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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
Property grounds
Standard Room, 2 Queen Beds
Reception
Front of property

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air-conditioning
  • Bar

Explore the area

View in a map
1321 Simonton Street, Key West, FL, 33040
  • Place, Duval Street
    ‪3 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down duvets, pillow-top beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(107 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(80 reviews)
  • 37 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down duvets, pillow-top beds, individually decorated

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Standard Room, 1 King Bed

8.4 out of 10
Very good
(114 reviews)
  • 28 sq m
  • Sleeps 3
  • 1 King Bed

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About this property

Southwinds Motel

2 outdoor pools, a bar/lounge, and self parking are available at this hotel. Continental breakfast is free. Other amenities include coffee/tea in a common area, concierge services, and laundry facilities. 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.

Our customers tell us they enjoy the free breakfast at Southwinds Motel. During your stay, you're just a quick walk from Florida Keys Beaches. Enjoy features like 2 outdoor pools, a bar, and concierge services.
  • Free continental breakfast served daily
  • Enjoy drinks at the bar/lounge
  • Self parking available for a fee
  • Take a swim in the 2 outdoor pools
  • Services include a concierge, tour or ticket assistance, and luggage storage
  • Guests really like the accommodations for the comfy beds and cleanliness
  • Steps from South Beach and 3 minutes by foot from Duval Street
Southwinds Motel offers its guests 2 outdoor swimming pools. You can enjoy a drink at the bar/lounge. Free breakfast is available daily.

A vending machine, multilingual staff, and tour/ticket assistance are also featured at Southwinds Motel. For a fee, parking is available.

Smoking is allowed in designated areas at this Key West hotel.

Guests are served free continental breakfast daily from 7:00 AM to 10:00 AM.
Tipsy Rooster - This bar serves light fare only.

Property amenities

Parking and transport

  • Parking on site (USD 22.50 per day)
  • Limited on-site self parking

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

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room cot
  • 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

  • No lift

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free cot
  • 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
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Free cribs (infant beds)!

Payment types at the property

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • Resort fee: USD 33.75 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access

We've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Self parking fee: USD 22.50 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
Front desk staff will greet guests on arrival at the property.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.
  • Alcohol isn't served at Southwinds Motel.

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

8.6

Excellent

Rating 10 - Excellent. 731 out of 1321 reviews
Rating 8 - Good. 355 out of 1321 reviews
Rating 6 - Okay. 148 out of 1321 reviews
Rating 4 - Poor. 59 out of 1321 reviews
Rating 2 - Terrible. 28 out of 1321 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

8/10 Good

Bryan

Travelled with partner, Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Nothing bad to say at all. I get its Key West but for the money i felt it could have been a little nicer. Staff was friendly and everything did in fact work. I would stay there again.
Stayed 1 night in Jan 2026

6/10 Okay

Connie

Liked: Cleanliness
Room clean. Lacked shower pressure with luke warm water. Room service every 3 days for a higher price motel room. Had to go to front desk daily for two fresh towels daily. We stayed 6. The staff and maintained was always pleasant.
Stayed 6 nights in Jan 2026

8/10 Good

Khristie

Liked: Cleanliness, amenities
Clean spacious room with good amenities. Staff was adequate. Housekeeping only every 3 days and they didn't bother to show them.
Stayed 6 nights in Jan 2026

4/10 Poor

Anna, State College

Travelled with group
Disliked: Amenities, property conditions & facilities
Pictures did not reflect the condition of the motel. It was in need of an overhaul and our room had the bare minimums - very limited. . . had to unplug the coffee maker to plug in the microwave. Wouldn't stay there again.
Stayed 5 nights in Jan 2026

8/10 Good

Louis

Travelled with family
Liked: Cleanliness
Location
Stayed 3 nights in Jan 2026

10/10 Excellent

Brandy Lynn

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Super cute! Perfect location. We would stay again.
Stayed 3 nights in Jan 2026

10/10 Excellent

Sherri

Liked: Cleanliness, staff & service, amenities
Wonderful room by the pool. Excellent staff, great location to be able to walk just about anywhere on the island.
Stayed 1 night in Jan 2026

8/10 Good

Sherri

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Southwinds is an older motel in the heart of Key West. Easy to walk just about anywhere from their location. Room was clean, great bed and wonderful staff. Only problem was that we were close to the bar, so lots of loud music at night. We didn’t complain or ask to be moved as we were there during the KW Marathon, and all the rooms were full. We did add an extra day to our stay, and they placed us in a great room by the heated pool. Would definitely stay there again, just not close to the bar.
Stayed 3 nights in Jan 2026

6/10 Okay

Nancy

Travelled with group
It was a shabby mitel
Stayed 1 night in Jan 2026

10/10 Excellent

JOHN, milford

Stayed 1 night in Jan 2026

6/10 Okay

Jeffrey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Clean room, but no black out drapes or shades. The lights on the building shine in the room. Staff was great and Tipsy Rooster is a great place to hang out.
Stayed 5 nights in Jan 2026

10/10 Excellent

Aaron

Stayed 1 night in Jan 2026

6/10 Okay

Robert

Travelled with partner
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
Room was ok, small but clean. Location was good, easy access to the beach, Duval, about a 35 min walk to the west side and port. Used to be free parking but now are charging. Not sure what the resort fee paid for outside of the pool. Downside. Staff was not friendly or helpful. Acted as if we were inconveniencing them the entire week we were there. Complimentary breakfast was pretty weak. No hot water on our last day/night. Pretty loud each evening with the band in the bar anywhere from 6pm to past 10 depending on the evening - felt like they were in our room on a couple of nights. First trip to Key West and our stay here was disappointing. Would not come back to this facility.
Stayed 7 nights in Jan 2026

10/10 Excellent

Lucy

Travelled with partner
Liked: Amenities
Everyone was nice and courteous. Quiet place. Really enjoyed our weekend
Stayed 3 nights in Jan 2026

8/10 Good

Susie

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very clean. Great location. Small rooms. WiFi did not work very well in our room (#5). But we would stay here again.
Stayed 3 nights in Jan 2026

8/10 Good

Frederick

Travelled with partner
Liked: Cleanliness, staff & service, amenities
Very low water pressure. Showing it's age
Stayed 2 nights in Jan 2026

4/10 Poor

Robin

Stayed 1 night in Jan 2026

8/10 Good

Tom

Travelled with family, Travelled with pets
Liked: Cleanliness, property conditions & facilities
The room was nice, clean and comfortable. It was a bit small as we travel with our little dogs, however it had a great bed. The faucet and shower controls should be replaced as it was very difficult to adjust the temperature on both. The staff was great and the breakfast was the best. Value was worth the price.
Stayed 3 nights in Jan 2026

10/10 Excellent

James

Liked: Amenities
Old Needs updating Great location Friendly staff
Stayed 4 nights in Jan 2026

6/10 Okay

steve

Stayed 2 nights in Jan 2026

8/10 Good

john

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location was great, close to 2 beaches. Property was nice and clean. Rooms were small but fine. Was there 4 days and basically had bad oranges and no other fruit for the time spent. Had plenty of bagged muffins, yogurt, and cereals. One beaches supplier you with towels and chair you just have to get a pass from the front desk. Great outside live music every night. Would definitely stay again.
Stayed 4 nights in Jan 2026

6/10 Okay

Tatiana

Travelled with family
Liked: Cleanliness, amenities
Disliked: Property conditions & facilities
Guys for the price this is pretty run down property even though the rooms were clean. The breakfast served was really a junk. I understand that I decided to stay in a MOTEL but still, even cheap food can be better quality. The staff was courteous and professional and friendly. Really, just staff and room cleanliness were positives of this place.
Stayed 4 nights in Jan 2026

10/10 Excellent

MATTHEW

Liked: Cleanliness, staff & service, amenities
Staff was wonderful, pleasantly surprised that we got free towels and chairs at beach.
Stayed 7 nights in Dec 2025

10/10 Excellent

Heather

Travelled with family
Liked: Cleanliness, staff & service, amenities
Everyone enjoyed it. The warm pool was very nice. The location was wonderful.
Stayed 3 nights in Jan 2026

6/10 Okay

Michael

Liked: Staff & service
Stayed 2 nights in Jan 2026

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