About this property
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 and e-scooter rentals 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.
Couples in particular like the location – they rated it 9.3 for a two-person trip.
Distance in property description is calculated using © OpenStreetMap
Most popular amenities
- Outdoor swimming pool
- Private Parking
- Wifi in all areas
- Non-smoking rooms
- Bar
- 24-hour front desk
Guest reviews
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Guests who stayed here loved
- Costa
United States
“All in all good location, nice atmosphere. Like where we were in room 70. If return room 71 would be nice - like the porch. Staff were friendly and welcoming. Thank you for a nice stay.” - Cheryl
United States
“Basic breakfast. Small bathroom which was ok. Loved the tipsy rooster out front” - Denise
United States
“Very comfortable beds & pillows. Great location” - Terri
United States
“Very clean. Very comfortable bed! Pools were both very nice. Staff is extremely friendly and helpful. Close to the Southern most point. Lots of parking.” - Eitan
Israel
“Nice location Friendly staff Nice bar and ice cream on site” - Karly
United States
“I have been staying at Southwinds for over 10 years when I come to Key West. It's a great location! I either rent a golf cart or trailer my LSV down with me. The whole entire staff is very friendly (guest services, housekeeping, and...” - Bill
United States
“location was very nice. nice continental breakfast and friendly staff” - Brian
United States
“Reasonable price, great location, friendly staff, room facilities were good, continental breakfast was good...all around pleasant experience!” - Karin
United States
“Great motel on the quieter end of the island. We loved the feel of it—the pools, free laundry, free breakfast, Tipsy Rooster bar. Has everything you need at a good price. We spent a bit more to get a room with two beds so we had more space. Retro...” - Marie
United States
“Location was excellent for the event I was attending (very close to the Southernmost point.) Room was clean with lots of outlets and a desk. Enjoyed the free juice all day in the lobby. Enjoyed the outside seating out front (but more shade would...”
Area info
House rules
Child policies
Children of all ages are welcome.
Children 18 and above will be charged as adults at this property.
To see correct prices and occupancy info, add the number and ages of children in your group to your search.
Crib and extra bed policies
Cribs and extra beds aren't available at this property.





The fine print
Guests under the age of 18 can only check in with a parent or official guardian.
Please note that the resort fee includes:
- Parking
- Wireless Internet
- Beach Access
- Lounge Chairs
- Towels
Please note the breakfast included rate includes a complimentary continental breakfast.
Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
In response to the coronavirus (COVID-19), additional safety and sanitation measures are in effect at this property.
Food and beverage services at this property may be limited or unavailable due to the coronavirus (COVID-19).
Due to the coronavirus (COVID-19), this property is taking steps to protect the safety of guests and staff. Certain services and amenities may be reduced or unavailable as a result.
A damage deposit of $150 is required on arrival. This will be collected by credit card. You should be reimbursed on check-out. Your deposit will be refunded in full by credit card, subject to an inspection of the property.