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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

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

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar
$284
$252 nightly
$284 total
Total with taxes and fees
May 10 - May 11

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.)
    ‪11 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
(107 reviews)
  • 250 sq ft
  • 1 bedroom
  • 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
(79 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
(112 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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About the neighborhood

Key West

With a stay at Southwinds Motel in Key West (Old Town Key West), you'll be steps from South Beach and 3 minutes by foot from Duval Street. .This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.

What's nearby

  • Duval Street - 3 min walk - 0.2 miles
  • South Beach - 3 min walk - 0.2 miles
  • Southernmost Point - 5 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 8 min drive

Restaurants

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 min walk

About this property

Southwinds Motel

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.

Make yourself at home in one of the 58 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with down comforters and premium bedding. 32-inch LED televisions are provided, with cable programming available. Private bathrooms with showers feature complimentary toiletries and hair dryers.
Make use of convenient amenities such as concierge services, a picnic area, and a vending machine.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:00 AM to 10:00 AM.
Featured amenities include complimentary newspapers in the lobby, a 24-hour front desk, and multilingual staff. Self parking (subject to charges) is available onsite.
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

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

8.6

Excellent

Rating 10 - Excellent. 732 out of 1315 reviews
Rating 8 - Good. 351 out of 1315 reviews
Rating 6 - Okay. 147 out of 1315 reviews
Rating 4 - Poor. 58 out of 1315 reviews
Rating 2 - Terrible. 27 out of 1315 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

6/10 Okay

Robert

Traveled with partner
Liked: Cleanliness
Disliked: Amenities, property conditions & facilities
Room was ok, small but clean. Location was good, easy access to the beach, Duval, about a 35 min walk to the west side and port. Used to be free parking but now are charging. Not sure what the resort fee paid for outside of the pool. Downside. Staff was not friendly or helpful. Acted as if we were inconveniencing them the entire week we were there. Complimentary breakfast was pretty weak. No hot water on our last day/night. Pretty loud each evening with the band in the bar anywhere from 6pm to past 10 depending on the evening - felt like they were in our room on a couple of nights. First trip to Key West and our stay here was disappointing. Would not come back to this facility.
Stayed 7 nights in Jan 2026

10/10 Excellent

Lucy

Traveled with partner
Liked: Amenities
Everyone was nice and courteous. Quiet place. Really enjoyed our weekend
Stayed 3 nights in Jan 2026

8/10 Good

Susie

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very clean. Great location. Small rooms. WiFi did not work very well in our room (#5). But we would stay here again.
Stayed 3 nights in Jan 2026

8/10 Good

Frederick

Traveled with partner
Liked: Cleanliness, staff & service, amenities
Very low water pressure. Showing it's age
Stayed 2 nights in Jan 2026

4/10 Poor

Robin

Stayed 1 night in Jan 2026

8/10 Good

Tom

Traveled with pets, Traveled with family
Liked: Cleanliness, property conditions & facilities
The room was nice, clean and comfortable. It was a bit small as we travel with our little dogs, however it had a great bed. The faucet and shower controls should be replaced as it was very difficult to adjust the temperature on both. The staff was great and the breakfast was the best. Value was worth the price.
Stayed 3 nights in Jan 2026

10/10 Excellent

James

Liked: Amenities
Old Needs updating Great location Friendly staff
Stayed 4 nights in Jan 2026

6/10 Okay

steve

Stayed 2 nights in Jan 2026

8/10 Good

john

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location was great, close to 2 beaches. Property was nice and clean. Rooms were small but fine. Was there 4 days and basically had bad oranges and no other fruit for the time spent. Had plenty of bagged muffins, yogurt, and cereals. One beaches supplier you with towels and chair you just have to get a pass from the front desk. Great outside live music every night. Would definitely stay again.
Stayed 4 nights in Jan 2026

6/10 Okay

Tatiana

Traveled with family
Liked: Cleanliness, amenities
Disliked: Property conditions & facilities
Guys for the price this is pretty run down property even though the rooms were clean. The breakfast served was really a junk. I understand that I decided to stay in a MOTEL but still, even cheap food can be better quality. The staff was courteous and professional and friendly. Really, just staff and room cleanliness were positives of this place.
Stayed 4 nights in Jan 2026

10/10 Excellent

MATTHEW

Liked: Cleanliness, staff & service, amenities
Staff was wonderful, pleasantly surprised that we got free towels and chairs at beach.
Stayed 7 nights in Dec 2025

10/10 Excellent

Heather

Traveled with family
Liked: Cleanliness, staff & service, amenities
Everyone enjoyed it. The warm pool was very nice. The location was wonderful.
Stayed 3 nights in Jan 2026

6/10 Okay

Michael

Liked: Staff & service
Stayed 2 nights in Jan 2026

10/10 Excellent

Yohei

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Check-in staff was kind and friendly. We arrived at the hotel earlier and they accommodated an early check in as there was a room ready.
Stayed 1 night in Dec 2025

6/10 Okay

Boguslawa

Traveled with family
Liked: Cleanliness, staff & service, amenities
Was ok,nothing special
Stayed 1 night in Jan 2026

2/10 Terrible

Duane

Traveled with family
Liked: Cleanliness
Disliked: Amenities
Walls are paper thin, the ac unit didn’t work, and there was a 30 dollar charge for a resort fee and a 20 dollar parking fee on top of the price you pay on hotels.com.
Stayed 1 night in Jan 2026

8/10 Good

Danny

Liked: Cleanliness, room comfort
Great location !! Close to southern most point
Stayed 2 nights in Nov 2025

10/10 Excellent

Steve, Trevor

Liked: Cleanliness, amenities, property conditions & facilities
Everything was great. From staff to service.
Stayed 4 nights in Oct 2025

8/10 Good

John clark

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
The bar next to our room was very loud!!!!
Stayed 1 night in Dec 2025

6/10 Okay

Carrie

Traveled with family
Liked: Cleanliness, staff & service
Disliked: Amenities
For the amount paid it’s a small room with no parking. And the continental breakfast was minimal
Stayed 3 nights in Dec 2025

8/10 Good

jessica Leigh

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast is a quick stop and go. Met expectations and was appreciated. Room and property is so clean a quaint. I really enjoyed all of the amenities and location. Ended up in that heated pool everyday. So nice! Will be back.
Stayed 2 nights in Dec 2025

10/10 Excellent

Anuradha

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Excellent Location, Excellent Staff, Great rates. Breakfast Included. This motel is within walking distance to Southernmost point, Duvall Street, Ft Zachary Taylor Park and many other locations.
Stayed 2 nights in Dec 2025

10/10 Excellent

Heather

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room. Great location. Friendly staff
Stayed 1 night in Dec 2025

8/10 Good

Collette

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect location. Affordable. Clean. Friendly staff.
Stayed 4 nights in Dec 2025

10/10 Excellent

Mary

Stayed 3 nights in Dec 2025