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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
Reception
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Property grounds
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
(106 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
(78 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
(112 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
  • ‪Banana Cafe - ‬4 min walk
  • ‪Southernmost Point Bar in the USA - ‬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 concierge services 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 Mar 31, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Apr 26, 2026 start from $338, 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 Duval Street and Florida Keys Beaches, 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.

Is parking available on site 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.

What will couples enjoy most about a stay at Southwinds Motel?

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

Are there hot tubs at Southwinds Motel?

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.

Are there connecting rooms at Southwinds Motel?

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).

Are there rooms with balconies at Southwinds Motel?

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

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 721 out of 1296 reviews
Rating 8 - Good. 347 out of 1296 reviews
Rating 6 - Okay. 147 out of 1296 reviews
Rating 4 - Poor. 57 out of 1296 reviews
Rating 2 - Terrible. 24 out of 1296 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Shawn

Stayed 1 night in Dec 2025

10/10 Excellent

Mary

Stayed 3 nights in Dec 2025

6/10 Okay

Anil

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Roo. Was good and well maintained ,
Stayed 1 night in Dec 2025

8/10 Good

kelly

Stayed 2 nights in Dec 2025

10/10 Excellent

Bea, Onalaska

Stayed 7 nights in Dec 2025

10/10 Excellent

Diane

Stayed 1 night in Dec 2025

10/10 Excellent

john, AUSTIN

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Charming cottages 1 block from beach, next to Tippsey Rooster Bar live music, with small store and deli across the street. Best Spicy Cuban sandwich.
Stayed 2 nights in Dec 2025

6/10 Okay

Shandolyn

Disliked: Cleanliness, property conditions & facilities, room comfort
Super small bathrooms. Do not rent motel is you are over 250 pounds due to small bathroom and shower. Breakfast was offered but I did expect waffles or more hot options. Connected to liquor store and bar with live music which was nice. Front desk not knowledgeable of local amenities or landmarks. Also bathroom was not cleaned to me liking at all. Hair and stuff in the shower
Stayed 3 nights in Dec 2025

10/10 Excellent

Cheryl

Traveled with group
Liked: Cleanliness, staff & service, amenities
This hotel is very old but clean and comfortable. The people are very nice and helpful. The location is very close to the beach and southernmost point marker.
Stayed 1 night in Dec 2025

4/10 Poor

Thomas, Warwick

Put us in a room right next to bar that had extremely loud music till 1-2 AM, also outside lights on all night and it was like daytime in the room, even with blinds closed, no drapes, made reservations for 2 rooms months earlier and our friends were the farthest room away from us
Stayed 2 nights in Dec 2025

6/10 Okay

Crystal

Traveled with partner
Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
The room is small but clean with everything you need. The hotel is very cute. The evening staff was extremely rudechecknin was rud
Stayed 1 night in Dec 2025

10/10 Excellent

Gaston

Liked: Cleanliness, amenities, property conditions & facilities
Great location and well maintained. Breakfast does the job.
Stayed 1 night in Dec 2025

8/10 Good

Susan

Traveled with family
Liked: Cleanliness, staff & service, amenities
Overall the place was nice, you could tel they try hard to make it nice. They could dim the outdoor lights a little in the evening so they don't come through the blinds at night time though! The evening clerk wasn't very cheery...at all. She was there LOL Breakfast is basically wrapped pastries, fruit and yogurt, juice.....really a continental breakfast. We decided to pass and go to Frenchies!! YUM! The rooms were clean, beds were firm, pillows were decent and plentiful. We only stayed a night, but that's all i'd really stay for if it were a longer vacation i'd stay somewhere else. They hit you with a $30 service fee and another $25 for something else right when you check in....so be aware of that. We did book through Expedia. You can hear people knocking on other doors...thinking it might be your own....BUT as I said it was one night, the price was right until we got hit with the other fees.... Clean, safe, and close to the southernmost point and Dumont st.
Stayed 1 night in Dec 2025

10/10 Excellent

Denna

Traveled with family
Liked: Cleanliness, property conditions & facilities
Cute comfortable rooms great staff and great location!! Will stay again
Stayed 1 night in Dec 2025

10/10 Excellent

William

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great location. Decent facilities. Wonderful staff. Not a bad price considering key west.
Stayed 2 nights in Dec 2025

2/10 Terrible

Rosalind

Disliked: Cleanliness
Stayed 1 night in Dec 2025

8/10 Good

Charles

Liked: Staff & service, room comfort
Did not eat breakfast there
Stayed 2 nights in Dec 2025

10/10 Excellent

THERESA

Liked: Cleanliness, amenities, property conditions & facilities
Staffs are friendly. The room is clean and breakfast is fantastic
Stayed 1 night in Dec 2025

8/10 Good

anna

Liked: Cleanliness, staff & service, amenities
Clean nice motel
Stayed 6 nights in Dec 2025

10/10 Excellent

Stefanie J

Liked: Cleanliness, staff & service, amenities
The room was great, and the staff was so helpful. It is at a great location. It offers free parking, which is wonderful!
Stayed 3 nights in Dec 2025

10/10 Excellent

darrin

Liked: Cleanliness, amenities, property conditions & facilities
Staff was great
Stayed 3 nights in Dec 2025

10/10 Excellent

Adam

Stayed 3 nights in Dec 2025

6/10 Okay

April, Wood Dale

Traveled with partner
Air conditioner broke. Water on the floor. Service man was helpful with the tv not working and moving us to another room. Pool temp was nice.
Stayed 1 night in Dec 2025

10/10 Excellent

Lisa

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Our stay at Southwinds hotel was wonderful. The staff always treats as courtesy since we booked through orbits we were allowed to pick our room once we arrive there great place to stay great pick up and go breakfast in the morning and close to several fun activities.
Stayed 7 nights in Dec 2025

10/10 Excellent

Linda

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Room was clean, staff was very nice. Breakfast offered was basic but fine. Location was perfect with Tipsy Rooster Liquor Store and bar next door. The store across the street was an extra bonus.
Stayed 7 nights in Nov 2025

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