good breakfast ( wasn’t hot but still had excellent choices) There is a bar next door which has a singer on at various times Overall really good option

6

Linda

Nov 12, 2025

·

Stayed 2 nights

Room is very small with nowhere to put things. However it was clean. Excellent location for walking all around key West. Breakfast was small.

6

Barry

Oct 25, 2025

·

Stayed 3 nights

Tiny rooms. Tiny TV. The bathroom is so small you can’t even close the door while sitting on the toilet. The breakfast was just a counter with some packaged muffins, yogurt packs, packaged eggs.

10

stephen

May 19, 2024

·

Stayed 3 nights

Had an amazing time at this property. Everyone was so kind and helpful and help me navigate (dining, excursions, scooters, etc). Great bar, live music and continental breakfast. I was disappointed when they asked for an additional $67 after arriving seeing I thought all cost were covered...it's for daily breakfast. Anyway, one small thing out of my WHOLE visit. Definitely would stay with these guys next time.

8

Ronny

May 6, 2025

·

Stayed 3 nights

Loud air conditioner from the room across, clean but simple, friendly staff, very basic pre-packaged breakfast.

8

Daile M

Sep 13, 2025

·

Stayed 2 nights

As far as key west is concerned, this is a great budget hotel and easy walking to most places touristy. We based our stay here on using the e scooters on site to get around and had all kinds of issues which was unfortunate. The breakfast included was great. I do have an odd charge to follow up on with the hotel

Was this helpful?

AI-generated summary based on recent guest reviews

Month	Average price
January	$313
February	$376
March	$361
April	$305
May	$235
June	$167
July	$162
August	$147
September	$131
October	$205
November	$227
December	$246

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15	16 $128	17 $122	18 $150	19 $153
20 $121	21 $122	22 $130	23 $130	24 $130	25 $177	26 $160
27 $130	28 $130	29 $130	30 $135

Su	Mo	Tu	We	Th	Fr	Sa
				1 $150	2 $183	3 $202
4 $171	5 $138	6 $150	7 $163	8 $181	9 $242	10 $230
11 $193	12 $150	13 $151	14 $175	15 $186	16 $295	17
18 $339	19 $344	20 $328	21 $418	22	23	24
25 $193	26 $180	27 $190	28 $182	29 $202	30 $285	31

Select dates to see prices and availability

Monthly average prices

About this property

Location

Room options

Standard Queen Room

Queen Room with Two Queen Beds

Queen Deluxe

Standard King Room

Guest reviews

Very good

Who stays here?

What guests think

Property Policies

Check-in instructions

Good to know

FAQs about Southwinds Motel

Have a question?

Considering this hotel for your Key West trip?

Prices for upcoming dates