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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Exterior
Standard Room, 2 Queen Beds | 1 bedroom, premium bedding, down comforters, pillowtop beds
Exterior
2 outdoor pools, pool umbrellas, sun loungers
Deluxe Room | Living area | 32-inch LED TV with cable channels, TV

Reviews

8.8 out of 10
Excellent

Popular amenities

  • 24/7 front desk
  • Bar
  • 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
    ‪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

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Deluxe Room | Living area | 32-inch LED TV with cable channels, TV

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 | 1 bedroom, premium bedding, down comforters, pillowtop beds

Standard Room, 2 Queen Beds

  • 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

  • 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, (1002)
$239 nightly
The price was $253
The price is $239 total
includes taxes & fees
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. 634 out of 1104 reviews
Rating 8 - Good. 288 out of 1104 reviews
Rating 6 - Okay. 121 out of 1104 reviews
Rating 4 - Poor. 43 out of 1104 reviews
Rating 2 - Terrible. 18 out of 1104 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

ronald

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location
Stayed 4 nights in Mar 2025

6/10 Okay

Veronica

Traveled with family

Perfect for the night

I book three rooms for a group of 2 adults with 6 teenagers. Its not a fancy place but certainly a comfortable one. Its close to everything just 20 min walk from the boat docks. Live music and entertainment, bar, snack mobile, Hammocks, scooter rentals all you can possibly needs for a short fun stay. Just 2 blocks from the famous Key West buoy. Front desk service was kind and efficient. Will stay here again.
Stayed 1 night in Mar 2025

10/10 Excellent

Doug

Stayed 2 nights in Mar 2025

10/10 Excellent

Bruce

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love staying here!!! The staff is always amazing and the rooms are nice and clean. Parking outside your room is a bonus. Convenient walk to beaches, bars and dining.
Stayed 1 night in Mar 2025

6/10 Okay

Nikhil

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Nov 2024

10/10 Excellent

Kerry

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I am a repeat customer and will come back again!
Stayed 2 nights in Mar 2025

8/10 Good

Marilyn

Stayed 3 nights in Mar 2025

6/10 Okay

Karen

Liked: Staff & service, property conditions & facilities
Stayed 3 nights in Mar 2025

10/10 Excellent

Jason

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Mar 2025

8/10 Good

Linda

Liked: Cleanliness, staff & service, room comfort

Up and down

The check in process was easy. The property offers 2 pools,( 1 smaller heated one) which are clean, and a very basic continental breakfast with several comfortable outdoor areas. Unfortunately, maid service is only every 3 days, but we had to specifically ask for our room to be done because our room was not initally on the list for our 3rd day there. The room, itself, is clean, but is a very, very dated room with a tiny bathroom, though the bed is comfortable. The location is great and musical entertainment is offered daily as part of the complex, along with outdoor bar and pricy ice cream truck. The Cuban restaurant across the street is casual and delicious. The staff are very helpful and friendly.
Stayed 4 nights in Mar 2025

4/10 Poor

Patricia

Disliked: Property conditions & facilities
The property just needed maintenance. Bushes and landscaping needed attention. Seals around the door needed attention. General maintenance.
Stayed 2 nights in Mar 2025

10/10 Excellent

Jennifer

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities
This was my 3rd time in Key West and the first time at Southwinds with my lifelong best friend of almost 50 years. Couldn’t have asked for better service, accommodations, location, comfort and all-around amazing! I highly recommend Southwinds. Definitely will return!
Stayed 4 nights in Feb 2025

10/10 Excellent

Pennie, Greensboro

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the location of this property. Just blocks away from Duval St and the beach.
Stayed 3 nights in Feb 2025

10/10 Excellent

William

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Mar 2025

10/10 Excellent

David

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

8/10 Good

Martin

Traveled with partner
Disliked: Amenities
Whole property could use a paint job but beds we’re comfortable and shower was good. Heated pool was nice
Stayed 3 nights in Feb 2025

8/10 Good

Ramona

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful motel, well maintained. Staff was friendly.
Stayed 3 nights in Feb 2025

10/10 Excellent

Daniel

Liked: Staff & service
No frills vacation. Was what we wanted for a 4 night get away.
Stayed 4 nights in Feb 2025

10/10 Excellent

Adele

Stayed 2 nights in Feb 2025

10/10 Excellent

Kevin

Stayed 1 night in Feb 2025

10/10 Excellent

Anita

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very convenient place and rooms very clean and inviting. Nice to have a bar attached. I would ensure room you get in not near nightclub next door if you want an early night.
Stayed 1 night in Feb 2025

8/10 Good

Judy, Apex

Traveled with partner, Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
We liked the music each day on the property and the sitting area in front of the office. We could sit and talk without being directly in front of the music/Bar area. The breakfast was basic, not much for non-carb eaters. Also, unfortunately, only had non-dairy creamers which are full of chemicals. There is milk available, just hated opening a whole carton for a small amount. Towels were soft and thick. One bed was comfortable, the other squeaked and was worn. Bathroom sink was very small, hard to wash your face and no where to set toiletries. No shelf at all in shower, have to place soap and shampoo on the floor. Very hard for a senior person and just plain annoying. Over all a good motel, a little pricey but similar to others in area. We recommend staying here if you don't mind the small annoyances.
Stayed 4 nights in Feb 2025

8/10 Good

Mary

Traveled with family
Liked: Cleanliness, staff & service, amenities
The location was perfect close to the ocean and Duval Street. The motel has character and is tastefully arranged on the outside. The front seating area and live music was wonderful. It was nice to be able to rent bicycles right at the mote. The staff was wonderful. For the price - the room could have been in a little better shape. It was very small, and the towel racks were falling off the wall.
Stayed 4 nights in Feb 2025

10/10 Excellent

chester

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

Great location with great staff.

Check in was quick and painless. Staff was friendly and helpful. Rooms are clean and comfortable. Thanks for the hospitality. Location is perfect, 2 blocks from southern most point and 1 mile to sloppy Joe’s. Never had to drive anywhere.
Stayed 2 nights in Feb 2025

8/10 Good

Verified traveler

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

Decent place with good location

Good location about 15 minute walk to busy Duval bars. Close to Southermost point. Bed comfortable, not many drawers, had to live out of our bags. Nice having a bar in front of hotel.
Stayed 3 nights in Feb 2025