Southwinds Motel

Property class: 2

Choose dates to view prices

Located close to South Beach and Southernmost Point, Southwinds Motel provides free continental breakfast, laundry facilities, and an outdoor entertainment area. Guests can also expect to find a bar.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Parking available
  • Bar

Room options

Available filters for rooms
Showing 4 of 4 rooms

View all photos for Standard Room, 1 Queen Bed

A hotel room with a bed, a wardrobe, a door, a microwave, and a bathroom with a toilet and towel rack.

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(117 reviews)
  • 250 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

A hotel room with two beds, a TV, and a window with blinds.

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(95 reviews)
  • 400 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

A hotel room with a bed, a bedside table with a lamp, a coffee maker, and a window with blinds.

Deluxe Room

10.0 out of 10
Exceptional
(8 reviews)
  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

A hotel room with a large bed, a TV mounted on the wall, a small table with chairs, and a window with curtains.

Standard Room, 1 King Bed

8.4 out of 10
Very good
(135 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Located near the beach, Southwinds Motel is in Old Town Key West, a neighborhood in Key West. Duval Street and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at South Beach and Clarence S. Higgs Memorial Beach Park. Ernest Hemingway Home and Museum and Mallory Square are two other places to visit that come recommended. Discover the area's water adventures with kayaking, scuba diving, and snorkeling nearby, or enjoy the great outdoors with ecotours. Visit our Key West travel guide
Map
1321 Simonton Street, Key West, FL, 33040

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    3 min walk - 0.2 miles
  • A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.
    South Beach
    3 min walk - 0.2 miles
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    5 min walk - 0.3 miles
  • A beach sign with rules and hours for Clarence S. Hughes Memorial Beach.
    Clarence S. Higgs Memorial Beach Park
    9 min walk - 0.5 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    9 min walk - 0.5 miles

Getting around

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

Restaurants

  • Circle K
    6 min walk
  • Cuban Coffee Queen (Duval)
    5 min walk
  • Southernmost Point Bar in the USA
    5 min walk
  • Southernmost Beach Café
    3 min walk
  • Banana Cafe
    4 min walk

About this property

Southwinds Motel

  • Hotel near Duval Street
  • Located close to South Beach and Southernmost Point, Southwinds Motel provides free continental breakfast, laundry facilities, and an outdoor entertainment area. Guests can also expect to find a bar.
  • You'll also enjoy the following perks during your stay:
    • 2 outdoor pools along with sun loungers and pool umbrellas
    • Self parking (surcharge), luggage storage, and free newspapers
    • Multilingual staff, a 24-hour front desk, and outdoor furniture
    • A vending machine, tour/ticket assistance, and concierge services
    • Guest reviews give top marks for the beach locale and helpful staff
  • Room features
  • All 58 individually furnished rooms include comforts such as premium bedding and air conditioning. Guest reviews highly rate the clean rooms at the property.
  • Other amenities include:
    • Highchairs and free infant beds
    • Pillowtop mattresses and down comforters
    • Bathrooms with showers and free toiletries
    • 32-inch LED TVs with cable channels
    • Refrigerators, microwaves, and coffee/tea makers

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Frequently asked questions

Does Southwinds Motel have a pool?

Yes, this property has 2 outdoor pools.

How much does it cost to stay at Southwinds Motel?

As of Oct 24, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Oct 26, 2026 start from $190, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Southwinds Motel pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is available for USD 22.50 per day.

What time is check-in at Southwinds Motel?

Check-in start time: 4:00 PM; Check-in end time: midnight. Late check-in is available during limited hours.

What time is check-out at Southwinds Motel?

Check-out is at 11 AM.

Where is Southwinds Motel located?

Located in Old Town Key West, this hotel is within a 5-minute walk of Duval Street, South Beach, and Southernmost Point. Ernest Hemingway Home and Museum and Clarence S. Higgs Memorial Beach Park are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Southwinds Motel Reviews

8.6

Excellent

8.8

Cleanliness

8.4

Amenities

9.0

Staff & service

8.2

Property conditions & facilities
Rating 10 - Excellent. 760 out of 1395 reviews
Rating 8 - Good. 376 out of 1395 reviews
Rating 6 - Okay. 167 out of 1395 reviews
Rating 4 - Poor. 59 out of 1395 reviews
Rating 2 - Terrible. 33 out of 1395 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and the staff was very helpful
Stayed 4 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We have stayed at this facility for the last two years now and have been very pleased with the staff, the grounds, and the condition of the rooms. We will be booking with them again next year.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property and the staff very helpful and friendly.
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was very professional.
Stayed 1 night in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Tipsey Rooster out front is an EXCELLENT little outdoor bar....GREAT Music daily! Daytime Front Desk Ladies are Super sweet. Muffins are Amazing!
Stayed 7 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very helpful, clean room, has a great time.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Close to a lot of places I wanted to see. The ice cream and doughnuts bar was awesome! The was really comfortable.
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent stay. Beds en room were very comfortable. Breakfast was great every morning. Very friendly staff.
Stayed 6 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room, nice pool, nice staff. Good little Cuban restaurant and grocery store across the street. Loved it.
Stayed 4 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities
Enjoyed the stay, still a great location, experience, and value.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice for the price point. Very friendly and helpful staff
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly staff, clean rooms and property with an old school feel. We enjoyed our stay and will return.
Stayed 1 night in Aug 2026
Verified review

4/10 Poor

I always enjoy staying at South Winds. They treat you good, I hate to see the historic motel demolished in next few years, that of KW will not be the same. 4 **** stars
Stayed 5 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent staff and a fun place to stay.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Mom and Pop type property. Perfect location. Store across the street for food and drinks. Bar with daily music right next door. One block away from Duval street with many restaurants and bars. You go to South Florida for the weather. Have to say it was the hottest and most humid place I have ever been to for a solid week! Pool was great and definitely needed. Would stay there again in a heartbeat.
Stayed 7 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities
Room was clean and the staff was very helpful. Location of motel was very convenient to get to Duval street
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was small and old fashioned, but it had an old Florida vibe that we loved. Everything we needed was there. The staff were very helpful.
Stayed 2 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location.
Stayed 4 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Place was ok, Bar on premise and they had music, my room had ants(I told em and came and sprayed), pool was clean, the roosters were cool, They want 22.50 a day to park, waived it I'm handicap
Stayed 2 nights in Sep 2026
Verified review

8/10 Good

Good location and price.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good food
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
SOUTHWINDS MOTEL WAS AN ABSOLUTELY PERFECT TO STAY IN KW!!!! The amenities were perfect, the moring breakfast was just perfect, and thee LOCATION IS SUPER GREAT. Literally minutes from everywhere. WE WILL BE BACK, FOR SURE!!!!!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our room was huge w 2 Queen size beds. Nice having fridge and microwave in room. The pool was right out side our door. The Zombie Bike Parade went right by our hotel - perfect viewing location. Close to Southernmost Point. Plenty of parking. Staff were quick to assist when a table umbrella blew over w the wind (cameras monitor the pool area). Hammocks were a nice option for relaxing. Water pressure was the only bad thing but according to “pool talk” it depended on where your room was located. We would definitely stay here again.
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Dated but very cute! Beds were comfy and linens smelled very clean. Unfortunately no hot water made showering chilly. Pool was clean warm and very nice!
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great helpful staff. Locations was good, not busy but walkable to busy areas .
Stayed 1 night in Jul 2026