See all properties

Southwinds Motel

2.0 star property

Choose dates to view prices

your current months are January, 2025 and February, 2025.
January 2025
February 2025

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
Deluxe Room | Terrace/patio
2 outdoor pools, pool umbrellas, sun loungers

Reviews

8.8 out of 10

Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • 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

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

  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

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

  • 400 sq ft
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

  • 250 sq ft
  • Sleeps 3
  • 1 Queen Bed

Similar properties

Interior entrance

Wicker Guesthouse

Pool
Breakfast included
Pet friendly
Parking included
4.3 out of 5, Excellent, (1000)
The price is $479
per night
$539 total
includes taxes & fees
Jan 14 - Jan 15
Wicker Guesthouse

About the neighborhood

Key West

Located in Key West (Key West Historic District), Southwinds Motel is within a 5-minute walk of Duval Street and South Beach. .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
  • South Beach - 3 min walk
  • Southernmost Point - 4 min walk
  • Ernest Hemingway Home and Museum - 11 min walk
  • Mallory Square - 4 min drive

Getting around

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

Restaurants

  • ‪El Siboney Restaurant - ‬8 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Southernmost Point Bar In the USA - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach
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.
Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities, which include bicycles to rent. Additional features at this hotel include concierge services, a picnic area, and a vending machine.
Quench your thirst with your favorite 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. Limited parking 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.

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

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. 596 out of 1047 reviews" "
Rating 8 - Good. 271 out of 1047 reviews" "
Rating 6 - Okay. 116 out of 1047 reviews" "
Rating 4 - Poor. 42 out of 1047 reviews" "
Rating 2 - Terrible. 22 out of 1047 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

10/10 Excellent

Tracy, Miami

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Sep 2024

8/10 Good

Theresa Ann

Traveled with group, Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was very helpful, The room we had was a little small, It has 2 queen beds - would have been better if we had more space ( 3 women). The room needed another mirror - only 1 in the bathroom. Clean, felt safe The location was great. I like the Tipsy rooster bar and package store. Beach is close by.
Stayed 4 nights in Sep 2024

10/10 Excellent

Alanna

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great little spot off the beaten path
Stayed 2 nights in Aug 2024

4/10 Poor

Troy

Traveled with partner
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service
The rooms are clean. That being said, they only clean your room every third day. Supposedly new towels and sheets. Our wash cloths never left where we left them. Our sheets were never changed. They just remade our bed. I know that because our fitted sheet had a small hole in it. That same hole was still there after they remade our bed. It was great for the price but I wouldn’t go back given the other options.
Stayed 5 nights in Sep 2024

10/10 Excellent

michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 1 night in Sep 2024

10/10 Excellent

Rafael

Liked: Cleanliness, staff & service, property conditions & facilities
Excellent to stay
Stayed 2 nights in Sep 2024

10/10 Excellent

Mary

Traveled with family
Liked: Staff & service, property conditions & facilities
Pool right outside our room
Stayed 2 nights in Sep 2024

8/10 Good

Marilyn

Liked: Cleanliness, staff & service
Stayed 3 nights in Sep 2024

6/10 Okay

Janet

Traveled with group
Disliked: Cleanliness, amenities
This was my 4th time staying at Southwinds and probably my last. The motel's policy to clean rooms every 3rd day is a bad one. We had garbage overflowing and a pile of wet dirty towels on the bathroom floor. During our week long stay, our room was cleaned once.
Stayed 6 nights in Sep 2024

8/10 Good

Paul

Stayed 3 nights in Sep 2024

10/10 Excellent

Rodney

Stayed 2 nights in Sep 2024

10/10 Excellent

DEAN

Stayed 7 nights in Aug 2024

10/10 Excellent

renee

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
absolutely in love with this place!!!!
Stayed 5 nights in Sep 2024

10/10 Excellent

JOHN, Brooklyn

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff here do all they can to satisfy a request. They are happy and helpful. Close to beaches and rentals. Some minor touch ups around facilities would be helpful. The Tipsy Rooster is outstanding. This was our 2nd stay here and we will stay again.
Stayed 4 nights in Sep 2024

8/10 Good

Darlene

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

8/10 Good

Ken

Liked: Amenities
Great location very reasonably priced
Stayed 1 night in Sep 2024

10/10 Excellent

Kimberly

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Sep 2024

4/10 Poor

Julie

Stayed 1 night in Sep 2024

6/10 Okay

Darrell

Disliked: Cleanliness, amenities, property conditions & facilities
The people were very nice, but bugs in the room and pool dirty, breakfast was good. Location is grea5
Stayed 1 night in Sep 2024

10/10 Excellent

Melissa

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Favorite place in I stay
Stayed 7 nights in Sep 2024

10/10 Excellent

Jenna

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
I really loved the old Key West charm and convenient location. There is a bar onsite! And an ice cream stand. The continental breakfast was pretty impressive too! I would stay here again.
Stayed 2 nights in Jun 2024

10/10 Excellent

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff who were able to get me into a room almost 3 hours earlier than the check-in time. Small room but clean and a very comfortable bed. Provided a free simple breakfast- coffee, muffins, bananas, yogurt, and cereal. The Tipsy Rooster attached to the motel is a great place to hang out for some drinks and local music artists. Spent a few hours in the clean/clear pool. Walkable to Duval Street. I highly recommend and would stay here again. Zero issues/complaints.
Stayed 5 nights in Sep 2024

10/10 Excellent

Debra

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great stay - small room
This was a great little motel, just one street over from Duval Street ( which is the Main Street in Key West). It was a small room, but just perfect for us just to sleep in. We spent most of our time exploring Key West. Found out from one of the tours that this was the first motel in Key West. But they have kept it up well.
Stayed 2 nights in Sep 2024

8/10 Good

Ellen

Traveled with partner
Liked: Amenities
Loved the location of the Motel, and the breakfasts were good, but felt our furniture could have been repaired. i.e. the drawers were falling out of the dresser a d the nightstand was not in good repair, nor the table.
Stayed 7 nights in Sep 2024

10/10 Excellent

Verified traveler

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 1 night in Sep 2024