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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Exterior
Exterior
Property grounds
2 outdoor pools, pool umbrellas, sun loungers
Reception

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar
$316
includes taxes & fees
Jan 5 - Jan 6, 2026

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.)
    ‪7 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
(98 reviews)
  • 250 sq ft
  • 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
(73 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
(106 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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Property grounds
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4.4 out of 5, Excellent, 1,003 reviews
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About this property

Southwinds Motel

Hotel in Old Town Key West
2 outdoor pools, a bar/lounge, and self parking are available at this hotel. Continental breakfast is free. Other amenities include coffee/tea in a common area, concierge services, and laundry facilities. 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. Onsite parking is available (surcharge).

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.

Property amenities

Parking and transportation

  • Self parking on site (USD 22.50 per day)
  • Limited onsite self parking

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
  • 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

8.8

Excellent

Rating 10 - Excellent. 723 out of 1244 reviews
Rating 8 - Good. 322 out of 1244 reviews
Rating 6 - Okay. 129 out of 1244 reviews
Rating 4 - Poor. 51 out of 1244 reviews
Rating 2 - Terrible. 19 out of 1244 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

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Hotel is amazing has everything you need. Pools are clean. Service is amazing
Stayed 4 nights in Sep 2025

10/10 Excellent

Ross

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Sep 2025

10/10 Excellent

Walter

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
The room was nice, & the area was fairly good. Near the Southernmost Point marker. Only downside was the water pressure was pretty weak.
Stayed 2 nights in Sep 2025

10/10 Excellent

Terrie

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Sep 2025

6/10 Okay

Huang

Traveled with partner
overall it is good
Stayed 1 night in Sep 2025

10/10 Excellent

Fernando

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent for the prize
Stayed 2 nights in Sep 2025

8/10 Good

Ronald

Stayed 4 nights in Jul 2025

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Traveler

Very nice and cozy, would definitely stay again for sure!!!
Stayed 2 nights in Sep 2025

4/10 Poor

Carmella

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities, room comfort

Resort fees without resort amenities.

What we liked: Big shower, nice staff What we didn’t like: Very small room, no water pressure, large gap in door to outside(plenty of room for bugs to join us in the room), tight parking. No servicing of room during a three day stay. One night it rained and we waded ankle deep in water to the car. Can’t figure out what we paid a resort fee for!
Stayed 3 nights in Sep 2025

8/10 Good

Suzanne

Liked: Staff & service
Stayed 3 nights in Sep 2025

10/10 Excellent

Riley

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My son and his girlfriend drove down for a quick weekend and the keys and stayed here. They loved that they could walk everywhere from their hotel. It was super convenient to everything they wanted to do and they said they would stay there again.
Stayed 3 nights in Aug 2025

8/10 Good

Daile M

Traveled with family
Liked: Cleanliness, staff & service, room comfort

Good budget stay in convenient location

As far as key west is concerned, this is a great budget hotel and easy walking to most places touristy. We based our stay here on using the e scooters on site to get around and had all kinds of issues which was unfortunate. The breakfast included was great. I do have an odd charge to follow up on with the hotel
Stayed 2 nights in Aug 2025

10/10 Excellent

Tonya

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Will stay again

This was my 2nd time at Southwinds and it did not disappoint. The room was clean, bed was comfortable. Location is great. They even provided early check in at no additional cost.
Stayed 3 nights in Sep 2025

10/10 Excellent

David

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Aug 2025

2/10 Terrible

Levi

Traveled with family
Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
The staff was kind, not the issue. The room I booked did not look like the room I got. Everything was severely outdated. The shrubbery getting into the room was blocking portions of the door, not just my room but others too. There was nowhere to sit because the two chairs that were in there are badly soiled. There’s a sticker on the mirror stating to conserve the environment only towels that we put on the floor will be cleaned. The towels that were hung up were shredded and looked like someone has been using them so my daughter didn’t feel comfortable showering in there. There was also bugs in the bathroom. The breakfast they offer are expired muffins and pastries that were hard. They should be ashamed of themselves for charging over $200 for a night in a place like this.
Stayed 1 night in Sep 2025

10/10 Excellent

Donna

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
the staff was so helpful the room was clean my husband met so many people at the local bar and he seen people he met the year before we try to stay in the same place ever year we will be coming back next year
Stayed 1 night in Sep 2025

10/10 Excellent

Terri

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Enjoyed the stay

Everything was clean, staff was friendly and a great location
Stayed 2 nights in Sep 2025

8/10 Good

Denise

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great stay

Great location. Place was clean and neat. Leary about motels but this one was very nice. Didn't get to use all the amenities. Would suggest.
Stayed 1 night in Sep 2025

10/10 Excellent

Stacie

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Safe and chill atmosphere with parking, convenient food, beverages, and market onsite.
Stayed 2 nights in Aug 2025

8/10 Good

Robert

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The property was decent for the price. Staff was not overly friendly. It was great for the amount of time we spent actually on Property.
Stayed 3 nights in Aug 2025

10/10 Excellent

Christine

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Aug 2025

10/10 Excellent

Craig

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect spot! One block off of Duvaul St..Walking distance to the Famous "Lowest spot", Close to beaches, Close to golf cart rentals to drive around Key West! Loved it
Stayed 2 nights in Aug 2025

10/10 Excellent

Jason

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great rooms with great views!
Stayed 3 nights in Aug 2025

8/10 Good

Stephen

Stayed 4 nights in Aug 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
Older property but was perfect for what we needed.
Stayed 1 night in Aug 2025