Southwinds Motel

Recent Reviews: 1720

• User:kashgo

  Trip type: Couples

  Convenient and clean

  17 Mar 2026

  Nice place to stay in a central location. We were able to walk to duval street and beyond. Most sights are within walking distance. The hotel turned out to be fine and we were happy with our room. A big plus was free parking. Our room was quiet and we were not disturbed by any street noise. Breakfast was adequate though simple. The price of the was better than comparable locations. James Heineman, General Manager at Southwinds Motel, responded to this review Dear kashgo,Thank you for taking the time to leave this 5 Star review of our motel. We are pleased to hear that you enjoyed your stay. Our team is committed to delivering exceptional service to ensure our guests have a pleasant and relaxing visit. Thank you for your feedback. We look forward to seeing you again soon.All the best, Jim HeinemanVP Operations

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• User:03458293

  Trip type: Couples

  Brads stay at Southwinds Motel

  13 Mar 2026

  The motel is nice except it has a few drawbacks. The water pressure is really bad. I have booked this Motel twice now. You can barely take a shower. The internet was ok most of the time. My wife's computer would not connect at all . Old password from previous visit froze in her Lap top. Friendly staff and good location a Plus James Heineman, General Manager at Southwinds Motel, responded to this review Dear 03458293,Thank you for your review. We are pleased to hear that you enjoyed your stay overall. Our team is committed to delivering exceptional service to ensure our guests have a pleasant and relaxing visit. Thank you for your feedback and we will have our IT team and maintenance team look at these items. We look forward to seeing you again soon.All the bestJim HeinemanVP Operations

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• User:Gina A

  Trip type: Couples

  Lipstick on a pig

  07 Feb 2026

  I booked Southwinds because of the reviews on TripAdvisor. Perhaps I'm naive, having never been to the Keys before, but never in my life have I paid $350 for a room that reminds me of a 1970s Motel 6 room. I appreciate the efforts they have made to make improvements to this old property... but, still...On a positive note: The location is hard to beat (one block off Duval Sr.) and it was relatively quietThe negative: When we stayed, it was the coldest it's been in the Keys in 45 years - and there is no heat in the rooms and no extra blankets. When I commented to the front desk, they really didn't seem to care. We found the staff, in general, to be not very friendly. The room is very small and the bathroom is so tiny you can barely close the door when sitting on the toilet. There is no closet. Normally, I would not really care about these things... if the cost was low. Mark B, General Manager at Southwinds Motel, responded to this review Dear afreil,Thank you for choosing Southwinds Motel for your recent visit to Key West. We deeply appreciate you taking the time to share your experience. We are glad to hear that our location, just a block from the heart of downtown Key West, was convenient for your vacation. However, we are saddened to learn that your stay coincided with cooler weather, which caused discomfort during your time with us. While Southwinds is an older, historic property, our team works diligently to maintain our rooms and ensure that our guests have an enjoyable stay. We strive for excellence, and we are disappointed to hear that we fell short of your expectations this time. Your feedback has been shared with our management team, as guest comments are extremely valuable to us and help guide our ongoing improvements. We hope to welcome you back on a future visit to Key West.Best regards, Sarah PietruszaComplex Front Office Manager

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• User:Harold W

  Trip type: Couples

  Lower your expectations

  27 Jan 2026

  Although all lodging in old town Key West is extremely expensive Southwinds takes the prize for giving less and costing more. Our room was the size of a walk in closet with no seating or room to place your luggage other than the bathroom. For this luxury we paid over $950 for two nights and that’s after they waved $67 a night for resort fee (a pool we didn’t use). They say you get what you pay for but that is far from the truth at Southwinds.Oh, it was clean. Mark B, General Manager at Southwinds Motel, responded to this review Dear Harold,Thank you for your review. I apologize that we did not meet your expectations. Our team strives to ensure our guests have a pleasant, relaxing stay; however, we unfortunately fell short in your case. We offer a variety of room styles and hope you will consider rebooking with us so we can deliver accommodations that exceed your expectations. Thank you for your feedback.Best regards,Mark Bibb Area General Manager

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• User:christyv2021

  Trip type: Couples

  Location, location, location!

  22 Jan 2026

  This was a last minute reservation for one night. Being in old town is nice and this place is close to restaurants and bars, altho somewhat overpriced as compared to the bigger places. Our room was small but clean. Bed was very comfortable. Our room faced the street and was next to an open air bar so it was a bit noisy into the evening. Staff were friendly and helpful. Mark B, General Manager at Southwinds Motel, responded to this review Dear christyv2021,Thank you for your review. We are pleased to hear that you enjoyed your stay overall. Our team is committed to delivering exceptional service to ensure our guests have a pleasant and relaxing visit. Thank you for your feedback. We look forward to seeing you again soon.Best regards, Mark Bibb Area General Manager

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