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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Exterior
Reception
2 outdoor pools, pool umbrellas, sun loungers
Property grounds
Exterior

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning
$169
includes taxes & fees
Sep 18 - Sep 19

Explore the area

View in a map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Southernmost Point
    ‪5 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪7 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

8.4 out of 10
Very good
(101 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)
  • 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

8.8 out of 10
Excellent
(65 reviews)
  • 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

8.4 out of 10
Very good
(88 reviews)
  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

Similar properties

Property grounds

The Palms Hotel

  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
4.3 out of 5, Excellent, 1,004 reviews
The Palms Hotel

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.

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
  • High chair
  • 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
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

Reviews

Southwinds Motel Reviews

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness
Rating 10 - Excellent. 683 out of 1178 reviews
Rating 8 - Good. 303 out of 1178 reviews
Rating 6 - Okay. 125 out of 1178 reviews
Rating 4 - Poor. 49 out of 1178 reviews
Rating 2 - Terrible. 18 out of 1178 reviews

Reviews

8/10 Good

Denise

Disliked: Property conditions & facilities
A little rundown and could be cleaner but area was awesome and very convenient.
Stayed 2 nights in Jun 2025

10/10 Excellent

Thalia

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property has so much parking and even let us park our golf carts that we rented. The staff is so nice.
Stayed 1 night in Jun 2025

8/10 Good

Maximo

Traveled with family
Liked: Cleanliness, property conditions & facilities
Great location close to everything around old town key west
Stayed 4 nights in Jun 2025

8/10 Good

Dawn

Stayed 1 night in Jun 2025

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It is not fancy, but the price was right. A block from Duval. Rent a bike and you will rule! Pool was cleanand well maintained. Pretty 420 friendly. At least no one bothered me about smoking on the property.
Stayed 7 nights in Jun 2025

10/10 Excellent

Heidi

Liked: Cleanliness, staff & service, property conditions & facilities
Thanks for a great stay.
Stayed 1 night in Jun 2025

6/10 Okay

Melissa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in May 2025

10/10 Excellent

Eric

Stayed 1 night in Jun 2025

10/10 Excellent

Kent

Stayed 6 nights in May 2025

10/10 Excellent

Jonathan

Stayed 3 nights in May 2025

8/10 Good

Robert, Lake Worth

Traveled with group
Liked: Amenities
Its rundown but location is great, bar and liquor store attached to it made it fun. This isnt for luxury travel, its a place to sleep and shower but thats all you need in key west
Stayed 3 nights in May 2025

10/10 Excellent

Jonnie

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
On site bar ice cream close to everything.
Stayed 2 nights in May 2025

10/10 Excellent

Gayle

Traveled with group
Liked: Cleanliness, property conditions & facilities
Check in was great! Very friendly. Need to clean floors in the room and repair show valve.
Stayed 2 nights in May 2025

10/10 Excellent

Eiko

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Southwinds Motel is very charming and room was very clean. Front desk staff were very friendly and helpful. My most favorite part is that there is a Tipsy Rooster bar and liquor store located right front of this motel. They have a live entertainment everyday, bar staffs were super friendly and drinks were delicious. Even though there are live entertainment everyday, the place was very quiet during the night. It is conveniently located to many restaurants, gift shops, and tram stop. Walking distance to the beach and other interesting visitor spots. When I visit Key again, I will definitly stay there again.
Stayed 2 nights in May 2025

8/10 Good

Mayelin

Good place to stay
Stayed 1 night in May 2025

6/10 Okay

James, Aurora

Liked: Cleanliness
Room was just very basic and small. About the only thing the room was good for was for sleeping. We were only there for one night so not a big deal, but if staying longer it would have been a problem to spend any real time in the room except to just go to sleep for the night. Front desk check-in was not great as the young man checking us in was not very friendly.
Stayed 1 night in May 2025

10/10 Excellent

Michelle, Gaylord

Stayed 1 night in May 2025

8/10 Good

Julie

Traveled with family
Pro- Older motel in great location for walking to beach, restaurants and nearby attractions. Front desk staff friendly and hotel offers chairs and towels for the beach. Heated outdoor pool was small, but fabulous. Room clean, but floor tile grout needed some extra attention. Con- Inadequate lighting in room unless overhead light on. Unable to adjust air conditioning unit. TV without signal(reported, but no one came to fix). No seating except bed or counter stools( sm easy chairs would be nice).
Stayed 5 nights in May 2025

10/10 Excellent

andres

Liked: Cleanliness, staff & service, property conditions & facilities
Cerca de la bolla de las 90 millas y con muchos
Stayed 1 night in May 2025

6/10 Okay

amber

Stayed 5 nights in May 2025

10/10 Excellent

Paul

Liked: Cleanliness, amenities, property conditions & facilities
Nice place. Clean. Nice pools. Close to amenities
Stayed 1 night in May 2025

6/10 Okay

Edward

Stayed 4 nights in May 2025

8/10 Good

Leonard Cour

Stayed 4 nights in May 2025

8/10 Good

John

Stayed 2 nights in May 2025

8/10 Good

CARRIE

Traveled with partner
Liked: Cleanliness, amenities
The hotel was great for our stay, walkable to Duvall, a little far to the hot spots on Duval, which was fine for us. Scooter rental was totally worth it. Didn’t use the pools, the bar was cool, nice area. Free parking. The bathroom was tiny and there was no where to put shower toiletries, but it worked for two people. Would stay there again!!
Stayed 4 nights in May 2025