Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Exterior
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated
Deluxe Room | Living area | 32-inch LED TV with cable channels, TV
2 outdoor pools, pool umbrellas, sun loungers
Deluxe Room | Terrace/patio

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Breakfast included
  • Bar
  • 24/7 front desk
  • Laundry
  • Pool
  • Air conditioning

Explore the area

Map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Key West Butterfly and Nature Conservatory
    ‪4 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

Standard Room, 1 King Bed

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

Deluxe Room

  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

Standard Room, 2 Queen Beds

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

Similar properties

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
  • Free crib
  • Highchair
  • 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

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. 608 out of 1065 reviews
Rating 8 - Good. 278 out of 1065 reviews
Rating 6 - Okay. 116 out of 1065 reviews
Rating 4 - Poor. 42 out of 1065 reviews
Rating 2 - Terrible. 21 out of 1065 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

Trevor

Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
Beware that there is a bar at the property with live music in the evening that goes til 1:30 a.m. This bar was right beside my window. I was told at checkin that the music only went til 11 p.m., which I didn't think was unreasonable. However when it was still going strong at 12:30, I called reception and was told, "No, it doesn't end til 1:30 a.m." I find it hard to believe that they didn't know that when I checked in. At first the manager was not willing to allow me to cancel my second night and get a refund. It was only after I got Expedia involved (thanks to the helpful folks at Expedia) that he was willing to do so. He remainded unwilling to discount my first night. So I paid $350 CAD for 3 1/2 hours sleep. He assured me that he would let all staff know how late the music actually goes, so if you are told otherwise, let my lesson be your guide. Otherwise the property is fine and the bed was comfortable. It will work if you don't mind live music literally outside your room (Room 19) til 1:30 a.m.
Stayed 2 nights in Nov 2024

6/10 Okay

Steve

Traveled with group
Stayed 3 nights in Nov 2024

10/10 Excellent

Michelle

Liked: Cleanliness, staff & service, property conditions & facilities
Great location. Friendly helpful staff. Room clean.
Stayed 3 nights in Nov 2024

8/10 Good

Theresa

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Nov 2024

8/10 Good

Janet

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Nov 2024

6/10 Okay

Christopher, Fort Myers

Liked: Staff & service
Stayed 3 nights in Nov 2024

8/10 Good

Walter

Stayed 4 nights in Oct 2024

10/10 Excellent

james

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
First time for us visiting the Southwinds and we thought it was a great location. We had a daily stop at the Tipsy Rooster, which is located on the property, to relax while listening to the live music.
Stayed 7 nights in Nov 2024

10/10 Excellent

terry

Stayed 3 nights in Oct 2024

8/10 Good

Laura

Liked: Cleanliness, staff & service, property conditions & facilities
Cute room close to Duval Street. Would stay again
Stayed 2 nights in Nov 2024

10/10 Excellent

Tessa, Land O Lakes

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff and location is great!
Stayed 2 nights in Aug 2024

8/10 Good

Jennifer

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
We loved it!
We really enjoyed our stay at Southwinds Motel! We loved the location of it. The staff was so friendly. We would definitely stay there again!! My sister and I surprised our dad for his birthday with a little quick trip to KW!
Stayed 2 nights in Nov 2024

8/10 Good

Tara

Liked: Cleanliness, staff & service
Stayed 5 nights in Nov 2024

10/10 Excellent

Darlyne

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Minutes prom Duval St. in an affordable, clean, friendly and small establishment. Stayed on a Sunday night; surprised to hear VERY LOUD music until after midnight. Still worth it!
Stayed 1 night in Nov 2024

10/10 Excellent

Susan Diana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The check-in process was very easy management was excellent to work with they gave me many tips on places to go and things to do. Thank you Carlos

10/10 Excellent

Joseph

Liked: Cleanliness, staff & service
Very helpful staff. Carlos was great to work with, giving good locals advice. The location is perfect for beach access and Duvall access. Have already booked my next trip
Stayed 2 nights in Oct 2024

8/10 Good

DPL

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is not new. Staff is helpful and they have an outdoor bar with live music every nite. And food is available in the area and all over town. And lots of bars. Walk to Southernmost marker and Hemingway House. Near south end of Duval St. Long walk to seaport. Desk told us about public transport, great!! And they can book some activities if available. JET SKI around Key West!!!! Watch the weather. Lots of waves during Rapheal! We had a good 4 days.
Stayed 3 nights in Nov 2024

10/10 Excellent

Sally

Liked: Cleanliness, staff & service, property conditions & facilities
Nice location
Stayed 3 nights in Nov 2024

10/10 Excellent

LISA MARIE, Greensboro

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay
Stayed 4 nights in Oct 2024

8/10 Good

Stacy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great rate for Key West. Bar on property. We actually had the room attached to the bar. We sleep with a sound machine & didn't hear a thing. Pool had lots of leaves in the filter. Room was basic, but you don't need much more in Key West. Bed very comfortable.
Stayed 1 night in Oct 2024

6/10 Okay

Sherree, Lady lake

Traveled with group, Traveled with partner
Disliked: Amenities, property conditions & facilities
Was a confusing checkin. Only did room service every 3 days but that was not explained so used and hung towels, went and grabbed pool towels to use. Carried out own garbage to the dumpster and had a one use shampoo bottle to use for the two of use for 3 days.When you pay almost $300 a night and resort fee .... You do not even get room cleaned or towels. C'mon be better than this! We loved Key West and Carlos (employee) was amazing!!! Also gave me some shampoo/clean towels on day 4...
Stayed 3 nights in Nov 2024

10/10 Excellent

denise

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy to walk around and two pools were great!
Stayed 4 nights in Oct 2024

10/10 Excellent

Denise

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone and everything was fabulous.
Stayed 3 nights in Oct 2024

10/10 Excellent

Darren

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in Oct 2024

2/10 Terrible

John

Traveled with partner
Disliked: Amenities, property conditions & facilities
My plans had changed and one month before the 10/24 reservation, I submitted a request for a cancellation with full refund to Expedia. You rejected the request. I emailed the manager Umberto, explaining that you could easily resell the room since it was a month before and this was Fantasy Fest. He refused. So if a I cancelled with no returned you could resell the room and get paid for it twice. This is just wrong. He still refused. The room did not look anything like the room in the ad. The tiles in the bathroom were moving and about to fall through. The pressure in the shower was very low.
Stayed 3 nights in Oct 2024