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Southwinds Motel

2.0 star property
Hotel near Duval Street in Key West

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Photo gallery for Southwinds Motel

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

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Parking available
  • Bar

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.)
    ‪11 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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About the neighborhood

Key West

Old Town Key West stay.A stay at this Old Town Key West hotel places you steps from South Beach and within a 5-minute walk of Duval Street. Southernmost Point and Ernest Hemingway Home and Museum are also within half a mile (1 km).

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

Hotel near Duval Street in Key West
Southwinds Motel offers its guests 2 outdoor swimming pools. You can enjoy a drink at the bar/lounge. Free breakfast is available daily.

A vending machine, multilingual staff, and tour/ticket assistance are also featured at Southwinds Motel. For a fee, parking is available.

Smoking is allowed in designated areas at this Key West hotel.

  • 1 floor
  • 58 guestrooms or units
  • 9 buildings
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Coffee in lobby
  • Self-service laundry
  • Front desk (24 hours)
  • Staff is multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Outdoor picnic space
  • Newspapers in lobby (free)
  • Smoking in designated areas
  • Bar or lounge
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.

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Wicker Guesthouse
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  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 1,014 reviews
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The price is $229
May 14 - May 15
Total with taxes and fees
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Property amenities

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room crib
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate

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

Things to do

  • 2 outdoor pools

Accessibility

  • No elevator

Room amenities

Entertainment

  • 32-inch LED TV with cable channels

Bedroom

  • Down comforter
  • Free crib
  • Pillowtop mattress
  • Premium bedding

Bathroom

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

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

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Free cribs (infant beds)!

Property payment types

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • 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've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Self parking fee: USD 22.50 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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 Visa, Mastercard, American Express, Discover, Diners Club, debit cards, and cash. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.
  • Alcohol isn't served at Southwinds Motel.

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

Frequently asked questions

How close is Southwinds Motel to the airport?

Southwinds Motel is 3.2 mi (8-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

How much does it cost to stay at Southwinds Motel?

As of May 11, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Jun 2, 2026 start from $218, including 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.

Does Southwinds Motel have an airport shuttle?

Airport shuttle services are not available at Southwinds Motel.

How close is Southwinds Motel to the beach?

This hotel is a short 3-minute walk from South Beach and 11-minute walk from Clarence S. Higgs Memorial Beach Park. Don't forget your sunscreen!

Does Southwinds Motel offer free breakfast?

Southwinds Motel offers free continental breakfast every day from 7:00 AM to 10:00 AM.

Is there a casino at Southwinds Motel?

No, there is no casino at this hotel.

What time is check-in at Southwinds Motel?

Check-in start time: 4:00 PM; Check-in end time: midnight.

Is there free parking at Southwinds Motel?

Free parking is not available at this hotel. Self parking is available for USD 22.50 per day.

Does Southwinds Motel have a pool?

Southwinds Motel features 2 outdoor pools.

Does Southwinds Motel have a restaurant?

Southwinds Motel is home to Tipsy Rooster, which features light fare.

Does Southwinds Motel have a spa?

There are no spa services available at this hotel.

How close is Southwinds Motel to downtown Key West?

Southwinds Motel is 0.6 mi away from Key West.

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 741 out of 1337 reviews
Rating 8 - Good. 358 out of 1337 reviews
Rating 6 - Okay. 151 out of 1337 reviews
Rating 4 - Poor. 59 out of 1337 reviews
Rating 2 - Terrible. 28 out of 1337 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

10/10 Excellent

KIMBERLY, Whippany

Traveled with partner
Liked: Cleanliness, staff & service, amenities
This is a good clean place to stay. Definitely outdated and old. However we didn’t mind that as it had huge rooms, was very quiet (stayed in back rooms) and super convenient to walk everywhere we needed to go. Breakfast was just very basic and had to eat in room. That was ok with us and met our needs. Only issue is that the room could use a “real” chair to sit in. Only had bar stools by a counter and for elderly people this was difficult. The chairs and towels by the beach were ok but obviously this wasn’t the best beach. Ok for kids and to sit. nice perk.
Stayed 2 nights in Apr 2026

10/10 Excellent

CONNIE, Ballwin

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel, clean and excellent location.
Stayed 2 nights in Mar 2026

4/10 Poor

Wanda

Traveled with partner
Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
This property is very conveniently located in the Old Town section of Key West. The staff was very nice and helpful. However, this place is in serious need of an upgrade and remodel. I didn't expect to see paint peeling off the walls at a property that charges over $400 per night and adds on a $33 per night "resort fee."
Stayed 2 nights in Mar 2026

10/10 Excellent

JD

Stayed 3 nights in Oct 2025

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

8/10 Good

Khristie

Liked: Cleanliness, amenities
Clean spacious room with good amenities. Staff was adequate. Housekeeping only every 3 days and they didn't bother to show them.
Stayed 6 nights in Jan 2026

4/10 Poor

Anna, State College

Traveled with group
Disliked: Amenities, property conditions & facilities
Pictures did not reflect the condition of the motel. It was in need of an overhaul and our room had the bare minimums - very limited. . . had to unplug the coffee maker to plug in the microwave. Wouldn't stay there again.
Stayed 5 nights in Jan 2026

8/10 Good

Louis

Traveled with family
Liked: Cleanliness
Location
Stayed 3 nights in Jan 2026

10/10 Excellent

Brandy Lynn

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Super cute! Perfect location. We would stay again.
Stayed 3 nights in Jan 2026

10/10 Excellent

Sherri

Liked: Cleanliness, staff & service, amenities
Wonderful room by the pool. Excellent staff, great location to be able to walk just about anywhere on the island.
Stayed 1 night in Jan 2026

8/10 Good

Sherri

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Southwinds is an older motel in the heart of Key West. Easy to walk just about anywhere from their location. Room was clean, great bed and wonderful staff. Only problem was that we were close to the bar, so lots of loud music at night. We didn’t complain or ask to be moved as we were there during the KW Marathon, and all the rooms were full. We did add an extra day to our stay, and they placed us in a great room by the heated pool. Would definitely stay there again, just not close to the bar.
Stayed 3 nights in Jan 2026

6/10 Okay

Nancy

Traveled with group
It was a shabby mitel
Stayed 1 night in Jan 2026

10/10 Excellent

JOHN, milford

Stayed 1 night in Jan 2026

6/10 Okay

Jeffrey

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Clean room, but no black out drapes or shades. The lights on the building shine in the room. Staff was great and Tipsy Rooster is a great place to hang out.
Stayed 5 nights in Jan 2026