Southwinds Motel

2.0 star property
Hotel with 2 outdoor pools, near Duval Street

Choose dates to view prices

Southwinds Motel

Photo gallery for Southwinds Motel

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Shower, free toiletries, hair dryer, towels

Overview of Southwinds Motel



Property highlights

  • Pool
  • Parking available
  • Bar
  • Laundry facilities
  • Air conditioning
  • 24/7 front desk
1321 Simonton Street, Key West, FL, 33040
Main amenities
  • Daily housekeeping
  • Near the beach
  • 2 outdoor pools
  • Beach sun loungers
  • Beach towels
  • Bar/lounge
  • 24-hour front desk
  • Coffee/tea in a common area
  • Air conditioning
  • Vending machine
  • Self-serve laundry
  • Multilingual staff
For families
  • Children stay free
  • Free cribs/infant beds
  • Microwave
  • Private bathroom
  • Television
  • Daily housekeeping

Room options

Standard Room, 1 King Bed

  • 300 sq ft
  • Sleeps 2
  • 1 King Bed

Deluxe Room

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

Standard Room, 2 Queen Beds

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 2
  • 1 Queen Bed

About this area

What's nearby

  • In Key West Historic District
  • Duval Street - 3 min walk
  • Mallory Square - 25 min walk
  • South Beach - 1 min drive
  • Southernmost Point - 1 min drive
  • Ernest Hemingway Home and Museum - 2 min drive
  • Higgs Beach - 1 min drive
  • Fort Zachary Taylor Historic State Park - 5 min drive
  • Smathers Beach - 4 min drive
  • Key West Golf Club - 12 min drive

Getting around

  • Key West Intl. Airport (EYW) - 8 min drive


  • Banana Cafe - 4 min walk
  • La Grignote - 4 min walk
  • Louie's Backyard - 4 min walk
  • Santiago's Bodega - 15 min walk
  • Better Than Sex - 6 min walk

About this property

Southwinds Motel

Located 3.2 mi (5.2 km) from the airport, Southwinds Motel puts you 0.1 mi (0.2 km) from Duval Street and 1.3 mi (2.1 km) from Mallory Square. After splashing around at the 2 outdoor pools, you can unwind with a drink at the bar/lounge. Also, this hotel is 1.7 mi (2.7 km) from Smathers Beach. Fellow travelers say good things about the convenient parking.


English, Spanish

Cleaning and safety practices

Enhanced cleanliness measures

Disinfectant is used to clean the property
High-touch surfaces are cleaned and disinfected
Sheets and towels are washed at 60°C/140°F or hotter
Follows industry cleaning and disinfection practices of SafeStay (AHLA - USA)

Social distancing

Contactless check-out
Protective shields in place at main contact areas
Social distancing measures in place

Safety measures

Personal protective equipment worn by staff
Temperature checks given to staff
Temperature checks available for guests
Masks and gloves available
Hand sanitizer provided
Individually-wrapped food options available for breakfast
This information is provided by our partners.

At a glance

Hotel size

  • 58 rooms
  • Arranged over 1 level


  • Check-in time from 4:00 PM - midnight
  • Late check-in subject to availability
  • Minimum check-in age: 18
  • Check-out time is 11 AM

Restrictions related to your trip

  • Check COVID-19 restrictions.

Special check-in instructions

  • Front desk staff will greet guests on arrival

Required at check-in

  • Credit card required for incidental charges
  • Government-issued photo ID may be required
  • Minimum check-in age is 18
  • Minimum Spring Break check-in age is 18


  • Children (13 years old and younger) stay free when occupying the parent or guardian's room, using existing bedding


  • Pets not allowed


  • Wheelchair-accessible parking on site
  • Onsite parking limited

Other information

  • Designated smoking areas
  • No alcohol served onsite

Property amenities

Food and drink

  • Bar/lounge
  • Coffee/tea in a common area

Traveling with children

  • Children stay free (see details)
  • Pool gate

What to do

  • Beach nearby
  • Ecotours nearby
  • Golfing nearby
  • Kayaking nearby
  • Scuba diving nearby
  • Scooter/moped rentals nearby


  • 24-hour front desk
  • Concierge services
  • Tour/ticket assistance
  • Laundry facilities
  • Free newspapers in lobby
  • Luggage storage
  • Multilingual staff
  • Bicycle rentals
  • Beach sun loungers
  • Beach towels
  • Pool loungers
  • Pool umbrellas
  • Romance packages


  • 9 buildings/towers
  • Picnic area
  • 2 outdoor pools


  • Wheelchair-accessible parking

Room amenities

Be entertained

  • 32-inch LED TV
  • Cable TV channels

Home comfort

  • Air conditioning
  • Coffee/tea maker
  • Iron/ironing board
  • Window screens

Sleep well

  • Down comforter
  • Premium bedding
  • Pillowtop mattress
  • Free crib/infant bed

What to enjoy

  • Individually furnished and decorated

Freshen up

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

Stay connected

  • Free local calls
  • Electrical adapters/chargers

Food and drink

  • Refrigerator
  • Microwave
  • Highchair
  • Paper towels


  • Daily housekeeping
  • Access via exterior corridors
  • Cleaning supplies

Special features


Tipsy Rooster - This bar serves light fare only.

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or check-out:
  • Resort fee: USD 20.00 per accommodation, per night
  • Resort fee inclusions:
    • Beach access
    • Beach loungers
    • Beach towels
    • Concierge service
    • In-room coffee
    • Internet access (may be limited)
    • Laundry facilities
    • Parking
    • Partner property beach club access
    • Phone calls (may be limited)
    • Pool access
    • Self parking

Hygiene & cleanliness

This property advises that enhanced cleaning and guest safety measures are currently in place.

Disinfectant is used to clean the property; commonly-touched surfaces are cleaned with disinfectant between stays; bed sheets and towels are laundered at a temperature of at least 60°C/140°F.

Personal protective equipment, including masks and gloves, will be available to guests.

Social distancing measures are in place; staff at the property wear personal protective equipment; a shield is in place between staff and guests in main contact areas; periodic temperature checks are conducted on staff; temperature checks are available to guests; guests are provided with hand sanitizer.

Contactless check-out is available.

Individually-wrapped food options are available for breakfast.

This property affirms that it adheres to the cleaning and disinfection practices of SafeStay (AHLA - USA).


Only registered guests are allowed in the guestrooms.
This property does not have elevators.
Guests can rest easy knowing there's a carbon monoxide detector and a smoke detector on site.
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.

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

Frequently asked questions

Does Southwinds Motel offer free cancellation for a full refund?
Yes, Southwinds Motel does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.
How much does it cost to stay at Southwinds Motel?
As of Sep 30, 2023, prices found for a 1-night stay for 2 adults at Southwinds Motel on Oct 1, 2023 start from $145, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What are the cleanliness and hygiene measures currently in place at Southwinds Motel?
This property confirms that disinfectant is used to clean the property. Furthermore, guests are provided with hand sanitizer, social distancing measures are in place, and staff are given personal protective equipment. Please note that this information has been provided by our partners.
Is there a pool at Southwinds Motel?
Yes, there are 2 outdoor pools.
Are pets allowed at Southwinds Motel?
Sorry, pets aren't allowed.
Is parking offered on site at Southwinds Motel?
Yes. Parking spots may be limited.
What are the check-in and check-out times at Southwinds Motel?
You can check in from 4:00 PM - midnight. Check-out time is 11 AM. Contactless check-out is available.
What is there to do at Southwinds Motel and nearby?
Have fun with activities like boat tours, kayaking, and scuba diving, and practice your swing at the nearby golf course. Additional recreation nearby includes ecotours. Enjoy a swim in one of the 2 outdoor swimming pools or use the hotel's other amenities, which include a picnic area.
What's the area around Southwinds Motel like?
Southwinds Motel is located near Florida Keys Beaches in Key West Historic District, a short 3-minute walk from Duval Street and 3 minutes' walk from South Beach.







Staff & service




Property conditions & facilities




8/10 Very Good

The motel is older, but in decent shape and clean. It is in a convenient location and the staff is great.
3-night trip with friends
Verified guest review

10/10 Exceptional

Pleasantly surprised
We were in #31, with 2 queen beds. Room was quite large with kitchen area of fridge, microwave, small sink and eating bar with 4 barstools. Nice touches like a Mr. Coffee machine with real coffee and a roll of paper towels were much appreciated. Air con was efficient but noisy as all window units are. Wi-Fi good. Out tv didn’t work, we reported it and it was fixed upon our return. Staff good and responsive. Breakfast was all packaged food, as expected but there was plenty of it and the coffee was good. Nothing in Key West is inexpensive but this hotel was on the lower price end for location and I was pleasantly surprised. Friends had a king room at same hotel, not nearly as large. Get the 2 queens. Liquor store on premises did not price gouge.
Karen, 3-night trip with friends
Verified guest review

10/10 Exceptional

Elaine, 1-night trip
Verified guest review

10/10 Exceptional

Friendly staff. Close to the southernmost marker and Fuval street
William, 1-night trip
Verified guest review

4/10 Fair

Hope, 3-night trip
Verified guest review

8/10 Very Good

Room was clean and quiet. The only issue was a spot lot outside the window. Had to use towels to cover window. Light was coming thru blinds while trying to sleep. Staff was very nice to deal with.
Gregory, 2-night trip
Verified guest review

10/10 Exceptional

judith, 2-night family trip
Verified guest review

10/10 Exceptional

Bonnie, 3-night trip with friends
Verified guest review

10/10 Exceptional

Gary, 1-night trip
Verified guest review

8/10 Very Good

Tiny bugs in the bathroom
Steven, 6-night family trip
Verified guest review

General property information

Travelers Say
"Pools were nice, cleaned daily and convenient to any room (3 different pools )."
Reasons to Book
Property Cleanliness & Room Cleanliness
Check-In Time
4:00 PM
Check-Out Time
11:00 AM