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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Property grounds
Reception
Front of property

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar
$447
includes taxes & fees
Feb 1 - Feb 2

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
(100 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
(107 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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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)

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. 736 out of 1281 reviews
Rating 8 - Good. 334 out of 1281 reviews
Rating 6 - Okay. 137 out of 1281 reviews
Rating 4 - Poor. 53 out of 1281 reviews
Rating 2 - Terrible. 21 out of 1281 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

10/10 Excellent

Kevin

Liked: Cleanliness, staff & service, amenities
Nightly entertainment at the tipsy rooster was a huge treat! Check in was fast and easy! Clean cool room. Great location to the beach!
Stayed 3 nights in Oct 2025

10/10 Excellent

Alan

Stayed 2 nights in Sep 2025

10/10 Excellent

Michael

Liked: Cleanliness, amenities, property conditions & facilities
grerat room at a great price
Stayed 1 night in Oct 2025

10/10 Excellent

Cristy

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A true hidden gem in Old Town - very clean, comfortable rooms, staff was wonderful!
Stayed 5 nights in Oct 2025

8/10 Good

Crystal

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We loved our stay here. The room was clean, the staff very friendly and helpful. We loved the bar out front and the live music. And the close proximity to the beach. The pool was nice. Great location to everything we walked alot and also took an uber. Would have liked another luggage stand or somewhere for our clothes but, we knew coming that the room didn't come with dressers or a closet. We will definitely come stay here again.
Stayed 6 nights in Oct 2025

10/10 Excellent

Raquel

Traveled with partner
Liked: Staff & service, amenities, property conditions & facilities
I loved that you could get a daily pass to the beach for towels and chairs, they had laundry(free of charge) onsite that included the soap.
Stayed 6 nights in Oct 2025

10/10 Excellent

Liena

Liked: Cleanliness, staff & service, property conditions & facilities
It was a good stance, we reserved 3 rooms and were clean (as clean as possible)and the staff hepful. We recomend this motel if you plan a gateway based in to know the town since is not the updated place, however it was a nice sorprais, we would stay there again if come back to key kest.!!
Stayed 1 night in Oct 2025

10/10 Excellent

Catherine

Traveled with family
Liked: Cleanliness, staff & service, amenities
Location, location, location! The place looked questionable from the outside, but the service was great and the room was great!
Stayed 2 nights in May 2025

6/10 Okay

Barry

Liked: Cleanliness
Disliked: Staff & service
Tiny rooms. Tiny TV. The bathroom is so small you can’t even close the door while sitting on the toilet. The breakfast was just a counter with some packaged muffins, yogurt packs, packaged eggs.
Stayed 3 nights in Oct 2025

8/10 Good

Bonnie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
There was an issue with the location and facilities of the room but they were resolved with no extra effort
Stayed 4 nights in Oct 2025

8/10 Good

Nancy, Winfield

Traveled with partner
Good location and comfortable enough for the price. We did not realize there is a $25 daily resort fee so be aware. Not sure what for as bike rentals are extra. Guess maybe just for use of the pools?
Stayed 6 nights in Oct 2025

10/10 Excellent

David

Traveled with partner
We loved the island vibe of this older establishment. Everyone on the staff was pleasant, helpful, and great! On the Duval bus loop, but the entire area is an easy walk away. We had the pool to ourselves over half the time. Thank you!
Stayed 6 nights in Oct 2025

10/10 Excellent

Susan

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I stayed 2 nights on the property. Room was large and clean. The bathroom was small but clean. Pool was great after walking around all day. Parking was a little tight but we were so close to Duval St., we never used our car while on the island. We did rent scooters for the day which I would highly recommend to explore more of the island. Hotel does rent bikes and scooters as well.
Stayed 2 nights in Oct 2025

8/10 Good

Joanna

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Oct 2025

10/10 Excellent

Renee

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was great! Friendly, helpful and doing what they could to make our stay even better.
Stayed 4 nights in Oct 2025

8/10 Good

ROBIN

Liked: Cleanliness, staff & service, property conditions & facilities
Property was safe no issues. Room was clean and comfortable.
Stayed 3 nights in Oct 2025

8/10 Good

Don

Stayed 7 nights in Oct 2025

10/10 Excellent

Perry

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

Location. Location. Location!

Perfect location for everything in Key West.
Stayed 2 nights in Oct 2025

10/10 Excellent

Kathy

Traveled with partner
Liked: Amenities
Very safe
Stayed 3 nights in Oct 2025

8/10 Good

Marlene

Liked: Cleanliness, staff & service, room comfort
Pool area was ok, nothing special
Stayed 4 nights in Oct 2025

10/10 Excellent

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great place!! Centrally located to be able to walk all over and check out the Duval Street area. Suited our needs perfectly.
Stayed 3 nights in Oct 2025

8/10 Good

Eileen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Bathroom was extremely small, a little outdated. But was clean and quiet! Staff was friendly!
Stayed 2 nights in Oct 2025

10/10 Excellent

Jennie

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great little motel, staff is great & clean rooms. The bar next door is so convenient
Stayed 6 nights in Oct 2025

8/10 Good

SUSAN, Pella

Traveled with family
Disliked: Property conditions & facilities
Pool area was very small and dated.
Stayed 1 night in Oct 2025

10/10 Excellent

Terry

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
We had an amazing 5 night stay. Tipsy Rooster bar is awesome as well.
Stayed 5 nights in Oct 2025