Members-only rates
4.1 / 5 Great

Southwinds Motel

Southwinds Motel
Southwinds Motel – Key West, FL
Southwinds Motel – Key West, FL
Check in 4:00 PM
Check out 11:00 AM

About Southwinds Motel

Offering 2 outdoor pools, this Old Town Key West motel features high-speed WiFi access and a cable TV in each room. Duval Street is 2 minutes' walk away. All rooms include a microwave, refrigerator, hair dryers, and plush eurotop mattresses. Extras include daily continental breakfast, convenient bicycle on-site, beach access, and our Tipsy Rooster Bar and Liquor Store. A concierge desk and luggage storage are available at Southwinds Motel. Parking is available on-site. Laundry facilities is also at the property. The Ernest Hemingway Home and Museum is 12 minutes' walk away. Guests at the property can rent bicycles to explore the area. Fort Zachary Taylor Historic State Park is less than 2 mi away.

Amenities

  • On-site parking
  • 24-hour front desk
  • On-site dining
  • Bar / lounge
  • Café / coffee shop
  • Express check-in / check-out
  • Concierge
  • Dry cleaning
  • Self-service laundry
  • Luggage storage
  • Multilingual staff
  • Pool
  • Smoke-free property

Reviews

4.1 / 5
Great 2203 reviews
  • Engine customer Aug 2026

    Exceptional

  • Engine customer Aug 2026

    This was day 16 of a US road trip and this was BY FAR my favorite stay. 1 block away from Duval St. Free drink tickets. Great bed and pillows. Microwave, fridge. Everything was GREAT! Only downside was we went to bed at 10 and the nearby bar was still playing loud live music, however the loud AC unit drowned it out lol. Ice machine could use something to make it look cleaner/better, but still produced ice just fine. Breakfast was pretty much entirely bread/muffins/cereal/bagels. Parking was not free, which is also a bummer. But being so close to everything we wanted made up for it.

  • Engine customer Aug 2026

    Great location and the Tipsy Rooster bar attached to the property is an awesome bar!!

  • Engine customer Aug 2026

    Friendly staff, clean rooms and property with an old school feel. We enjoyed our stay and will return.

  • Engine customer Aug 2026

    Should do a better job of keeping the outdoors clean.

  • Engine customer Aug 2026

    We stayed one night with my parents, it was awesome, and the were really kind and helpful. Only a 15 min walk from the Duval Street center. We liked this accommodation a lot.

  • Engine customer Aug 2026

    Duty

  • Engine customer Aug 2026

    The staff was very nice. The location was good. It was a good price. The breakfast was OK. Our room is on the small side, but the bed was very comfortable. It was weird. We had no cold water. Yes, the property is dated and it was a little bit too quiet for my liking. and also the beach we could not use the beach and no one told us until we got there. There was a stair was all seaweed washed up on the beach and it smelt very bad.

  • Engine customer Aug 2026

    The staff were great and were very helpful The smell of our room. Not sure what it was but it wouldn’t go away. It was BAD. They moved us rooms and tried to help but that room was bad as well.

  • Engine customer Aug 2026

    I didn’t finish my stay after I complaint cockroach in bathroom I checked out next day I didn’t get my refund for the 2 days I have invoiced mentioned I deserve refund I submitted complaint in booking without any progress

  • Engine customer Aug 2026

    KAREN (real first name - haha), the front desk manager, was absolutely WONDERFUL! She went way beyond the usual expectations to make our stay enjoyable. A full sized coffee maker with ample supplies was greatly appreciated and needed! Disappointed that there was not daily housekeeping but that was a minor inconvenience.

  • Engine customer Aug 2026

    Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location.

  • Engine customer Aug 2026

    Room was clean and the staff was very helpful. Location of motel was very convenient to get to Duval street

  • Engine customer Aug 2026

    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.

  • Engine customer Aug 2026

    Good

  • Engine customer Aug 2026

    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!

  • Engine customer Aug 2026

    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.

  • Engine customer Aug 2026

    Perfecto!! Muy cómodas las habitaciones, las camas y todo muy limpio. Desayuno bien, cumple con u continental ofreciendo café, jugos, huevos, yogur, cereales y pan con manteca o queso. Piscinas ok. Todo funciona muy bien Ubicación buena a pesar q el sargazo nos obliga a ir hacia el otro lado del Cayo. Nothing

  • Engine customer Aug 2026

    Everything was excellent When I checked in, everything was perfect the day I went to check out my deposit was short come to realize I was charged for parking after booking.com. Said everything was paid for when I explained to them the problem. They basically did not care and told me to boogie.com and I showed them all the receipts and paperwork they did not care it’s sad cause I really love this property and I go every other month down to Key West

  • Engine customer Aug 2026

    Air con was amazing. The bar table area was very useful. Larger TV would have been great!

Frequently asked questions about Southwinds Motel

Does Southwinds Motel have free Wi-Fi?
Wi-Fi could be available but may carry a charge. Confirm with the property before booking.
Does Southwinds Motel offer parking?
Yes, paid self-parking is available on-site at Southwinds Motel.
Does Southwinds Motel have meeting spaces, conference centers, or conference rooms?
Southwinds Motel does not list dedicated meeting or conference facilities. For business event venues in Key West, see business hotels in Key West.
Does Southwinds Motel have a fitness center?
Southwinds Motel does not list an on-site fitness center. Some properties partner with nearby gyms — check directly with the hotel.
Where is Southwinds Motel located, and how walkable is the area?
Southwinds Motel is located at 1321 Simonton Street, Key West, FL 33040. With a Walk Score of 91, the area is rated Walker's Paradise. Most daily errands can be done on foot — ideal for travelers without a car.

What's nearby

Map of points of interest near Southwinds Motel
  • Key West Airport 2.6 mi

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