Southwinds Motel
1321 Simonton St, Key West, FL 33040-3113
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Avg. HK$1,053 /night, 9/15 - 9/16
HK$2,145
per night
HK$1,556
per night
HK$967
per night
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4.5
#1 of 2 motels in Key WestLocation
Cleanliness
Service
Value
Located in the heart of Old Key West, Southwinds Motel offers affordable, charming accommodations just steps away from Duval Street, the Atlantic Ocean, and many of the island’s most popular bars, restaurants, and attractions. Relax at one of our two outdoor pools, take advantage of our beach access complete with chairs and towels, and enjoy our daily continental breakfast while you explore everything Key West has to offer.
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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
Pool / beach towels
Outdoor pool
Fence around pool
Outdoor furniture
Sun loungers / beach chairs
Laundry service
Self-serve laundry
Room features
Air conditioning
Housekeeping
Iron
Wake-up service / alarm clock
Microwave
Refrigerator
Flatscreen TV
Room types
Non-smoking rooms
Good to know
HOTEL CLASS
Star ratings are intended to indicate the general level of features, amenities, and services to expect. This property is classified according to Giata.
HOTEL STYLE
Quaint
Mid-range
Languages Spoken
English, Spanish, Latvian
Location
1321 Simonton St, Key West, FL 33040-3113
Getting there
Great for walkers
Places to stay are graded on a 0-100 scale. The higher the grade, the easier it is for travellers to find restaurants and things to do within walking distance.
Grade: 93 out of 100
93
Key West Intl Airport
3.7 km•
See all flights
Car Hire
37 Restaurants
within 0.5 kilometers
Reviews
4.5
1,678 reviews
Reviews summary
This summary was created by AI, based on recent reviews.
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Southwinds Motel seems to have a mixed reputation among guests. While the service often receives commendations for the staff's welcoming nature, some guests report experiences of poor service. The motel's lively atmosphere, complete with nightly live music, adds to its quaint charm, although it might be too noisy for some.
Despite the praise for cleanliness and amenities like pools and an on-site bar, there are concerns about the value offered, with several travelers finding the rooms small and outdated. The location is generally well-regarded, offering proximity to attractions and the beach.
Location
Convenient
Atmosphere
Lively
Rooms
Dated
Value
Expensive
Cleanliness
Spotless
Service
Inconsistent
Amenities
Satisfactory
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Detailed Reviews
Hotel's Favourite
Staff were phenomenal!! Perfect location. Could walk to anywhere we wanted to go on Duval St. and the beaches. Our room was very clean and accommodating! We will definitely be going back really soon! Loved our 1st Key West adventure and will be staying at SouthWinds when we return!
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Date of stay: August 2023Trip type: Travelled as a couple
Value
Location
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from James Heineman, Owner at Southwinds Motel
Responded 25 Aug 2023
Dear 467selinak, Thank you so much for taking the time to write this Amazing Five Star review of our motel!! I was so pleased that your stay with us was so enjoyable and thanks for you 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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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
This is the third time we’ve stayed at this hotel they are very accommodating to our bicycle club and let us park our trailer. We stayed in rooms 38 and 39 which are the bigger suites by the smaller pool very nice area. There’s a king size bed and a queen size bed and a little kitchenette area. In a great location right near the southern most point and off of Duval Street. The beds and pillows were comfortable and The bathroom amenities were nice staff was very friendly and helped us out with booking the trolley tour- which a stop is right outside the hotels entrance
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Date of stay: January 2020Trip type: Travelled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 29 Jan 2020
Dear dluffman, 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 and we appreciate your feedback. We love our returning guests!!! 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. All the best, Jim Heineman VP Operations
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
A lot to digest? Read an AI-generated summary of recent traveller reviews.
I cannot say enough great things about our stay at The Southwinds Motel! Our room was very clean, with an extremely comfortable king bed. We were able to park close to our room each night. There are 3 very nice pools on the property, so ever room is just steps from a pool. Those are the basics that we look for in a vacation experience.
What we did not expect was the commitment of the staff to our enjoyment of our stay. They went far beyond the "welcome to our resort, here is a map of the grounds and a map of the town". One morning I went to the front desk to ask where I could rent a scooter near by. They contacted a vendor and arranged to have one delivered to the motel, within a half hour, for a cost of about half what I was expecting.
Winnfild, one of the staff was especially helpful. One evening, as we sat in front of the lobby at an umbrella table, drinking wine and talking, we decided to stay there and order a pizza. Winnfild gave us the number of the best pizza on the island and had it delivered.
When it came time to check out (this place is hard to leave), our plane didn't take off until late afternoon and we had a good deal of time to kill. Winnfild supplied us with beach passes, extended parking and a place to change clothes between the beach and airport. That was an amazingly generous act. We spend 10am til 2pm lying on the beach, soaking up the last rays of sun before returning to Western PA in February. My wife and I are already making plans to return.
I would strongly recommend this property to anyone who wants a clean, quiet, comfortable place that is close to everything and who's staff is really there for you.
What we did not expect was the commitment of the staff to our enjoyment of our stay. They went far beyond the "welcome to our resort, here is a map of the grounds and a map of the town". One morning I went to the front desk to ask where I could rent a scooter near by. They contacted a vendor and arranged to have one delivered to the motel, within a half hour, for a cost of about half what I was expecting.
Winnfild, one of the staff was especially helpful. One evening, as we sat in front of the lobby at an umbrella table, drinking wine and talking, we decided to stay there and order a pizza. Winnfild gave us the number of the best pizza on the island and had it delivered.
When it came time to check out (this place is hard to leave), our plane didn't take off until late afternoon and we had a good deal of time to kill. Winnfild supplied us with beach passes, extended parking and a place to change clothes between the beach and airport. That was an amazingly generous act. We spend 10am til 2pm lying on the beach, soaking up the last rays of sun before returning to Western PA in February. My wife and I are already making plans to return.
I would strongly recommend this property to anyone who wants a clean, quiet, comfortable place that is close to everything and who's staff is really there for you.
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Date of stay: February 2020
Location
Cleanliness
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 2 Mar 2020
Dear tstarmack, Thank you so much for taking the time to write this charming review of our motel. I was so pleased that your stay with us was so enjoyable and we appreciate your feedback. Winnfield, 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. All the best, Jim Heineman VP Operations
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
The king room (200 feet) is a bit tight, should have taken a queen room or sprang for queen with sofa for more space. Liked our room #48; wasn't facing directly to parking lot. Used the pool on the left of the office; very private and quiet. The heated pool was in a quieter area in the back, but we enjoyed the pool closer to our room. Staff cleaned rooms promptly. Breakfast (packaged muffins, bagels, yogurt, bananas and oranges, coffee and juice was plenty and very good. You take your food and drinks back to your room or to pool area with tables. Nice quiet area, away from Duval; the free Duval Loop bus is three short blocks away on Simonton & Catherine Street. This place had the best price with the amenities we needed (plenty of off street parking, continental breakfast, pools, microwave/coffee maker, fridge) and right next to Tipsy Rooster!
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Date of stay: March 2020Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 4 Mar 2020
Dear kathleen974, 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 and 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. All the best, Jim Heineman VP Operation
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Very good location at the corner of Simonton and South streets, just a block off of Duval and 2 blocks from the Southernmost Point buoy. We walked down to Mallory Square and Uber'ed home each night ($14).
The motel itself is relatively plain - nothing fancy and the room/bathroom is small but for the amount of time we were in it, it worked just fine. If we were staying longer than just the two nights, we probably would have looked for something different but this worked.
The continental breakfast is very basic but it was nice to have something convenient to get the day started. Even more convenient was having the Tipsy Rooster right next to the motel office to continue to get the day started and ended - a great location for people watching.
Two minor things that we noticed: the lounge chairs at the pool are a little old and "tired" - not a lot of life left in them, and it would have been nice to have a chair or two outside the room as the room is fairly small and the weather was nice each morning before we started the day and when returned at night. I'd still recommend the motel but just something to consider.
The motel itself is relatively plain - nothing fancy and the room/bathroom is small but for the amount of time we were in it, it worked just fine. If we were staying longer than just the two nights, we probably would have looked for something different but this worked.
The continental breakfast is very basic but it was nice to have something convenient to get the day started. Even more convenient was having the Tipsy Rooster right next to the motel office to continue to get the day started and ended - a great location for people watching.
Two minor things that we noticed: the lounge chairs at the pool are a little old and "tired" - not a lot of life left in them, and it would have been nice to have a chair or two outside the room as the room is fairly small and the weather was nice each morning before we started the day and when returned at night. I'd still recommend the motel but just something to consider.
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Date of stay: February 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 4 Mar 2020
Dear WoodSoxCT, Thank you so much for taking the time to write this nice review of our motel. I was so pleased that your stay with us was so enjoyable and 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. All the best, Jim Heineman VP Operation
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
We took my in-laws to Southwinds for Christmas and were very disappointed. The floors of our room were destroyed by a previous flood, the deadbolt on the door didn't work, the toilet wasn't bolted down, the Internet never worked. The rooms were VERY small and VERY, VERY noisy. We could hear entire conversations from the room next to us. We were charged an additional "convenience" fee for parking and breakfast. We didn't drive, therefore didn't need the parking and the breakfast was hardly enough to actually feed someone. It mostly consisted of old muffins. When we pointed this out to the employee, he was very flippant about it. We were also charged a $100 deposit, separate of other charges. Most hotels just hold the card on record, but they made a point to say they would be charging the card $100 and refund it later. They were also very arrogant about that charge as well.
The only positive about Southwinds was the location, but definitely not worth the price or the hassle.
The only positive about Southwinds was the location, but definitely not worth the price or the hassle.
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Date of stay: December 2019
Value
Rooms
Service
Room Tip: Don't choose this hotel. The rooms are all very small and very noisy.
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 3 Jan 2020
Dear AngelaD672, Thank you for taking the time to give me your direct feedback on your recent stay with us at our motel in Key West. I am sorry that we could not meet you expectations and that our fees for our services were not clearly explained to you at the time of your reservation. I have shared your comments with the team at the motel and we will use the feedback to better educate and train our staff members on customer service. All the best, Jim Heineman VP Operations
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from James Heineman, Owner at Southwinds Motel
Responded 22 Nov 2020
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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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
We made a last minute reservation for two rooms for an overnight in the keys. Shara was on duty when we arrived. Shara was very friendly and courteous. Right away we felt welcomed. Her demeanor was genuine and caring. What a wonderful person you have on your team! The rooms were spacious and clean. They are not modern but if you like that vintage Florida look in a clean room with everything you need (iron & board, coffee maker, refrigerator, and microwave in the room), then you will like this place. We slept peacefully in comfortable beds. In the morning, Karen was on duty in the office. Karen was friendly and courteous and helpful with the breakfast items. The included breakfast was juice, coffee, and muffins. There are so many great restaurants within walking distance so we didn’t need more than this as we had breakfast elsewhere. I hope the owners and managers know how fortunate they are to have two such amazing employees working with them!
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Date of stay: February 2021
Rooms
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Jim Heineman, Owner at Southwinds Motel
Responded 6 Feb 2021
Dear RafeJ, Thank you so much for taking the time to write this Five Star review of our motel. I was so pleased that your stay with us was so enjoyable. We appreciate your feedback. Shara and Karen are just two 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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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
We stayed 4 nights. The hotel is in a good location & is walking distance to duvall street & a beach.
There are 3 pools on the grounds but we just used the one near our room. It needs to be resurfaced. A lot of the pool’s bottom seemed gouged & had some stains. We still had a good time though.
Our room was very small but clean. There was a mini fridge & microwave on a small counter area.
There is no closet or dresser. There was a small hanging rack attached to the wall.
The bathroom was the worst part. It was minuscule. The sink was half the size of most & was pedestal style- no bathroom counter. The only place to put toiletries you don’t want in the shower is the window ledge. & whenever i washed my face i got water everywhere. The shower was a decent size but our first day we had terrible water pressure. Luckily staff responded quickly to our concern & replaced the shower head- which fixed the problem.
There is a $20 a day resort fee, which covers breakfast, parking, & the pools. We were told due to covid the normal breakfast was reduced to coffee/juice/water & muffins. So a muffin is the ONLY food item at breakfast. Yet they still charge the same $20 they did before reducing the breakfast. Since i have celiac disease i got zero of the complimentary breakfast food i was charged for.
There is a cool walk up bar/liquor store on the edge of the property- the tipsy rooster. There is also a convenience store with a sandwich counter across the street.
There are 3 pools on the grounds but we just used the one near our room. It needs to be resurfaced. A lot of the pool’s bottom seemed gouged & had some stains. We still had a good time though.
Our room was very small but clean. There was a mini fridge & microwave on a small counter area.
There is no closet or dresser. There was a small hanging rack attached to the wall.
The bathroom was the worst part. It was minuscule. The sink was half the size of most & was pedestal style- no bathroom counter. The only place to put toiletries you don’t want in the shower is the window ledge. & whenever i washed my face i got water everywhere. The shower was a decent size but our first day we had terrible water pressure. Luckily staff responded quickly to our concern & replaced the shower head- which fixed the problem.
There is a $20 a day resort fee, which covers breakfast, parking, & the pools. We were told due to covid the normal breakfast was reduced to coffee/juice/water & muffins. So a muffin is the ONLY food item at breakfast. Yet they still charge the same $20 they did before reducing the breakfast. Since i have celiac disease i got zero of the complimentary breakfast food i was charged for.
There is a cool walk up bar/liquor store on the edge of the property- the tipsy rooster. There is also a convenience store with a sandwich counter across the street.
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Date of stay: July 2020Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Jim Heineman, General Manager at Southwinds Motel
Responded 14 Jul 2020
Dear livi422, 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 and 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. All the best, Jim Heineman VP Operation
Read more
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
The Southwinds was a quiet, reasonable, friendly place to stay for us. We were in Key West for a wedding, and wanted to stay somewhere that wasn’t in the heart of Duvall & all the action - but a place where we could get to the action when we wanted to. It’s true that it’s a bit funky, and on first glance, it might seem like you’re paying an awful lot for what’s basically a motel. But for Key West prices and location, it’s very reasonable.
We found the staff to be incredibly friendly and helpful. We got there early after a red-eye flight, and couldn’t check in right away, but were offered a place to change clothes, stash bags, and hit the beach (complete with coupon for beach chairs & towels). Thought that was a nice touch.
We had the basic room, which, it must be said, is somewhat small (and the bathroom is tiny). We didn’t need anything fancier, though, and it was very clean, and everything worked. So, no problem for us.
You’re right across the street from Ana’s Cuban cafe & grocery, which is a great place for breakfast, lunch, and/or Cuban coffee. Very near South Beach (see above) and also just a couple of blocks from the Southernmost Point buoy. The free Duvall Loop shuttle goes right past the motel, so it’s easy to get around KW that way.
All in all, if you’re looking for a straightforward place to stay that’s clean, quiet, and friendly, stay at the Southwinds.
We found the staff to be incredibly friendly and helpful. We got there early after a red-eye flight, and couldn’t check in right away, but were offered a place to change clothes, stash bags, and hit the beach (complete with coupon for beach chairs & towels). Thought that was a nice touch.
We had the basic room, which, it must be said, is somewhat small (and the bathroom is tiny). We didn’t need anything fancier, though, and it was very clean, and everything worked. So, no problem for us.
You’re right across the street from Ana’s Cuban cafe & grocery, which is a great place for breakfast, lunch, and/or Cuban coffee. Very near South Beach (see above) and also just a couple of blocks from the Southernmost Point buoy. The free Duvall Loop shuttle goes right past the motel, so it’s easy to get around KW that way.
All in all, if you’re looking for a straightforward place to stay that’s clean, quiet, and friendly, stay at the Southwinds.
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Date of stay: March 2020Trip type: Travelled with friends
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from MHMSKW, Owner at Southwinds Motel
Responded 9 Mar 2020
Dear KDUB7, 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 and 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. All the best, Jim Heineman VP Operation
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
None of our King Rooms face a pool.
Jim Heineman VP Operations
You can smoke outside at Tipsy Rooster.
Jim Heineman VP Operations
There are two main options. The first is to grab a taxi which are located right out side the baggage claim area. The other is to use an Uber if you have that app on your phone.
All the best, Jim Heineman VP Operations
Yes, you are able to smoke in any of the outside areas, but not in the guest rooms or the lobby.
All the best,
Jim Heineman VP Operations
Typically our rooms with two beds are larger that our rooms with a king bed.
All the best, Jim Heineman VP Operations
…
"Live music at adjacent bar goes until midnight, so earplugs would be helpful if you are early to bed. An over door organizer also helpful."Read full review
"The pool was great! The people were so nice at this hotel and you get a free continental breakfast. It was perfect! Nice and private!"Read full review
"Ask for a room on the inside of the square, or in the back part next to the small pool"Read full review
"What's nice is having a parking spot, considering parking is a premium in Key West.."Read full review
…
PRICE RANGE
HK$1,318 - HK$2,597 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
southwind hotel key west
LOCATION
United StatesFloridaFlorida KeysKey West
NUMBER OF ROOMS
58
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.
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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 (0.2 km), Alan S. Maltz Gallery (0.3 km), and Tipsy Rooster Liquor Store & Bar (0.02 km).
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, The Lobster Shack Key West, and La Grignote.
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 centre?
Yes, it is 0.8 km away from the centre 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, and Latvian.
Are there any historical sites close to Southwinds Motel?
Many travellers enjoy visiting Key West Garden Club (0.9 km), Truman Little White House (1.5 km), and West Martello Tower (0.8 km).