We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
All 43 Key West hotels

Southwinds Motel

2.0 of 5 Motel   |   1321 Simonton Street, Key West, FL 33040
Hotel website
Hotel amenities
Offers & Announcements
10% off room rate
Southwinds Motel
Best prices for your stay
Enter dates for best prices
Check In Check Out
Show Prices
Compare best prices from top travel sites
and 5 more sites!
You added Southwinds Motel to your Saves list
Ranked #38 of 43 Hotels in Key West
A recent review
Write a Review

276 reviews from our community

Traveler rating
See reviews for
Rating summary
  • Location
    4 of 5 stars
  • Sleep Quality
    3.5 of 5 stars
  • Rooms
    3.5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    4 of 5 stars
  • Cleanliness
    4 of 5 stars
Traveler tips help you choose the right room.   Room tips (33)
Date | Rating
  • English first
  • French first
  • German first
  • Italian first
  • Japanese first
  • Portuguese first
  • Russian first
  • Spanish first
  • Swedish first
  • Any
English first
  • All months
  • Mar-May only
  • Jun-Aug only
  • Sep-Nov only
  • Dec-Feb only
All months
3 reviews 3 reviews
1 helpful vote 1 helpful vote
4 of 5 stars Reviewed 5 weeks ago

Undergoing somewhat of a reno or "facelift" as they called it. New name, fresh paint, landscaping, etc. Is now conjoined with the motel next to it. That gives you access to a second, larger pool as well as laundry facilities. As during the prior stay, rooms were clean and neat. AC worked like a champ. Friendly staff. Huge local bakery... More

Was this review helpful? Yes 1
Guildford, United Kingdom
Senior Reviewer
9 reviews 9 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
4 of 5 stars Reviewed August 21, 2014 via mobile

We were due to stay only 3 nights in the Ocean Breeze but extended by 2 more as it was the cheapest accommodation during our stay and it was very comfortable! The kitchenette was a massive bonus! And the air con worked great! The location was fab and the staff were helpful at all times! Yes it's a little rough... More

Was this review helpful? Yes 2
Tampa, Florida
Senior Contributor
25 reviews 25 reviews
6 hotel reviews
13 helpful votes 13 helpful votes
1 of 5 stars Reviewed August 15, 2014

I am all about quaint and charming, but this place is not quite on that level. I read reviews and based on a lot of LGBT reviewers assumed that this place was a hidden gem. NOPE. We were moved to a different room than we booked, which was called an upgrade, but it was across the street from the main... More

Was this review helpful? Yes 2
5 reviews 5 reviews
4 hotel reviews
3 helpful votes 3 helpful votes
3 of 5 stars Reviewed August 12, 2014

Great hotel for a quick trip to Key West. We didn't spend much time in our room, so the hotel immenities were not that important to us. This is an older hotel but so are 90% of the hotels in Key West. Our room was clean but yes as indicated in prior posts could use major updating. Cracked plastered walls,... More

Was this review helpful? Yes
Springfield, MO
Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
1 of 5 stars Reviewed July 25, 2014

Old and run down. Needs Major overhaul!!! Continental bkfst not up til 8:30. There is a bldg behind their other property across street that is covered and "Keep Out, Poison" signs on it. We had to leave a day early and NO help with any refund. There are MANY other places close by that are much better. Spend your time... More

Was this review helpful? Yes 2
Islamorada, Florida
19 reviews 19 reviews
11 hotel reviews
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed July 21, 2014

First of all Heather the manager is an avid cyclist and went over backwards to help us get rooms this past Saturday Night. Key West was packed, everybody wanted 2 and 3 night minimums. We got our room for one night after our 100 mile bike ride and they were comfortable and clean. Loved the pool and the location was... More

Was this review helpful? Yes
Guin, Alabama
Senior Contributor
47 reviews 47 reviews
13 hotel reviews
25 helpful votes 25 helpful votes
2 of 5 stars Reviewed July 9, 2014

So we had to just find somewhere we could sleep to 1st night. Now,,, I know should book before we gone down here. But we wanted to find something to our taste and fit our budget. But over all I don't wouldn't stay here again. The pictures what's show on this website is somewhat not the same. Perhaps 12 to... More

Was this review helpful? Yes
Mt Dora, FL
Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
2 of 5 stars Reviewed June 17, 2014

This place could be so cute; it has all the right ingredients, but they didn't spend any money on decorating--what a waste. The beds were hands down the worst we have ever slept on--they have nerve offering these at any price--they are not even good enough to donate to charity. The location is great and the staff--particularly Tatiana--is wonderful. They... More

Was this review helpful? Yes
Senior Contributor
27 reviews 27 reviews
29 helpful votes 29 helpful votes
5 of 5 stars Reviewed June 7, 2014

This was an old historic house. We stayed in IBIS room that was right next to the Jacuzzi. It was very quiet no problems. This room had a king size bed, it was very clean and well kept. I will say bring some walking shoes if you plan to walk the length of Duval st. We had fun at the... More

Was this review helpful? Yes
Portland, Oregon
11 reviews 11 reviews
5 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed April 27, 2014

Really enjoyed my five nights at Southwind this past year. Great French cafe, beach restaurant(with beach), and scooter rentals very near the hotel. We are still talking about this trip to KW in part because of our great stay at Southwind. Until next time!

Was this review helpful? Yes 1
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
Manage your listing

Been to Southwinds Motel? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Southwinds Motel

Address: 1321 Simonton Street, Key West, FL 33040
Phone Number:
Location: United States > Florida > Florida Keys > Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Southwinds Motel 2*
Number of rooms: 32
Reservation Options:
TripAdvisor is proud to partner with Hotels.com, Booking.com, Expedia, Priceline, Venere, Travelocity, Odigeo and Despegar.com so you can book your Southwinds Motel reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
Also Known As:
Southwind Hotel Key West

88 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (76)
Pool/beach area (15)
Room/suite (23)
Hotel & grounds (10)
View from room (2)
Dining (2)
Other (24)

Management photos: Courtesy of the property manager

All management photos (13)
Hotel & grounds (6)
Room/suite (5)
Dining (1)
Other (1)
Hotels you might also like...
Check In Check Out
Price Your Stay