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 96 Key West B&Bs / inns

Southwind Motel

2.0 of 5 Small Hotel   |   1321 Simonton Street, Key West, FL 33040
Hotel amenities
Southwind 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 1 more site!
Save Saved
You added Southwind Motel to your Saves list
Ranked #71 of 96 Key West B&B and Inns
A recent review
Write a Review

73 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 (17)
Date | Rating
  • English first
  • German first
  • Italian first
  • Portuguese first
  • Any
English first
  • All months
  • Mar-May only
  • Jun-Aug only
  • Sep-Nov only
  • Dec-Feb only
All months
3 reviews 3 reviews
4 of 5 stars Reviewed 3 days ago NEW

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
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
New York City, New York
4 reviews 4 reviews
4 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed April 2, 2014

Basic motel type facility - no frills but worth the price - location is fabulous. Staff were very nice and accommodating. Loved the quietness and the location to the beach was terrific - just walked down the block and a short walk to Duval.

Was this review helpful? Yes 1
Orlando, Florida
1 review
1 helpful vote 1 helpful vote
3 of 5 stars Reviewed March 23, 2014

This was a nice clean lower priced hotel. I would have definitely recommended this Motel if it were not for the beds. We had four people in a room with two beds. Both beds squeaked all night long, anytime one of us moved. We could have dealt with the fact that the were hard and not very comfortable but the... More

Was this review helpful? Yes 1
5 reviews 5 reviews
7 helpful votes 7 helpful votes
3 of 5 stars Reviewed March 10, 2014

This is an old Florida motel in a great location right at the southernmost point. It is well kept with most of the basics. Price was reasonable compared to other properties in Key West. None of the musty smell usually found in old motels. Ample free parking is a bonus in Key Wet. Bob at the desk was polite and... More

Was this review helpful? Yes 2
Key West, Florida
1 review
5 of 5 stars Reviewed March 5, 2014

We stayed here on March 4,2014 and found the room to be very clean and nice. Its basic but it was worth what we paid the lady at the front desk had character and was the nicest lady. We had a little kitchen area and plenty of space but what was so nice in this place was it was close... More

Was this review helpful? Yes
18 reviews 18 reviews
5 hotel reviews
17 helpful votes 17 helpful votes
5 of 5 stars Reviewed March 3, 2014

We have stayed many places in KW, and we'll be back here again! It's a hidden gem. Nothing fancy-resortish, but all the basics and a great location. Nice pool, large, clean rooms, refrigerator, ample & free (unusual in KW) off-road parking. 20 minute walk to Mallory Square, 5 minute walk to Southernmost point & closest beach. Great Cuban walk-up restaurant... More

Was this review helpful? Yes 2
Fort Lauderdale, FL
20 reviews 20 reviews
9 hotel reviews
22 helpful votes 22 helpful votes
3 of 5 stars Reviewed February 19, 2014

This is an inexpensive motel in Key West and a block off Duval. Was it amazing? No. It was fine...had the basics and we spent very little time there. It was clean but smelled a bit musty (could have been the A/C). We were forced to find a room when our existing reservation got cancelled elsewhere. I would stay here... More

Was this review helpful? Yes 1
Cleveland, Ohio
4 reviews 4 reviews
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed February 14, 2014

So glad we stayed at the Southwind Motel in February 2014. Newly renovated rooms and clean, clean, clean! We were in #7, right beside the pool- which again- is super clean. Linda at the front desk is a sweetie and gave us several suggestions for dining. Great location and easy to walk to everything. Quiet and the grounds are very... More

Was this review helpful? Yes 2
Top Contributor
79 reviews 79 reviews
38 hotel reviews
54 helpful votes 54 helpful votes
4 of 5 stars Reviewed February 5, 2014

I gave this motel 4 stars for several reasons. We are in room 6 which was just completely renovated. For my comfort, the mattress needs to be replaced. There is 1 bed as you walk in with a table for two (three if someone sits on the bed and eats) & a kitchenette. There is a door that slides into... More

Was this review helpful? Yes
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 Southwind Motel? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Southwind Motel

Address: 1321 Simonton Street, Key West, FL 33040
Location: United States > Florida > Florida Keys > Key West
Price Range (Based on Average Rates): $$
Hotel Class:2 star — Southwind Motel 2*
Number of rooms: 18
Reservation Options:
TripAdvisor is proud to partner with Expedia, Hotels.com, Venere and Despegar.com so you can book your Southwind 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

4 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (5)
Other (5)
Hotels you might also like...
Check In Check Out
Price Your Stay