All hotels in Key West, Florida, United States of America
1 room, 2 adults

Southwinds Motel, Key West

2-star2 stars
1321 Simonton StreetKey WestFL33040United States of America

Hotel with 3 outdoor pools, near Ernest Hemingway Home and Museum
  • Free WiFi and free parking
  • Collect nightsFor every 10 nights, get 1 free!
Very Good8.0
Great location
Good internet service
Great pool
705See all 705 reviews
From 992 reviewsTripAdvisor Traveller Rating

Southwinds Motel, Key West

from $138
  • Standard Room, 1 Queen Bed
  • Standard Room, 2 Queen Beds
  • Deluxe Room
  • Standard Room, 1 King Bed

At a glance

Key facts

Hotel size

  • This hotel has 58 rooms
  • This hotel is arranged over 1 floor


  • 24-hour check-in
  • Check-out time is 11 AM
After 7 PM, check-in for this property is based at a different location: 1401 Simonton Street, Key West, FL (1/2 block from lobby).

Required at check in

  • Credit card deposit required

  • Government-issued photo ID required

  • Minimum check-in age is 18
  • Minimum Spring Break check-in age is 21

Travelling with others


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

  • No cribs (infant beds)


  • Pets not allowed


  • Free WiFi in public areas

  • Free WiFi in rooms



  • Free self parking (limited)
* See small print for additional details or extra charges

In the hotel

Things to do
  • Bicycle rentals on site
  • Ecotours nearby
  • Golfing nearby
  • Kayaking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scooter/moped rentals nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • 24-hour front desk
  • Concierge services
  • Tours/ticket assistance
  • Laundry facilities
  • Free newspapers in lobby
  • Multilingual staff
  • Number of buildings/towers -
  • Designated smoking areas

In the room

Home comforts
  • Air conditioning
  • Coffee/tea maker
Things to enjoy
  • Individually decorated
  • Individually furnished
Freshen up
  • Private bathroom
  • Shower only
  • Free toiletries
  • Hair dryer
Be entertained
  • 32-inch LED TV
  • Cable TV channels
Stay connected
  • Free WiFi
  • Free local calls
Food and drink
  • Refrigerator
  • Microwave
  • Daily housekeeping
  • Access via exterior corridors

Special features


On Site

  • Bicycle rentals on site


  • Ecotours nearby
  • Golfing nearby
  • Kayaking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scooter/moped rentals nearby
  • Scuba diving nearby
  • Snorkeling nearby

Southwinds Motel, Key West’s small print

Also known as

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


Only registered guests are allowed in the guestrooms.

This property does not have elevators.

Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.

The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation.

Mandatory fees

You’ll be asked to pay the following charges at check in or check out:

  • Resort fee: USD 15.00 per accommodation, per night

Resort fee inclusions:

  • Breakfast
  • Beach access
  • Beach loungers
  • Beach towels
  • Internet access (may be limited)
  • Phone calls (may be limited)
  • Laundry facilities
  • Parking

Inclusions may be listed elsewhere on the page as free or for a surcharge.

Optional extras

We have included all charges provided to us by this hotel. However, charges can vary, for example, based on length of stay or the room you book.

What’s around Southwinds Motel, Key West


  • Ernest Hemingway Home and Museum - 11 min walk
  • Audubon House and Tropical Gardens - 22 min walk
  • Southernmost Point - 24 min walk
  • Mallory Square - 26 min walk
  • Smathers Beach - 31 min walk
  • South Beach - 2 min walk
  • Duval Street - 2 min walk
  • Simonton Beach - 2 min walk

Getting around

  • Key West, FL (EYW-Key West Intl.) - 11 min drive
  • Free self parking
  • Limited parking

Recent reviews

Very Good 8.0 From 705 reviews

Southwinds Motel, Key West
Great place to stay. Only complaint was the floor in the room was filthy. Had to was feet then wear shoes over to the bed to keep feet clean! Once or twice a week they need to mop! Loved the Tipsy Rooster! Loved the area. Just the floor was bad.
Bridgett, us3 night trip
Southwinds Motel, Key West
Very Good8.0
great location, decent value, small/basic but nice
The man who checked me in was nice and helpful getting us acclimated to the area. He also got us fresh towels while dealing with another issue. The late checkout was relayed by a lady at the desk and I thought it quite unreasonable that it would cost the same as an entire additional night if we wanted to checkout a couple hours later.
David, us2 night trip
Southwinds Motel, Key West
Very Good8.0
Florida in May!
The hotel was good for the occasion
david w, us3 night trip
Southwinds Motel, Key West
The answer is yes!
I’ve stayed here several times over the years and I love this place! My room was smaller than other rooms I’ve stayed in but it was perfect for solo travel and when in Key West, you shouldn’t be in the room much! The room was modern, comfy bed, small fridge, great shower. Location is at the southernmost end which I love! It’s a nice walk to the crazy end of town. :) As a 15 year visitor to the island, the cost of hotels has reached ridiculousness, however, the Southwinds remains an affordable gem!
Nancy, us2 night trip
Southwinds Motel, Key West
Very Good8.0
Vintage Key West Motel
This hotel was obviously built a long time ago but is clean and has all the basics. The staff were very nice and helpful. I enjoyed the included coffee, bagels and yogurt for breakfast. The shower head in my unit could use replacing (but it worked). I would have liked a casual chair to sit in too. Otherwise, staying there was a good experience and I would come back.
Dale, us3 night trip

See all reviews

Southwinds Motel, Key West

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