Southwinds Motel

See all properties

Choose dates to view prices

Dates

January 2025

February 2025

2 outdoor pools, pool umbrellas, pool loungers

Overview
Rooms
Location
Policies

Excellent

Popular amenities

Breakfast included

24/7 front desk

Bar

Laundry

Pool

Air conditioning

Explore the area

1321 Simonton Street, Key West, FL, 33040

Duval Street
3 min walk
South Beach
3 min walk
Ana's Cuban Cafe
1 min walk
Key West, FL (EYW-Key West Intl.)
8 min drive

Room options

Standard Room, 1 King Bed

28 sq m
Sleeps 3
1 King Bed

Premium bedding, down duvets, pillow-top beds, individually decorated

Deluxe Room

28 sq m
Sleeps 4
1 Queen Bed and 1 Double Sofa Bed

Standard Room, 2 Queen Beds

37 sq m
Sleeps 4
2 Queen Beds

Standard Room, 1 Queen Bed

23 sq m
Sleeps 3
1 Queen Bed

Similar properties

Pool

Breakfast included

Pet-friendly

Parking included

for 1 night

includes taxes & fees

5 Jan - 6 Jan

About this property

Hotel with 2 outdoor swimming pools, steps from South Beach

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.

Our customers tell us they enjoy the free breakfast at Southwinds Motel. During your stay, you're just a quick walk from Duval Street. Enjoy features like 2 outdoor pools, a bar, and concierge services.

Free continental breakfast served daily
Enjoy drinks at the bar/lounge
Take a swim in the 2 outdoor pools
Services include a concierge, tour or ticket assistance, and luggage storage
Onsite recreation includes bike rentals
Guests really like the accommodations for the comfy beds and cleanliness
Steps from South Beach and 3 minutes by foot from Duval Street

Southwinds Motel offers its guests 2 outdoor swimming pools. You can enjoy a drink at the bar/lounge. Free breakfast is available daily.

A vending machine, multilingual staff, and tour/ticket assistance are also featured at Southwinds Motel.

Smoking is allowed in designated areas at this Key West hotel.

Guests are served free continental breakfast daily from 7:00 AM to 10:00 AM.

Tipsy Rooster - This bar serves light fare only.

Languages

English, Russian, Spanish

Property amenities

Parking and public transport

Limited on-site parking
Wheelchair-accessible parking available

Food and drink

Free continental breakfast available daily 7:00 AM–10:00 AM
1 bar
Coffee/tea in a common area

Restaurants on site

Tipsy Rooster

Things to do

2 outdoor pools
Bike rentals

Family friendly

2 outdoor pools
Free cots/infant beds
High chair
Laundry facilities
Microwave
Pool gate
Fridge

Conveniences

Free newspapers in reception
Vending machine

Guest services

24-hour front desk
Concierge services
Housekeeping (on request)
Laundry facilities
Luggage storage
Multilingual staff
Tour/ticket assistance

Outdoors

Beach loungers
Outdoor entertainment area
Outdoor furniture
Picnic area
Pool sunloungers
Pool umbrellas

Accessibility

If you have any requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
This property does not have any lifts
Wheelchair-accessible parking

Beach towels
Designated smoking areas
Romance packages available

Room amenities

Bedroom

Air conditioning
Bed sheets
Down duvet
Free cots/infant beds
Pillow-top mattress
Premium bedding

Bathroom

Free toiletries
Hairdryer
Private bathroom
Shower
Towels

Entertainment

32-inch LED TV
TV channels

Food and drink

Cleaning supplies
Coffee/tea maker
Microwave
Paper towels
Fridge

Access via exterior corridors
Electrical adapters/chargers
Free local calls
Individually decorated
Individually furnished
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

No pets allowed

Children and extra beds

Children are welcome.

Kids stay free! Children 13 years old and younger stay free when using existing bedding.

Rollaway/extra beds are not available.

Free cribs (infant beds)!

Payment types at the property

Important information

Fees

Guests will be asked to pay the following charges at the property:

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've listed all charges provided to us by the property.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.

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

Front desk staff will greet guests on arrival.

We should mention

Children 13 years old and younger stay free in the same room as the parent or guardian when using existing bedding.
Registered guests are the only ones allowed to be in guestrooms.
Alcohol isn't served at Southwinds Motel.

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

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

4/10 Poor

Julie

22 Sept 2024

Stayed 1 night in Sep 2024

6/10 Okay

Darrell

21 Sept 2024

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

Travelled with partner

21 Sept 2024

Liked: Cleanliness, staff & service, property conditions & facilities

Favorite place in I stay

Stayed 7 nights in Sep 2024

10/10 Excellent

Jenna

Travelled with family

20 Sept 2024

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

19 Sept 2024

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

19 Sept 2024

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

Travelled with partner

19 Sept 2024

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 traveller

Travelled with family

18 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Stayed 1 night in Sep 2024

10/10 Excellent

Debra

Travelled with group

18 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

It was a little hard to park sometimes but we managed.

Stayed 5 nights in Sep 2024

10/10 Excellent

Socratise

Travelled with partner

16 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Beautiful well-maintained Property with polite and friendly staff. My first time to the Keys and will definitely use them again when I return.

Stayed 5 nights in Sep 2024

10/10 Excellent

Mitzi

Travelled with partner

15 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

This place was great we will be back

Stayed 3 nights in Sep 2024

10/10 Excellent

Lori, MIDDLETOWN

15 Sept 2024

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 7 nights in Sep 2024

8/10 Good

Shelly

14 Sept 2024

Stayed 5 nights in Sep 2024

10/10 Excellent

Frank

14 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Amazing 24 hour staff to answer all your questions and satisfy your needs

Stayed 7 nights in Sep 2024

10/10 Excellent

GLADYS

Travelled with group

13 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

This property was very clean. The staff was very nice. It was close to everything and very convenient. It was lovely. We arrived early and they let us keep our luggage in the office.

Stayed 1 night in Jul 2024

8/10 Good

Theresa

9 Sept 2024

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 6 nights in Sep 2024

10/10 Excellent

Jesse

9 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Love love this place I had the best time here will definitely return Thanks Sout Winds for a fabulous vacation see you next year !!

Stayed 4 nights in Sep 2024

10/10 Excellent

Michael, Locust Grove

9 Sept 2024

Liked: Cleanliness, staff & service, property conditions & facilities

Will stay here again for sure. Great value for only being a block off of Duval St. There is parking if needed as well.

Stayed 1 night in Aug 2024

10/10 Excellent

DEAN

Travelled with partner

7 Sept 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

better showers in room.

Stayed 7 nights in Aug 2024

8/10 Good

Aaron

Travelled with partner

7 Sept 2024

Liked: Amenities

Property was good, staff were very friendly and helpful. Room was a little small but fine for what we needed on our budget. Fridge and microwave in the room which was great. Breakfast was goo, help yourself continental style, no excuse if you left hungry. A bit of a walk in to town but ok if you like a walk.

Stayed 3 nights in Aug 2024

6/10 Okay

Ronald

6 Sept 2024

Liked: Staff & service, room comfort

Disliked: Cleanliness

Stayed 1 night in Sep 2024

8/10 Good

Brant Scott

5 Sept 2024

Liked: Cleanliness, staff & service

Stayed 5 nights in Aug 2024

10/10 Excellent

Debra

3 Sept 2024

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

Stayed 1 night in Sep 2024

8/10 Good

Kimberly

Travelled with group

3 Sept 2024

Liked: Staff & service, amenities, property conditions & facilities

This is not the fanciest of hotels but I would stay again. There's a musty scent in the room which may just be part of staying in KW on the south side of the island. 3 pools which are nicely maintained and the staff is friendly. Liquor store & bar on premise are great and the little convenience store and deli directly across the street are great options. There's a great coffee cart down the street by the Southern tip (highly recommend.) If you are looking for fancy, this isn't your place but if you are looking for charming convenience and a steal - this is the place for you.

Stayed 3 nights in Aug 2024