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 Sep 2026

    It was small and old fashioned, but it had an old Florida vibe that we loved. Everything we needed was there. The staff were very helpful.

  • Engine customer Sep 2026

    Rooms were clean. Staff were very helpful. The pools were eh decently clean but they had some dirt

  • Engine customer Sep 2026

    Great location. Nice pool. Parking. Thirsty Rooster 🐓 bar out front was so much fun and a great vibe. Not to mention a close distance to Duval St. Where the action is. Deli and groceries across the street as well. We will be back

  • Engine customer Sep 2026

    What a cute place! I always try to stay at local places over chain hotels and this place did not disappoint! The staff was super friendly and helpful. The continental breakfast gave plenty of options: boiled eggs, yogurt, cereal, juices, muffins, bagels, fruit and coffee. There are tables and hammocks outside to enjoy. The bar/liquor store attached is also really cute! Great drinks and live music every day set the island vibe. The location is perfect for meandering around Key West. I can't wait to come back!

  • Engine customer Sep 2026

    So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW

  • Engine customer Sep 2026

    Perfect spot

  • Engine customer Aug 2026

    Good food

  • Engine customer Aug 2026

    Enjoyed the stay, still a great location, experience, and value.

  • Engine customer Aug 2026

    It was very convenient to a lot of the main area. The staff was very nice and helpful. Love the company of chicken's and Iguana's for my morning coffee. The bathroom was a little small. Other than that, nothing.

  • Engine customer Aug 2026

    Exterior doors of out building falling apart seen down walkway. Breakfast choices ok.

  • Engine customer Aug 2026

    Very good

  • Engine customer Aug 2026

    Exceptional

  • Engine customer Aug 2026

    It is a great location. Close to many restaurants, shops, etc.. They have a bar/liquor store and live music every day.

  • Engine customer Aug 2026

    Exceptional

  • Engine customer Aug 2026

    Nice little property, and great location!

  • Engine customer Aug 2026

    We enjoy staying at Southwinds for short getaways. It’s an Old Key West feel with the fun Tipsy Rooster

  • Engine customer Aug 2026

    I liked that there was a rug under the bed, the water heater worked well, the shower was big, the air worked great, the bed was comfortable, the little fridge came in handy, the pools were great, the location was good and walkable to lots of stuff. Enjoyed the music and the little bar right there. The little grocery store across the street came in handy too. Needed more shelves in the shower, needed more hooks for towels in the bathroom, the water pressure was not good, the gutter needed fixed right outside the door. The biggest thing is we needed some black out curtains for the window there were two big lights out in front of it and it was very bright at night in the room. Thank goodness for towels and hair clips.

  • 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!!

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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