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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Pool
  • Air conditioning
$169
includes taxes & fees
Aug 25 - Aug 26

Explore the area

View in a map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Southernmost Point
    ‪5 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Room options

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | 1 bedroom, premium bedding, down comforters, pillowtop beds

Standard Room, 1 King Bed

8.4 out of 10
Very good
(101 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

1 bedroom, premium bedding, down comforters, pillowtop beds

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, 2 Queen Beds

Standard Room, 2 Queen Beds | 1 bedroom, premium bedding, down comforters, pillowtop beds

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(65 reviews)
  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

1 bedroom, premium bedding, down comforters, pillowtop beds

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(88 reviews)
  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

Similar properties

Property grounds

The Palms Hotel

  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
4.3 out of 5, Excellent, 1,000 reviews
The Palms Hotel

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
  • 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

  • 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. 671 out of 1157 reviews
Rating 8 - Good. 293 out of 1157 reviews
Rating 6 - Okay. 127 out of 1157 reviews
Rating 4 - Poor. 49 out of 1157 reviews
Rating 2 - Terrible. 17 out of 1157 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

6/10 Okay

amber

Stayed 5 nights in May 2025

10/10 Excellent

Paul

Liked: Cleanliness, amenities, property conditions & facilities
Nice place. Clean. Nice pools. Close to amenities
Stayed 1 night in May 2025

6/10 Okay

Edward

Stayed 4 nights in May 2025

8/10 Good

Leonard Cour

Stayed 4 nights in May 2025

8/10 Good

John

Stayed 2 nights in May 2025

8/10 Good

CARRIE

Traveled with partner
Liked: Cleanliness, amenities
The hotel was great for our stay, walkable to Duvall, a little far to the hot spots on Duval, which was fine for us. Scooter rental was totally worth it. Didn’t use the pools, the bar was cool, nice area. Free parking. The bathroom was tiny and there was no where to put shower toiletries, but it worked for two people. Would stay there again!!
Stayed 4 nights in May 2025

10/10 Excellent

Anne-Marie

Liked: Cleanliness
Close to the beach!
Stayed 2 nights in May 2025

10/10 Excellent

Andrew

Business traveler
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in May 2025

10/10 Excellent

mark

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic location Friendly staff. Has a decent pool. Really good breakfast ( wasn’t hot but still had excellent choices) There is a bar next door which has a singer on at various times Overall really good option
Stayed 1 night in May 2025

6/10 Okay

lee

Traveled with family
Liked: Cleanliness, staff & service
Very small room
Stayed 2 nights in May 2025

10/10 Excellent

janice

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very convenient location. Had everything we needed.
Stayed 3 nights in May 2025

6/10 Okay

Deborah

Traveled with family
Stayed 4 nights in May 2025

10/10 Excellent

Kristie

Stayed 3 nights in May 2025

6/10 Okay

Hallie

Traveled with group
Liked: Cleanliness
Disliked: Staff & service
The workers were quite literally the only damper. We were told we would have housekeeping come every 3 days. When the 3rd day came, we put our towels out on the floor to be picked up. When we came back the room was still not cleaned and dirty towels still there. Went to desk the next day to ask about housekeeping and when we told them they never came they said “that’s not good.” Oh? So then we asked for towels so we could at least shower. We were told no housekeeping was on the way. After 30 min we called and were told housekeeping was coming. Housekeeping came and we were kicked out of our room so they could clean, again all the while we were waiting all we wanted was clean towels so we could shower and leave for the day. When I asked for again shower towels days later I was given a beach pass? I asked “how does this get us shower towels?” Then the worker laughed and said she blunt I said “beach pass” ok idk how you get beach pass from shower towels but ok. Maybe look into retraining people who don’t know left from right.
Stayed 8 nights in Apr 2025

8/10 Good

Penni

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice
Stayed 1 night in May 2025

10/10 Excellent

Tammy A

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Close to beach
Stayed 4 nights in Apr 2025

10/10 Excellent

Keith

Liked: Cleanliness, staff & service, property conditions & facilities
Location The motel is well situated only a block away from a small sandy beach and a couple of blocks away from the "southern most point", in downtown Key West. There is a free hop on hop off "Duval loop" bus service that runs every 30 minutes or so. Motel It reminds me of something out the 1950's, (in a good way) but with up to date additions like WiFi etc. The room we had was small but perfectly presented. Check-in was smooth and staff were lovely. Package came with breakfast, which was nice with a good selection & kept restocked. The pool was in good order with free pool towels. There are a number of places to eat around and about (our best find for a quick bite was a catering truck right opposite the motel, good size burger & fries for not much money)
Stayed 2 nights in May 2025

10/10 Excellent

Renee

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was exactly the old Florida feel I was looking for and delivered on quaintness and retro excellence. For the age of the property it was very well maintained and clean. The rooms were large and I loved the mini fridge and microwave. The staff were incredibly friendly and the location could not be beat. Everything I was hoping it would be and more
Stayed 1 night in May 2025

10/10 Excellent

Milinda

Traveled with group, Business traveler, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in May 2025

10/10 Excellent

Kathy

Traveled with partner
Liked: Cleanliness, amenities
Awesome!
Stayed 4 nights in Apr 2025

8/10 Good

Steven

Liked: Cleanliness, staff & service, room comfort

Anniversary Trip 2025

The Southwinds Motel was a wonderful place to stay. I would highly recommend staying there for a nice couples retreat away. The service was wonderful and location perfect!
Stayed 4 nights in Apr 2025

10/10 Excellent

Donna, Lafayette

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Apr 2025

8/10 Good

Russell

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Friendly staff and loved having the Tipsy Rooster there. Enjoyed the music very much.
Stayed 5 nights in Apr 2025

10/10 Excellent

MICHAEL

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in May 2025

10/10 Excellent

Sara Irma

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
From the moment we checked in, meeting the front desk staff, they were friendly, gave us information to make our stay comfortable and worry free. Our room was towards the back, quiet, clean and parking right in front. We loved that parking is free. Another plus, besides a big coffee pot in the room, in the morning, grab and go continental breakfast in the lobby was very nice and convenient. Definitely would stay here again and I would recommend to other travelers.
Stayed 2 nights in Apr 2025