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1321 Simonton St, Key West, FL 33040-3113
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COVID-19 update: See the added health and safety measures this property is taking.Read more
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Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (434)
Room & Suite (95)
Pool & Beach (30)
Travel safe during COVID-19
What you can expect during your stay
  • All linens sanitized in high-temperature wash
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Hand sanitizer available to guests & staff
  • Regularly sanitized high-traffic areas
  • Staff required to regularly wash hands
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Updated 06/25/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Southwinds Motel
Updated 06/25/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.

About

#26 of 51 hotels in Key West
Location
Cleanliness
Service
Value
Travelers' Choice
Clean affordable motel rooms only 1 block from Duval Street at the Southernmost point of the Island of Key West. Many restaurants and shops within walking distance.
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Full view
Property amenities
Free parking
Free High Speed Internet (WiFi)
Pool
Free breakfast
Bicycle rental
Baggage storage
Non-smoking hotel
24-hour front desk
Street parking
Wifi
Pool / beach towels
Outdoor pool
Outdoor furniture
Sun loungers / beach chairs
Laundry service
Self-serve laundry
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Room features
Air conditioning
Housekeeping
Microwave
Refrigerator
Flatscreen TV
Room types
Non-smoking rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Centrally Located
Languages Spoken
English, Russian, Spanish, Latvian
1,497Reviews42Q+A100Room tips
Traveler rating
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Popular mentions
Stephen C wrote a review Nov 21
2 contributions
From the time that we arrived until we left all of the employees at the front desk and also housekeeping were very friendly and accommodating. The room was small but very clean and well put together and worked well for my wife and I as we had great weather and didn't want to waste it in our room. The grounds were very clean and well maintained and somewhat picturesque with all of the well groomed foliage. We enjoyed the location which was maybe a mile from all of the tourist area so it was more relaxed. All in all my Wife and I were very pleased with the Southwinds Motel
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Date of stay: November 2020
Value
Cleanliness
Service
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Response from James Heineman, Owner at Southwinds Motel
Responded 2 days ago
Dear J2346WHstephenc, Thank you so much for taking the time to write this great review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. We have many superstars on our team that are dedicated to providing great guest service. We believe we have some of the best amenities and by far the best staff that makes our motel so special. We look forward to hosting your next trip and thanks for telling your friends as well! All the best, Jim Heineman VP Operations
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Matt B wrote a review Nov 17
16 contributions8 helpful votes
The entire time I was in Key West, I was wondering to myself "How WOULD I review this place?" On the one hand: The price was right, the location was good (not great, as a lot of the "touristy" areas are on the North End of the island) and the bedding was surprisingly comfortable. On the other hand, since I figured this was a ‘bargain motel’ kinda place, I'd ‘pop’ for the biggest room, which was large, with two Queen beds, but I found it lacking in several regards: The “area that almost looked like a kitchenette” (I refuse to call it a kitchenette, because while it DID have a countertop with four kitchen stools, a coffee maker, microwave and small refrigerator) it did NOT have any plates, glasses, utensils or anything else one might find in a kitchen or kitchenette. It didn’t even have any drawers in which to put these things if it DID have them. So while (as a Seasoned Traveler) I did bring my own bacon maker and egg poacher to use in the microwave, there was no dish soap, sponge or dishwasher, so … again … not a kitchen/ette. Not a problem, I thought, because another "nice" thing was that breakfast was included, and when I checked in, I did notice the breakfast "area" in the lobby, where I tried to keep a realistic expectation of what would be offered in the morning. The next morning I will admit that I was slightly disappointed to find out there were cellophane-wrapped muffins … and coffee … and juice. Which, again, is kinda nice (I mean, there were three different KINDS of muffin) but some cereal, or toast and jam or a package of instant oatmeal, or – perish the thought – a waffle iron, would’ve added immensely to the livability of the accommodations. Since we did buy our own breakfast fixins to eat in our room, it would’ve been nice to even have ACCESS to a toaster, but … no. So, while the room was clean (and the bedding …VERY comfortable) it lacked certain amenities one expects in a motel/hotel room. First, there was no programmable safe in the unit, which I generally take for granted when traveling. I had brought my work laptop, which, while not a very expensive model, has a LOT of confidential information on it, so leaving it in an unsecured environment caused me a fair amount of worry as I wandered about the island. Secondly, there was no room phone, which, I guess, really shouldn’t be such a surprise, since I don’t know ANYONE who actually has a landline phone anymore, but if you wanted to reach the front desk, you actually had to look up a phone number and dial it from your cell phone, so … yeah, it was a little inconvenient. Because there WERE issues we needed addressed: The exterior light by our door was out (and while we requested it be fixed at least twice, it remained out for the entirety of our five-day stay) and the refrigerator froze all our groceries solid (they DID replace the refrigerator the second day) Most hotel/motel rooms have some sort of a desk, or table and chairs which makes it easier to watch TV, especially while having breakfast or enjoying a drink at night. However, In opting to make our room “look like” it had a kitchenette, the Southwinds Motel opted for an immovable high counter affixed to the same wall from which the Television was mounted on a dresser. And while you could swivel the TV, and perch on a backless stool on the other side of the counter whilst eating your microwaved-but-non-toasted-breakfast-sandwich, a small table and chairs would have served the space much better and provided some much-needed functionality. The air conditioner was another matter entirely: It was a pretty noisy wall-mounted unit, and while the droning noise probably actually contributed to some of the very best sleep I’ve had in years (did I mention how comfortable the bedding was?) it also had a very gurgly watery sound, and could not be adjusted. Luckily, I was fine with “Arctic” and it was unbelievably humid while we were there, so at least there was a good reason it sounded like Paul Bunyan was gargling. The front desk staff was friendly and pretty good (would’ve been VERY good if they would’ve had that lightbulb replaced) and the “resort fee” was actually WORTH what we paid for it. Because in addition to having four small pools scattered about the various buildings (this obviously used to be several different businesses in years gone by) as a guest at the Southwinds, you were entitled to two beach chairs at the VERY nearby South Beach. (You could also take the Pool Towels to the beach.) And while South Beach is probably the smallest beach on the island, I would rather walk a block and lie on a Chaise lounge there than to hoof it a larger beach half a mile away and lie on a towel. It would have been VERY nice if the umbrella would’ve been included (there’s an extra charge of either $5 or $10 for the umbrella, depending upon which Eastern European Muscle Man is working the beach that day) but again, you get what you pay for, and at $22.50 per day, I found the resort fee to be pretty darn reasonable. Another welcome surprise was the bar/liquor store next door to the lobby. While you could buy packaged beer and wine at dozens of places, getting a bottle of Captain Morgan’s would have been harder to do had the “Tipsy Rooster” not been next door. In addition to package sales, the Tipsy Rooster features a walk-up bar with outdoor seating, a friendly bartender, and even had a pretty decent singer/guitarist playing his own reggae-influenced arrangements of past and present Top 40 hits on Friday night. (Rock On, Peter!) So, while it may sound like I emphasized the negatives over the positives, it’s only because I had a very NICE time here, when I COULD HAVE HAD a Fantastic Time. Would I stay here again? Yes. But I’d bring utensils, and I’d opt for a smaller room, one with tables and chairs.
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Date of stay: November 2020
Cleanliness
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Response from James Heineman, Owner at Southwinds Motel
Responded 4 days ago
Dear DeborahB3177, Thank you so much for taking the time to write this review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. We have made many changes to our amenities in our guest rooms and our breakfast program due to the COVID 19 pandemic to protect our staff and our guests. We hope that as the pandemic becomes under control we will be able to add some of the services you commented on back into place. We have many superstars on our team that are dedicated to providing great guest service. We believe we have some of the best amenities and by far the best staff that makes our motel so special. We look forward to hosting your next trip and thanks for telling your friends as well! All the best, Jim Heineman VP Operations
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cumberlandga wrote a review Nov 12
Fernandina Beach, Florida405 contributions93 helpful votes
We checked in late when Eta was on its way. Shara greeted us warmly from the start! We were so happy w/the location, the awesome customer service (Shara) & the room. The room was clean & equipped w/everything we needed. The grounds were beautiful w/all the flowers & shrubbery. Because of the storm we didn’t use the pools but they were clean & well maintained. I’m so glad I found this place, the three of us agreed, whenever we come back, we’ll be staying here!
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Date of stay: November 2020Trip type: Traveled with friends
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Response from James Heineman, Owner at Southwinds Motel
Responded 1 week ago
Dear cumberlandga, Thank you so much for taking the time to write this great review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. Shara is just one of the many superstars on our team that are dedicated to providing great guest service. We believe we have some of the best amenities and by far the best staff that makes our motel so special. We look forward to hosting your next trip and thanks for telling your friends as well! All the best, Jim Heineman VP Operations
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Timothy B wrote a review Oct 2020
Lithia, Florida16 contributions2 helpful votes
We stayed here October 20-25. The location is perfect. A block off Duval and 2 block from the Southern Most Point. The rooms are small but they are clean and neat. The pools are clean and well stocked. The motel has its own bar and that was also a great place to begin or end the night. We will definitely stay here again. Oh and free parking and no resort fee.
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Date of stay: October 2020Trip type: Traveled as a couple
1 Helpful vote
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Response from Jim Heineman, Owner at Southwinds Motel
Responded 4 weeks ago
Dear K6837OXtimothyb, Thank you so much for taking the time to write this great review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. We have many superstars on our team that are dedicated to providing great guest service. We believe we have some of the best amenities and by far the best staff that makes our motel so special. We look forward to hosting your next trip and thanks for telling your friends as well! All the best, Jim Heineman VP Operations
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Shannon Y wrote a review Oct 2020
Orlando, Florida2 contributions1 helpful vote
We loved this motel. It is perfectly located in a quieter location only a block from Duval. Parking is included in the room charge so that was nice not to worry about. The room was clean and quiet. My only complaint is that the bathrooms are SMALL. I'm 5'9" and could have used more shower space. Other that, great motel, staff, and location.
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Date of stay: October 2020Trip type: Traveled as a couple
1 Helpful vote
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Response from Jim Heineman, Owner at Southwinds Motel
Responded Oct 8, 2020
Dear 698shannony, Thank you so much for taking the time to write this great review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. We have many superstars on our team that are dedicated to providing great guest service. We believe we have some of the best amenities and by far the best staff that makes our motel so special. We look forward to hosting your next trip and thanks for telling your friends as well! All the best, Jim Heineman VP Operations
Read more
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PRICE RANGE
$169 - $345 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
southwind hotel key west
LOCATION
United StatesFloridaFlorida KeysKey West
NUMBER OF ROOMS
58
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Frequently Asked Questions about Southwinds Motel
Which popular attractions are close to Southwinds Motel?
Nearby attractions include Key West Butterfly and Nature Conservatory (0.1 miles), Tipsy Rooster Liquor Store & Bar (0.02 miles), and Alan S. Maltz Gallery (0.2 miles).
What are some of the property amenities at Southwinds Motel?
Some of the more popular amenities offered include free wifi, free breakfast, and a pool.
Which room amenities are available at Southwinds Motel?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What food & drink options are available at Southwinds Motel?
Guests can enjoy free breakfast during their stay.
Is parking available at Southwinds Motel?
Yes, free parking and street parking are available to guests.
What are some restaurants close to Southwinds Motel?
Conveniently located restaurants include Seaside Cafe at the Mansion, La Grignote, and The Lobster Shack.
Are there opportunities to exercise at Southwinds Motel?
Yes, guests have access to a pool during their stay.
Is Southwinds Motel located near the city center?
Yes, it is 0.5 miles away from the center of Key West.
Are any cleaning services offered at Southwinds Motel?
Yes, laundry service and self serve laundry are offered to guests.
Which languages are spoken by the staff at Southwinds Motel?
The staff speaks multiple languages, including English, Spanish, Russian, and Latvian.
Are there any historical sites close to Southwinds Motel?
Many travelers enjoy visiting Curry Mansion (0.9 miles), Harry S. Truman Little White House (0.9 miles), and Key West Garden Club (0.6 miles).