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Southwinds Motel

2.0 star property

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Exterior
Deluxe Room | Living area | 32-inch LED TV with cable channels, TV
Deluxe Room | Terrace/patio
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
2 outdoor pools, pool umbrellas, sun loungers

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning

Explore the area

Map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Southernmost Point
    ‪4 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 King Bed

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 2 Queen Beds

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

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  • Breakfast included
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The price is $336
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$398 total
includes taxes & fees
Mar 26 - Mar 27
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About this property

Southwinds Motel

Hotel in Old Town Key West
2 outdoor pools, a bar/lounge, and coffee/tea in a common area are available at this hotel. Continental breakfast is free. Additionally, concierge services, laundry facilities, and a 24-hour front desk are onsite. Housekeeping is available on request.
Southwinds Motel offers 58 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Pillowtop beds feature down comforters and premium bedding. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include showers and complimentary toiletries.

32-inch LED televisions come with cable channels. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is provided on request.

2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Southwinds Motel features 2 outdoor swimming pools. A bar/lounge is on site where guests can unwind with a drink. Guests can enjoy a complimentary breakfast each morning.

This Key West hotel also offers a vending machine, multilingual staff, and tour/ticket assistance.

Southwinds Motel has designated areas for smoking.

A complimentary continental breakfast is served each morning between 7:00 AM and 10:00 AM.
Tipsy Rooster - This bar serves light fare only.

Languages

English, Russian, Spanish

Property amenities

Parking and transportation

  • Limited onsite parking
  • Wheelchair-accessible parking available

Food and drink

  • Free continental breakfast available daily 7:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tipsy Rooster

Things to do

  • 2 outdoor pools
  • Bicycle rentals

Family friendly

  • 2 outdoor pools
  • Highchair
  • In-room crib
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Laundry facilities
  • Luggage storage
  • Vending machine

Guest services

  • Concierge services
  • Housekeeping (on request)
  • Multilingual staff
  • Proposal/romance packages
  • Tour and ticket assistance

Outdoors

  • Beach loungers
  • Beach towels
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Pool loungers
  • Pool umbrellas

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Wheelchair-accessible parking

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free crib
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Entertainment

  • 32-inch LED TV with cable channels

Food and drink

  • Cleaning supplies
  • Coffee/tea maker
  • Microwave
  • Paper towels
  • Refrigerator

More

  • Access via exterior corridors
  • Air conditioning
  • Electrical adapters
  • Free local calls
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Phone
  • Window screens

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: midnight
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children are welcome
Children up to the age of 13 years can stay for free if using existing beds when occupying the parent or guardian's room
Rollaway/extra beds are not available
Free cribs are available on request at the property

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 28.13 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access
  • Self parking

We have included all charges provided to us by the property.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Minimum Spring Break check-in age is 18 years old
The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
This property accepts credit cards, debit cards, and cash
Safety features at this property include a carbon monoxide detector and a smoke detector

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms
Alcohol is not served at this property

Property is also known as

Southwinds Motel Key West
Southwinds Motel
Southwinds Key West
Southwind Hotel Key West
Southwinds Motel Hotel
Southwinds Motel Key West
Southwinds Motel Hotel Key West

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 617 out of 1082 reviews
Rating 8 - Good. 285 out of 1082 reviews
Rating 6 - Okay. 116 out of 1082 reviews
Rating 4 - Poor. 43 out of 1082 reviews
Rating 2 - Terrible. 21 out of 1082 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

6/10 Okay

Christina M

Traveled with family
Liked: Staff & service
Unfortunately our room was directly Next to the rooster bar and we heard the people In there and the music well into 3am every night - made for very poor sleeping conditions. Also when showering the hot and cold handles did not work, made for very cold Showers which was really too bad, wouldn’t recommend or stay here again
Stayed 2 nights in Dec 2024

8/10 Good

Kelly

Traveled with group
The music at night
Stayed 3 nights in Dec 2024

10/10 Excellent

Deborah, Woburn

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is our second stay at southwinds. Great place to stay.
Stayed 1 night in Dec 2024

4/10 Poor

Patrick, Richmond Hill

Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
The exterior door of the room was a hollow wood door. Hollow wood doors are intended for interior use such as closets, bathrooms, etc., not exterior. For proper security, an exterior door should be either metal or solid wood. Even though the door on the room I stayed in had two locks, including a dead bolt, a hollow wood door can be broken open in minutes, if not seconds, with ordinary common hand tools or it can be kicked apart. This is a serious security lapse. Additionally, there was a gap between the bottom of the door panel and the threshold that likely permitted a large cockroach that I found in the room on my third night there to gain access to the room. Someone at the front desk told me that the roaches live in the trees outside so it probably got in under the door. It would seem that if they knew about the roaches, measures should have been taken (such as better fitting doors with barriers along the bottoms) to keep them out of the rooms. Other possible intruders, such as mice, could probably squeeze through too. Other issues that I noticed didn't seem well thought out such as the location of the wall mounted TV; most of the screen could not be seen from the bed if the outward swinging bathroom door was open by more than about a foot. It could have been mounted elsewhere. Overall, the room was clean, the bed was comfortable and the air conditioner worked well. Everything worked well in the bathroom though the sink faucet was a bit loose and moved slightly.
Stayed 4 nights in Dec 2024

8/10 Good

Molly

Traveled with group
Great place
Cute place. Quiet. Great location. 2 pools.
Stayed 3 nights in Dec 2024

8/10 Good

Eric

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice older property, walking distance to Duval street. Great bar next to the property with live music.
Stayed 2 nights in Dec 2024

8/10 Good

Cynthia, Hamilton

Traveled with family
Air conditioner comes on and shuts off every 2 minutes. Very loud water pressure was great for cold water. Hot water trickled
Stayed 2 nights in Dec 2024

10/10 Excellent

Norbert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quint little cottages
Stayed 1 night in Dec 2024

6/10 Okay

zues

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Had bugs only 2 but don't think they were a lot a few maybe roaches not sure
Stayed 3 nights in Dec 2024

10/10 Excellent

Robert

Stayed 1 night in Nov 2024

8/10 Good

Tim

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Not fancy but good
This hotel is in such a great location. You can walk to everything in the historic part of town or rent a bike and go everywhere! It was a small room but clean and very comfortable bed. There is a beach nearby and also a nice pool. Breakfast was better than I expected and the coffee was really good. We have been here before and will probably be back.
Stayed 2 nights in Dec 2024

8/10 Good

Jacqueline

Liked: Cleanliness, staff & service, property conditions & facilities
Nice old school motel
Stayed 2 nights in Nov 2024

10/10 Excellent

Dan

Traveled with partner
The staff here are wonderful. They go above and beyond to accommodate. We were especially impressed with Winfield.
Stayed 2 nights in Dec 2024

8/10 Good

ron

Traveled with partner
Liked: Cleanliness, staff & service
Room was ok but some outlets could only be used with ceiling lights left on. Bed had large hump in the middle.
Stayed 2 nights in Dec 2024

10/10 Excellent

Jolanta

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Nov 2024

8/10 Good

IVON

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
safe
Stayed 2 nights in Nov 2024

10/10 Excellent

SATISH

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
What a hidden gem and so close to Duval Street!! Stay here and do the Southen Most Point in the morning at sunrise. And thank me later 😍
Stayed 1 night in Nov 2024

10/10 Excellent

Kevin Robert

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a reasonably priced Motel with a bar and liqoir store attached, also had a small grocery store across the street.
Stayed 7 nights in Nov 2024

8/10 Good

Nadia

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved how convenient it is to all amenities.
Stayed 4 nights in Nov 2024

8/10 Good

Michele

Traveled with group
Disliked: Property conditions & facilities
Quaint but needs repairs
The motel grounds are very well kept and are quiet and clean. The front office is cute and clean. The room we were given in the back of the lot was large but was in need of some simple repairs. For the cost of the room the quality of the room was not inline. Good location and easy access. They just need to make simple repairs that make a big difference. Our phone did not work, the tv did not work but they did come mess with it and it finally worked. We plugged in a hairdryer and it blew a breaker - they did come fix that as well. The service was good, the room was so so.
Stayed 2 nights in Nov 2024

10/10 Excellent

Dennis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Iris at the front desk was Fantastic! She checked us in on a phone call as we arrived after hours. Was a pleasure ...
Stayed 3 nights in Nov 2024

4/10 Poor

Trevor

Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
Beware that there is a bar at the property with live music in the evening that goes til 1:30 a.m. This bar was right beside my window. I was told at checkin that the music only went til 11 p.m., which I didn't think was unreasonable. However when it was still going strong at 12:30, I called reception and was told, "No, it doesn't end til 1:30 a.m." I find it hard to believe that they didn't know that when I checked in. At first the manager was not willing to allow me to cancel my second night and get a refund. It was only after I got Expedia involved (thanks to the helpful folks at Expedia) that he was willing to do so. He remainded unwilling to discount my first night. So I paid $350 CAD for 3 1/2 hours sleep. He assured me that he would let all staff know how late the music actually goes, so if you are told otherwise, let my lesson be your guide. Otherwise the property is fine and the bed was comfortable. It will work if you don't mind live music literally outside your room (Room 19) til 1:30 a.m.
Stayed 2 nights in Nov 2024

6/10 Okay

Steve

Traveled with group
Stayed 3 nights in Nov 2024

10/10 Excellent

Michelle

Liked: Cleanliness, staff & service, property conditions & facilities
Great location. Friendly helpful staff. Room clean.
Stayed 3 nights in Nov 2024

8/10 Good

Theresa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Nov 2024