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Southwinds Motel

2.0 star property

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Exterior
2 outdoor pools, pool umbrellas, sun loungers
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Deluxe Room | Terrace/patio
Deluxe Room | Living area | 32-inch LED TV with cable channels, TV

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning

Explore the area

Map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Southernmost Point
    ‪4 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

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

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa 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

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

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Deluxe King Room (Not Pet Friendly) | Bed sheets, alarm clocks

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  • Breakfast included
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4.3 out of 5, Excellent, (1001)
The price is $278
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$333 total
includes taxes & fees
Apr 8 - Apr 9
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About this property

Southwinds Motel

Hotel in Old Town Key West
2 outdoor pools, a bar/lounge, and coffee/tea in a common area are available at this hotel. Continental breakfast is free. Additionally, concierge services, laundry facilities, and a 24-hour front desk are onsite. Housekeeping is available on request.
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.

Southwinds Motel features 2 outdoor swimming pools. A bar/lounge is on site where guests can unwind with a drink. Guests can enjoy a complimentary breakfast each morning.

This Key West hotel also offers a vending machine, multilingual staff, and tour/ticket assistance.

Southwinds Motel has designated areas for smoking.

A complimentary continental breakfast is served each morning between 7:00 AM and 10:00 AM.
Tipsy Rooster - This bar serves light fare only.

Languages

English, Russian, Spanish

Property amenities

Parking and transportation

  • Limited onsite parking
  • Wheelchair-accessible parking available

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
  • Bicycle rentals

Family friendly

  • 2 outdoor pools
  • Highchair
  • 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Wheelchair-accessible parking

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

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children are welcome
Children up to the age of 13 years can stay for free if using existing beds when occupying the parent or guardian's room
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 28.13 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access
  • Self parking

We have included all charges provided to us by the property.

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

8.8

Excellent

Rating 10 - Excellent. 620 out of 1087 reviews
Rating 8 - Good. 286 out of 1087 reviews
Rating 6 - Okay. 117 out of 1087 reviews
Rating 4 - Poor. 43 out of 1087 reviews
Rating 2 - Terrible. 21 out of 1087 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

8/10 Good

rebeca, Miami Beach

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is our 4th time there. It’s in a great area. I really like their complimentary beach chairs and towels. The heated pool was a treat that we also enjoyed everyday on our stay. The ac unit was a little old but overall we had a great time.
Stayed 3 nights in Dec 2024

10/10 Excellent

Jill

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a great find. Loved every part of this property.
Stayed 2 nights in Dec 2024

10/10 Excellent

michael

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Very nice
Stayed 3 nights in Dec 2024

6/10 Okay

Ana

Liked: Cleanliness, staff & service, property conditions & facilities
A little over priced. Breakfast could be better. Hot tub would have been nice for the price
Stayed 2 nights in Dec 2024

6/10 Okay

Khushali

Traveled with family
Stayed 1 night in Dec 2024

8/10 Good

Deanna

Liked: Cleanliness, staff & service, room comfort
Stayed 2 nights in Dec 2024

10/10 Excellent

Phillip

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Dec 2024

8/10 Good

Jennifer

Stayed 2 nights in Dec 2024

8/10 Good

Melody

Traveled with family
Liked: Cleanliness, staff & service
Great location, older motel.Clean but needs update
This is an older, motel style property in a great location. It was clean and the staff were great but the rooms need updating which includes storage and ventilation. The room air was running all the time and left us sweaty and chilly at the same time due to the humidity in the room. There was not a bathroom fan which precluded anything drying. They remind you to reuse your towels but do not provide anywhere to actually hang them where they will dry between uses. We had the shower handle come off, which they fixed right away but the dual handles were tricky to use-needs an update.
This is a king room
Great location
Stayed 3 nights in Dec 2024

10/10 Excellent

Alan

Stayed 2 nights in Oct 2024

6/10 Okay

Soniya

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exhaust fan in bathroom didn't work. Windows in room and bathroom cannot be opened. Small room. Breakfast is all packaged food. There is fresh fruit of bananas and easy to peel orange. Like Tea, drinking water, hot water.
Stayed 2 nights in Dec 2024

6/10 Okay

Kenneth

Disliked: Staff & service
Stayed 3 nights in Dec 2024

8/10 Good

Eleanor

It was ok
Stayed 4 nights in Dec 2024

10/10 Excellent

John

Traveled with group, Traveled with family
Liked: Cleanliness, property conditions & facilities
Always have a great stay there. Great hanging out at the Tipsy Rooster
Stayed 1 night in Dec 2024

8/10 Good

Dulcenea

Traveled with family and small children
Liked: Cleanliness, staff & service
A great way to end our family cruise vacation. Cute vintage property. Rooms are cozy and basic but we didn’t spend much time inside. Walking distance to the beach, the southernmost point, and Duval. Anna’s coffee and the food truck across the street are amazing! The free Duval loop bus stop is close as well as the trolley stop. Would stay again!
Stayed 2 nights in Dec 2024

6/10 Okay

Crystal, Lakeport

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities
Stayed 3 nights in Dec 2024

10/10 Excellent

Chuck

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice motel and close to Duvall St
Stayed 3 nights in Dec 2024

6/10 Okay

Christina M

Traveled with family
Liked: Staff & service
Unfortunately our room was directly Next to the rooster bar and we heard the people In there and the music well into 3am every night - made for very poor sleeping conditions. Also when showering the hot and cold handles did not work, made for very cold Showers which was really too bad, wouldn’t recommend or stay here again
Stayed 2 nights in Dec 2024

8/10 Good

Kelly

Traveled with group
The music at night
Stayed 3 nights in Dec 2024

10/10 Excellent

Deborah, Woburn

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This is our second stay at southwinds. Great place to stay.
Stayed 1 night in Dec 2024

4/10 Poor

Patrick, Richmond Hill

Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
The exterior door of the room was a hollow wood door. Hollow wood doors are intended for interior use such as closets, bathrooms, etc., not exterior. For proper security, an exterior door should be either metal or solid wood. Even though the door on the room I stayed in had two locks, including a dead bolt, a hollow wood door can be broken open in minutes, if not seconds, with ordinary common hand tools or it can be kicked apart. This is a serious security lapse. Additionally, there was a gap between the bottom of the door panel and the threshold that likely permitted a large cockroach that I found in the room on my third night there to gain access to the room. Someone at the front desk told me that the roaches live in the trees outside so it probably got in under the door. It would seem that if they knew about the roaches, measures should have been taken (such as better fitting doors with barriers along the bottoms) to keep them out of the rooms. Other possible intruders, such as mice, could probably squeeze through too. Other issues that I noticed didn't seem well thought out such as the location of the wall mounted TV; most of the screen could not be seen from the bed if the outward swinging bathroom door was open by more than about a foot. It could have been mounted elsewhere. Overall, the room was clean, the bed was comfortable and the air conditioner worked well. Everything worked well in the bathroom though the sink faucet was a bit loose and moved slightly.
Stayed 4 nights in Dec 2024

8/10 Good

Molly

Traveled with group
Great place
Cute place. Quiet. Great location. 2 pools.
Stayed 3 nights in Dec 2024

8/10 Good

Eric

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice older property, walking distance to Duval street. Great bar next to the property with live music.
Stayed 2 nights in Dec 2024

8/10 Good

Cynthia, Hamilton

Traveled with family
Air conditioner comes on and shuts off every 2 minutes. Very loud water pressure was great for cold water. Hot water trickled
Stayed 2 nights in Dec 2024

10/10 Excellent

Norbert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quint little cottages
Stayed 1 night in Dec 2024