Facilities & services
Parking (additional charge)Designated smoking areaHousekeepingVending machineLaundry serviceConciergeTourist info deskMultilingual staffOutdoor Swimming poolFree breakfastWhere to?
Check-in/out dates
Select your dates
Guests and rooms
2 adults, 1 room
Find more hotels in Key West
Southwinds Motel 
1321 Simonton StreetSee mapHK$ 1,360.7per night
This is the cheapest price in 30 days, based on the rates on 1 Dec
Top reasons for booking
With a stay at Southwinds Motel in Key West (Old Town Key West), you'll be steps from South Beach and 3 minutes by foot from Duval Street. This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.
Popular facilities
Bar
24-hour front desk
Luggage storage
Exploring the area
Key West International Airport, 3.8km, About 7 mins from hotel by car
South Beach, 200m, About 3 mins from hotel by footNancy Forrester's Secret Garden, 200m, About 4 mins from hotel by foot6
Standard Room, 1 Queen Bed
1 double bed or bigger
23.0 m²
6
Deluxe Room
2 beds
28.0 m²
8
Standard Room, 1 King Bed
1 double bed or bigger
28.0 m²
6
Standard Room, 2 Queen Beds
2 beds
37.0 m²
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Reviews
Read all reviews
4.3/5.0
Great
1K+ reviewsLocation
0.0
Services offered
4.5
Cleanliness
4.1
Atmosphere & facilities
4.2
Reviews summary
From real reviews, powered by AI
All
4.5+
3.0+
Reviewed: 11 Aug 2026
1.0/5.0
Below averageStayed with friends
Old and worn out! Many physical and administrative issues. Also, extreme fees that were unknown until we arrived. We did not save money (as we thought) by using Expedia! Lots of detailed problems I won’t get into now, just don’t book a room at Southwinds in Key West.
Reviewed: 9 Aug 2026
5.0/5.0
FantasticStayed with kids
Nice spacious room. You get many coupons for nearby bars. You even get 1 free alcoholic drink from their Bar "Tipsy Rooster" :) We also ordered a golf cart through our motel's receptionist - and it was delivered to the motel. Location is a bit far from all the action of Duval St. But about 25 min walk to Sloppy Joe's. Still close enough NOT to drive :) Good motel for the money and amenities!
Reviewed: 9 Aug 2026
5.0/5.0
FantasticStayed with partner
We stayed from Thursday through Saturday. From the moment we arrived till we left we had the most wonderful experience. The staff was amazing. Everyone was helpful friendly. The room was a perfect size for 2 of us. It was cold, clean and ready when we got there early. We are already planning next year's trip and will stay here again but for an extra day. Kristen at the Tipsy Rooster bar which is attached to the motel was such a nice person. She is in the profession for sure. We had a great time with her. The music was great and the people we met there we had such a good time with. It was my first time in Key West but will not be my last. See you soon Southwind's.
Reviewed: 8 Aug 2026
4.0/5.0
GreatStayed with kids
Old School Cool! Great location and close to many amenities including golf cart rental!
Air con was amazing. The bar table area was very useful. Larger TV would have been great!
Reviewed: 3 Aug 2026
3.0/5.0
Good 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.
Reviewed: 2 Aug 2026
4.0/5.0
Great Good place!
Reviewed: 2 Aug 2026
2.0/5.0
Below average 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
Reviewed: 2 Aug 2026
5.0/5.0
Fantastic 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.
Reviewed: 1 Aug 2026
4.0/5.0
Great Great location. Friendly and helpful staff. Good breakfast. Small, dated room.
Reviewed: 31 Jul 2026
4.0/5.0
Great Good location and price.
Overview
Exploring the area
Transport
Key West International Airport
Attractions
South Beach
Nancy Forrester's Secret Garden
Simonton Beach
Southernmost Point of the Continental U.S.A.
Conch Train Tour
Key West Lighthouse and Keeper's Quarters Museum
Ernest Hemingway Home and Museum
Key West Snorkeling Tours
Parking (additional charge)Designated smoking areaHousekeepingVending machineLaundry serviceConciergeTourist info deskMultilingual staffOutdoor Swimming poolFree breakfast