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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
Front of property
Property grounds
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Reception

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Parking available
  • Bar
The current price is $207
$184 nightly
$207 total
Total with taxes and fees
May 19 - May 20

Explore the area

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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.)
    ‪12 min drive‬

Room options

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
(109 reviews)
  • 250 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 Queen 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
(80 reviews)
  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

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, 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
(115 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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Total with taxes and fees
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About the neighborhood

Key West

With a stay at Southwinds Motel in Key West (Old Town Key West), you'll be steps from South Beach and 3 minutes by foot from Duval Street. .This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.

What's nearby

  • Duval Street - 3 min walk - 0.2 miles
  • South Beach - 3 min walk - 0.2 miles
  • Southernmost Point - 5 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles

Getting around

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

Restaurants

  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 min walk

About this property

Southwinds Motel

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.

Make yourself at home in one of the 58 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with down comforters and premium bedding. 32-inch LED televisions are provided, with cable programming available. Private bathrooms with showers feature complimentary toiletries and hair dryers.
Make use of convenient amenities such as concierge services, a picnic area, and a vending machine.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:00 AM to 10:00 AM.
Featured amenities include complimentary newspapers in the lobby, a 24-hour front desk, and multilingual staff. Self parking (subject to charges) is available onsite.
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

  • Self parking on site (USD 22.50 per day)

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 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

  • No elevator

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

Information provided by the property may be translated using automated translation tools

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 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 have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 22.50 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

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

8.6

Excellent

Rating 10 - Excellent. 747 out of 1351 reviews
Rating 8 - Good. 362 out of 1351 reviews
Rating 6 - Okay. 153 out of 1351 reviews
Rating 4 - Poor. 60 out of 1351 reviews
Rating 2 - Terrible. 29 out of 1351 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Debra

Traveled with family
Liked: Cleanliness, staff & service, amenities
Best place for price. Love rooms 1 and 2
Stayed 2 nights in Jan 2026

8/10 Good

Leah

Stayed 3 nights in Feb 2026

6/10 Okay

OSCAR

Liked: Cleanliness, staff & service
Not sure why this place charges a “resort fee” upon check in (I was charged $156 for three nights). This is an old motel with many upgrades and improvements needed. My positive is that everyone at the front desk was helpful and friendly
Stayed 3 nights in Feb 2026

10/10 Excellent

Laura

Liked: Cleanliness, amenities, property conditions & facilities
Clean rooms, hot showers, friendly staff, great location! The Tipsy Rooster was a bonus 🙂
Stayed 7 nights in Feb 2026

8/10 Good

JANET

Traveled with partner
Liked: Cleanliness
Location to Duvall street and other sites.
Stayed 2 nights in Feb 2026

8/10 Good

Kristin

Liked: Cleanliness, property conditions & facilities
Allowed to store luggage for the day
Stayed 2 nights in Feb 2026

8/10 Good

Michael L

Liked: Cleanliness
Location
Stayed 14 nights in Jan 2026

8/10 Good

Robert, Springfield

Stayed 5 nights in Feb 2026

10/10 Excellent

JD

Stayed 3 nights in Oct 2025

8/10 Good

Stacy

Stayed 3 nights in Feb 2026

10/10 Excellent

Judy

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The room was very nice and had everything we needed. Checking in and out was so quick and easy with very friendly employees. The breakfast was excellent with plenty of good choices. The location was great with easy walk or bike ride to most things.
Stayed 4 nights in Feb 2026

8/10 Good

Grady

The rooms were clean, the staff was polite and helpful, and the provided light breakfast options provided were good.
Stayed 7 nights in Feb 2026

10/10 Excellent

Valerie

Liked: Cleanliness, amenities, property conditions & facilities
Friendly and helpful staff.
Stayed 8 nights in Jan 2026

10/10 Excellent

Deborah

Liked: Cleanliness, amenities, property conditions & facilities
Great location and comfortable stay.
Stayed 3 nights in Feb 2026

8/10 Good

Thomas

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Older motel, rooms are kinda small but everything was clean, staff was great, even had free use of laundry facilities, decent breakfast selection with nearby options also available.
Stayed 7 nights in Feb 2026

6/10 Okay

Hunter

Stayed 7 nights in Feb 2026

8/10 Good

William

Stayed 1 night in Feb 2026

8/10 Good

Shelly

Traveled with group
Liked: Cleanliness, amenities
Rooms were clean. The bed need replaced. The area was great.
Stayed 8 nights in Jan 2026

6/10 Okay

Jimmy Ray

Liked: Cleanliness, amenities, property conditions & facilities
The staff was courteous. We did change rooms due to no dresser. We did not want to live out of our suitcase for a 7 night stay. And There were only stools in the room which was not safe for us at our age. The continental breakfast was great.
Stayed 8 nights in Jan 2026

10/10 Excellent

Chris

Liked: Cleanliness, amenities, property conditions & facilities
Our room was somewhat dated but nontheless fit our needs for the long weekend. Great location. Its not fancy but very adequate.
Stayed 4 nights in Jan 2026

10/10 Excellent

Kimberly

Wonderful location, had everything we needed!
Stayed 3 nights in Jan 2026

6/10 Okay

Sally

Liked: Staff & service
This was the most expensive hotel on our road trip - including a Universal Resort hotel. The front desk ladies were friendly, helpful and welcoming. The location very good, few minutes from Duval Street and Southernmost point. Plenty of bars and restaurants all within walking distance. Sadly the room we had (71) nothing like the picture shown. It looked more like a forgotten staff room at the end of the car park. No wardrobe, tiny and dated, didn’t feel particularly clean. The bedsheets were stained so we had to ask for them to be changed. The bathroom was incredibly dated and the toilet seat in dire need of a new one - it was chipped and stained yellow. Horrible. PLEASE replace it! Overall very disappointing and we wouldn’t stay here again. Outrageously expensive for a very sub standard motel.
Stayed 2 nights in Jan 2026

10/10 Excellent

Karen

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff
Stayed 4 nights in Jan 2026

8/10 Good

Bryan

Traveled with group, Traveled with partner
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