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Southwinds Motel

2.0 star property

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning
$180
includes taxes & fees
Oct 14 - Oct 15

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.)
    ‪7 min drive‬

Room options

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Property grounds

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  • Breakfast included
  • Pet friendly
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4.4 out of 5, Excellent, 1,010 reviews
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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.

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

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 694 out of 1195 reviews
Rating 8 - Good. 307 out of 1195 reviews
Rating 6 - Okay. 126 out of 1195 reviews
Rating 4 - Poor. 50 out of 1195 reviews
Rating 2 - Terrible. 18 out of 1195 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

10/10 Excellent

Lola

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was great. It was convenient in the middle of everything. It had two pools. It was an older place, but had charm.
Stayed 5 nights in Jun 2025

10/10 Excellent

Tamara, Lantana

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Tamisha was amazing, her smile light up the room when my family and i walked in. She was very patient and helped us . I was very ease. Thank you.
Stayed 2 nights in Jul 2025

10/10 Excellent

Rosmery

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Th staff is amazing and really friendly. The place is just what you need to be close to everywhere and easygoing people. Love it should be rate with higher stars
Stayed 1 night in Jul 2025

8/10 Good

Ruth

Stayed 2 nights in Jun 2025

10/10 Excellent

Linda

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Older property, but clean and very well kept. The staff were very friendly and helpful.
Stayed 2 nights in Jul 2025

6/10 Okay

Jeremy

Traveled with partner
Liked: Cleanliness, staff & service, amenities
I would inquire about the bathroom size before booking or you might have issues. Otherwise, the location and amenities were nice including a bar with live entertainment and an ice cream truck.
Stayed 3 nights in Jun 2025

10/10 Excellent

cynthia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
We stay here when ever we’re in the keys
Stayed 6 nights in Jul 2025

10/10 Excellent

Shaun

Alway stay at southwinds!!! Absolutely perfect!!
Stayed 3 nights in Jul 2025

6/10 Okay

John, La Cygne

Traveled with group
Liked: Cleanliness, property conditions & facilities
Staff was not helpful. Our friends from France booked for 4 and were given a room that did not accommodate them. My wife and I swapped rooms as we had two beds and only needed one. Staff said error was made by booking by third party and not directly.
Stayed 2 nights in Jul 2025

8/10 Good

Thomas

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jun 2025

8/10 Good

Pamela

Traveled with group, Traveled with family
Liked: Cleanliness
property was good for the cost
Stayed 2 nights in Jul 2025

6/10 Okay

Gregory

Stayed 4 nights in Jul 2025

10/10 Excellent

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities
Stayed 4 nights in Jul 2025

8/10 Good

John

Traveled with group
Liked: Cleanliness, staff & service, room comfort
Stayed 7 nights in Jun 2025

10/10 Excellent

Elizabeth

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always stay at Southwinds. Like the location
Stayed 2 nights in Jun 2025

8/10 Good

Crystal

Liked: Cleanliness, amenities, property conditions & facilities
It is everything you need. Clean rooms, hot showers, two pools, ice and washer and dryer. Small breakfast and on the quiet end of the adventures. Grocery store across the street, ice cream and bar/restaurant on site. Excellent pricing and friendly staff. Thank you for an incredible girls trip. We will see you soon.
Stayed 4 nights in Jun 2025

10/10 Excellent

James

Traveled with family
Liked: Cleanliness, amenities
Great location. Good value, small rooms because they have updated a motel from a past era. Friendly helpful staff. Laundry room was a plus.
Stayed 2 nights in Jun 2025

6/10 Okay

Janet

Liked: Cleanliness, staff & service, property conditions & facilities
Bathroom too small
Stayed 3 nights in Jun 2025

10/10 Excellent

Stacey

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Jun 2025

10/10 Excellent

Susan

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property is amazing. Two pools, one heated. Free laundry (with detergent!). Front desk did magic and got me my room for a second night. Coupon for free umbrella and towels at the beach around the corner. Go get a Classic Cuban from Ana’s Cafe right across the street. Right on the Duval Loop Trolley. Great value for money. Highly Recommend!
Stayed 1 night in Jun 2025

10/10 Excellent

Amy

Stayed 4 nights in Jun 2025

10/10 Excellent

Cyrenah

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Was very clean, air conditioner worked very well, pool was good, but closed pretty early. Great value considering its one of the cheaper places in Kwy West. Will definitely be staying there for our next trip.
Stayed 4 nights in Jun 2025

10/10 Excellent

Steven

Liked: Cleanliness, amenities, property conditions & facilities
My room was very clean and the bed was extremely comfortable. The bathroom was a little small for me but im a 6'4" big guy. Great bar right on the property. Close proximity to just about anywhere a tourist would want to go. Very nice pool. Every guest was very friendly. Staff is extremely helpful and friendly. I loved my stay. I recommend to anyone who wants to visit key west.
Stayed 5 nights in Jun 2025

10/10 Excellent

Linda

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The location was perfect! Everything is right there, it's safe and the staff was wonderful!
Stayed 1 night in Jun 2025

10/10 Excellent

Andreanna

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean, great location, and stay.One of the most affordable options in Key West.
Stayed 3 nights in Jun 2025