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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

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

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • 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
(108 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

Located in Old Town Key West, Southwinds Motel is adjacent to South Beach and within a 5-minute walk of other popular sights like Duval Street. This 58-room hotel welcomes guests with 2 outdoor pools, free breakfast, and a bar/lounge.

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

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬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

Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. Self parking is offered for USD 22.50 per day. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. Additional amenities include laundry facilities, a picnic area, and a vending machine.
Guests can expect to find 32-inch LED TVs with cable channels. Bathrooms offer hair dryers and free toiletries, and pillowtop beds with premium bedding and down comforters ensure a restful night. Other standard amenities include refrigerators, microwaves, and coffee makers. Housekeeping is available on request.
2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

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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

  • This property doesn't allow pets

Children and extra beds

  • Free cribs/infant beds are available

Property payment types

Important information

Fees

You'll be asked to pay these 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

These are all of the charges provided to us by the property.

Optional extras

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

  • Self parking fee: USD 22.50 per day

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM—-midnight
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day. Driving? This property offers parking (fees apply).

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • The minimum check-in age for Spring Break is 18 years old.
  • This property accepts credit cards, debit cards, and cash.
  • The credit card used at check-in for incidentals must be in the name of the primary guest who made the reservation.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Additional information about polices, regulations, and more:

  • Registered guests are the only ones allowed in guestrooms.
  • No alcohol is served at Southwinds Motel.
  • There are no elevators.
  • No rollaway or extra beds are available.

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

Is a free cancellation option available at Southwinds Motel?

Southwinds Motel offers free cancellation on some room rates. For specific requirements, look at the cancellation policy on Orbitz.

How much does it cost to stay at Southwinds Motel?

As of May 4, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Jun 1, 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.

What's there to do around Southwinds Motel?

This hotel is situated in Old Town Key West, just steps from Florida Keys Beaches and Duval Street, and within a short walk of South Beach. You'll also find Southernmost Point and Ernest Hemingway Home and Museum less than a mile away.

Will I be able to park at Southwinds Motel?

Yes, parking is offered for USD 22.50 per day.

Does Southwinds Motel have a casino at the property?

No, Southwinds Motel doesn't have a casino.

Will I find an indoor pool at Southwinds Motel?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools.

Is Southwinds Motel a good place to stay for couples?

There are plenty of amenities for couples at this hotel, including 2 outdoor pools, proposal/romance packages, and a bar/lounge.

Does Southwinds Motel have a hot tub?

No, this hotel doesn't have a spa tub.

Does Southwinds Motel feature a restaurant that includes a breakfast menu?

Yes, Southwinds Motel serves free continental breakfast at Tipsy Rooster each morning.

Will Southwinds Motel allow pets to stay free of charge?

No, pets aren't allowed at Southwinds Motel.

Does Southwinds Motel have connecting rooms available?

No, there aren't connecting guestrooms at this hotel.

How close is the airport from Southwinds Motel?

The closest major airport to Southwinds Motel is Key West Intl. Airport (EYW), which is 3.2 mi away (8 minutes by car).

Can I book a room with a balcony at Southwinds Motel?

No, you won't find guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 731 out of 1323 reviews
Rating 8 - Good. 356 out of 1323 reviews
Rating 6 - Okay. 149 out of 1323 reviews
Rating 4 - Poor. 59 out of 1323 reviews
Rating 2 - Terrible. 28 out of 1323 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

8/10 Good

Steven

Liked: Cleanliness, staff & service, amenities
Great place - can walk to most activities- place a bit dated - decent breakfast- staff super friendly- would stay again.
Stayed 2 nights in Apr 2026

10/10 Excellent

Shawn

Stayed 1 night in Dec 2025

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

10/10 Excellent

Aaron

Stayed 1 night in Jan 2026

6/10 Okay

Robert

Traveled with partner
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
Room was ok, small but clean. Location was good, easy access to the beach, Duval, about a 35 min walk to the west side and port. Used to be free parking but now are charging. Not sure what the resort fee paid for outside of the pool. Downside. Staff was not friendly or helpful. Acted as if we were inconveniencing them the entire week we were there. Complimentary breakfast was pretty weak. No hot water on our last day/night. Pretty loud each evening with the band in the bar anywhere from 6pm to past 10 depending on the evening - felt like they were in our room on a couple of nights. First trip to Key West and our stay here was disappointing. Would not come back to this facility.
Stayed 7 nights in Jan 2026

10/10 Excellent

Lucy

Traveled with partner
Liked: Amenities
Everyone was nice and courteous. Quiet place. Really enjoyed our weekend
Stayed 3 nights in Jan 2026

8/10 Good

Susie

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very clean. Great location. Small rooms. WiFi did not work very well in our room (#5). But we would stay here again.
Stayed 3 nights in Jan 2026

8/10 Good

Frederick

Traveled with partner
Liked: Cleanliness, staff & service, amenities
Very low water pressure. Showing it's age
Stayed 2 nights in Jan 2026

4/10 Poor

Robin

Stayed 1 night in Jan 2026

8/10 Good

Tom

Traveled with pets, Traveled with family
Liked: Cleanliness, property conditions & facilities
The room was nice, clean and comfortable. It was a bit small as we travel with our little dogs, however it had a great bed. The faucet and shower controls should be replaced as it was very difficult to adjust the temperature on both. The staff was great and the breakfast was the best. Value was worth the price.
Stayed 3 nights in Jan 2026

10/10 Excellent

James

Liked: Amenities
Old Needs updating Great location Friendly staff
Stayed 4 nights in Jan 2026

6/10 Okay

steve

Stayed 2 nights in Jan 2026

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