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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

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

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning
$191
includes taxes & fees
Nov 18 - Nov 19

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
(94 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
(68 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
(103 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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Property grounds
The Palms Hotel
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  • Breakfast included
  • Pet friendly
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4.4 out of 5, Excellent, 1,026 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.

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
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. 711 out of 1223 reviews
Rating 8 - Good. 317 out of 1223 reviews
Rating 6 - Okay. 127 out of 1223 reviews
Rating 4 - Poor. 50 out of 1223 reviews
Rating 2 - Terrible. 18 out of 1223 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

4/10 Poor

Alexandre

Liked: Staff & service
Bed bug on myself and my pregnant wife. :(
Stayed 1 night in Jul 2025

10/10 Excellent

George

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

Southwinds motel

The stay was excellent as the well as the location and the grounds. Staff was helpful as well .The value was a good
Stayed 4 nights in Jul 2025

4/10 Poor

Keith

Traveled with family
Disliked: Property conditions & facilities
We were asked when checking in if we used Orbitz, I said yes and she changed my room number. Room assignment was not what was shown on the website or in the photos.
Stayed 5 nights in Jul 2025

10/10 Excellent

Mike

Liked: Cleanliness, staff & service, property conditions & facilities
Was close to Duval st to walk. Bar on property was nice and once in the room really couldn't hear the outaide noise which was nice
Stayed 1 night in Aug 2025

10/10 Excellent

Cynthia

Stayed 2 nights in Aug 2025

10/10 Excellent

Verified traveler

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

several suggestions impovement

I would strongly advise installing safety bars in the shower as it is very slippery and I almost slipped and fell several times...nothing to hold on to. A better handle on the cockroach situation as well as we killed 4 of them in our room for a 5 day stay.
Stayed 5 nights in Jul 2025

10/10 Excellent

Anna

Liked: Cleanliness, staff & service, property conditions & facilities
This was a great place to stay especially for the price! Clean and comfortable. A bit of a walk to get to Mallory Square and the end of Duval, but we enjoyed the exercise. Plenty of places close by and the property has a bar. Ice machines weren’t really working so that was the only bummer. Staff was super friendly and helpful!
Stayed 2 nights in Jul 2025

4/10 Poor

rose marie

Traveled with family
Liked: Cleanliness
Disliked: Property conditions & facilities
Bathroom door does not lock, bathroom looks old, front door does not have a secure lock.
Stayed 1 night in Jul 2025

8/10 Good

Valery

Liked: Staff & service
Disliked: Property conditions & facilities
Really liked everything but the futon
Stayed 5 nights in Jul 2025

10/10 Excellent

Joanne

Stayed 3 nights in Jul 2025

6/10 Okay

Deborah

Traveled with partner
Liked: Cleanliness
The staff was fine, not particularly friendly. Parking was not good. The second pool was out of order, so the one pool was crowded.
Stayed 1 night in Jul 2025

4/10 Poor

PAM

Traveled with group
Disliked: Property conditions & facilities
Bathrooms extremely small and very old, no updates. Decorative Pillows on bed were dirty.
Stayed 2 nights in Jul 2025

10/10 Excellent

Keithia

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

8/10 Good

Michel

Stayed 1 night in Jul 2025

10/10 Excellent

Jayne

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

Had a great time as usual

The last 2 times we went this year. We traveled thru the night to get there by car. We live in South west Florida. They got us in the room right away! 9am! So grateful for the ladies in the office. So friendly
Stayed 3 nights in Jun 2025

10/10 Excellent

Frank

Liked: Cleanliness, staff & service, property conditions & facilities
The property was great and everyone was friendly and they had music, food right across the street and around the coner.
Stayed 4 nights in Jul 2025

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, property conditions & facilities
property is close to many of the restaurants that i frequent. Being a solo traveler I feel safe at this property
Stayed 5 nights in Jul 2025

8/10 Good

Varun

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Motel has been well maintained and the staff are very helpful. Location is great.
Stayed 1 night in Jul 2025

10/10 Excellent

Ashley

Liked: Cleanliness, staff & service, property conditions & facilities
While the property is older the rooms were clean and cold which was much appreciated. Staff was excellent and friendly. I was a little worried as the seal around the doors and the AC unit could stand to be addressed but no issues and the room served it's purpose. The TV is very small but who goes to Key West to watch TV? Overall I was pleasantly surprised and would stay at the motel again.
Stayed 2 nights in Jul 2025

10/10 Excellent

Autumn

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was perfect!
Stayed 4 nights in Jul 2025

10/10 Excellent

lisa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay right in the mix of everything to do!! Staff was great love smaller mom and pop places to stay
Stayed 3 nights in Jul 2025

4/10 Poor

Aneta

Disliked: Cleanliness, property conditions & facilities, room comfort

Disappointing Stay-Needs Serious Upgrades

I rarely leave negative reviews, but this hotel was truly below acceptable standards. The room was in dire need of upgrades — everything felt old, worn down, and poorly maintained. The floor was filthy when we arrived, and to make matters worse, the tub still had hair in it from a previous guest. That alone was enough to make me question the cleanliness of the entire room. The AC unit was not properly insulated, and during a thunderstorm, rainwater actually started leaking in through the unit. It was a huge mess and made us feel completely uncomfortable and unsafe. The pool was also a major letdown. It looked unkempt and murky, clearly not cleaned or properly maintained on a regular basis. We had looked forward to using it, but after seeing the condition, we decided it wasn’t worth the risk. Overall, I would not recommend staying here unless significant improvements are made. Cleanliness and basic maintenance should be a priority — unfortunately, this hotel failed on both fronts.
Bathroom tile
Walked from the bathroom to the bed barefoot.
Stayed 4 nights in Jul 2025

10/10 Excellent

Ronald

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location, location, location! Staff was friendly and attentive. Room was small but perfect as we werent really hanging in the room all day. Close to all Duval has to offer. We'll see you again Southwinds : )
Stayed 3 nights in Jul 2025

6/10 Okay

Gerald

Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service
Staff was unaccommodating at check-in to let us know what side of the property our room would be so we could carry our luggage to that part of the property
Stayed 1 night in Jul 2025

10/10 Excellent

TERESA

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved staying here. It may be an older motel, but it was clean, quiet, and offered plentiful breakfast options. The staff was incredibly friendly, and it was close to the high points of Key West. Additionally, it was close to the booth where you could sign up for the trolley or train to take you around Key West to explore the areas well known to KW that may not be within walking distance. We also appreciated that it had a liquor store and bar right next door, featuring live music every night at The Tipsy Rooster. If I ever return to Key West, I would definitely stay here again.
Stayed 2 nights in Jul 2025