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Southwinds Motel

2.0 star property

Photo gallery for Southwinds Motel

Bar (on property)
Front of property
Property grounds
Reception
Standard Room, 2 Queen Beds

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air-conditioning
  • Bar

Explore the area

View 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 duvets, pillow-top beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(105 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(78 reviews)
  • 37 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

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

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Standard Room, 1 King Bed

8.4 out of 10
Very good
(112 reviews)
  • 28 sq m
  • Sleeps 3
  • 1 King Bed

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About the area

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 - 0.3 km
  • South Beach - 3 min walk - 0.3 km
  • Southernmost Point - 5 min walk - 0.4 km
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km

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
  • ‪Banana Cafe - ‬4 min walk
  • ‪Southernmost Point Bar in the USA - ‬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 transport

  • Parking on site (USD 22.50 per day)
  • Limited on-site self parking

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 cot
  • 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 lift

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free cot
  • 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

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. 719 out of 1293 reviews
Rating 8 - Good. 346 out of 1293 reviews
Rating 6 - Okay. 147 out of 1293 reviews
Rating 4 - Poor. 57 out of 1293 reviews
Rating 2 - Terrible. 24 out of 1293 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

4/10 Poor

Thomas, Warwick

Put us in a room right next to bar that had extremely loud music till 1-2 AM, also outside lights on all night and it was like daytime in the room, even with blinds closed, no drapes, made reservations for 2 rooms months earlier and our friends were the farthest room away from us
Stayed 2 nights in Dec 2025

6/10 Okay

Crystal

Travelled with partner
Liked: Cleanliness, property conditions & facilities
Disliked: Amenities
The room is small but clean with everything you need. The hotel is very cute. The evening staff was extremely rudechecknin was rud
Stayed 1 night in Dec 2025

10/10 Excellent

Gaston

Liked: Cleanliness, amenities, property conditions & facilities
Great location and well maintained. Breakfast does the job.
Stayed 1 night in Dec 2025

8/10 Good

Susan

Travelled with family
Liked: Cleanliness, staff & service, amenities
Overall the place was nice, you could tel they try hard to make it nice. They could dim the outdoor lights a little in the evening so they don't come through the blinds at night time though! The evening clerk wasn't very cheery...at all. She was there LOL Breakfast is basically wrapped pastries, fruit and yogurt, juice.....really a continental breakfast. We decided to pass and go to Frenchies!! YUM! The rooms were clean, beds were firm, pillows were decent and plentiful. We only stayed a night, but that's all i'd really stay for if it were a longer vacation i'd stay somewhere else. They hit you with a $30 service fee and another $25 for something else right when you check in....so be aware of that. We did book through Expedia. You can hear people knocking on other doors...thinking it might be your own....BUT as I said it was one night, the price was right until we got hit with the other fees.... Clean, safe, and close to the southernmost point and Dumont st.
Stayed 1 night in Dec 2025

10/10 Excellent

Denna

Travelled with family
Liked: Cleanliness, property conditions & facilities
Cute comfortable rooms great staff and great location!! Will stay again
Stayed 1 night in Dec 2025

10/10 Excellent

William

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great location. Decent facilities. Wonderful staff. Not a bad price considering key west.
Stayed 2 nights in Dec 2025

2/10 Terrible

Rosalind

Disliked: Cleanliness
Stayed 1 night in Dec 2025

8/10 Good

Charles

Liked: Staff & service, room comfort
Did not eat breakfast there
Stayed 2 nights in Dec 2025

10/10 Excellent

THERESA

Liked: Cleanliness, amenities, property conditions & facilities
Staffs are friendly. The room is clean and breakfast is fantastic
Stayed 1 night in Dec 2025

8/10 Good

anna

Liked: Cleanliness, staff & service, amenities
Clean nice motel
Stayed 6 nights in Dec 2025

10/10 Excellent

Stefanie J

Liked: Cleanliness, staff & service, amenities
The room was great, and the staff was so helpful. It is at a great location. It offers free parking, which is wonderful!
Stayed 3 nights in Dec 2025

10/10 Excellent

darrin

Liked: Cleanliness, amenities, property conditions & facilities
Staff was great
Stayed 3 nights in Dec 2025

10/10 Excellent

Adam

Stayed 3 nights in Dec 2025

6/10 Okay

April, Wood Dale

Travelled with partner
Air conditioner broke. Water on the floor. Service man was helpful with the tv not working and moving us to another room. Pool temp was nice.
Stayed 1 night in Dec 2025

10/10 Excellent

Lisa

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Our stay at Southwinds hotel was wonderful. The staff always treats as courtesy since we booked through orbits we were allowed to pick our room once we arrive there great place to stay great pick up and go breakfast in the morning and close to several fun activities.
Stayed 7 nights in Dec 2025

10/10 Excellent

Linda

Travelled with group
Liked: Cleanliness, amenities, property conditions & facilities
Room was clean, staff was very nice. Breakfast offered was basic but fine. Location was perfect with Tipsy Rooster Liquor Store and bar next door. The store across the street was an extra bonus.
Stayed 7 nights in Nov 2025

10/10 Excellent

Aaron

Stayed 1 night in Dec 2025

10/10 Excellent

Denise

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
It is a charming motel, impeccable cleanliness, and enjoyed the friendliness of the staff! We were pleasantly pleased with the location of one block from Duvall Street.
Stayed 1 night in Dec 2025

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities
Always a great stay at the Sea Oats.
Stayed 3 nights in Dec 2025

10/10 Excellent

Hailey

Liked: Cleanliness, amenities, property conditions & facilities
Perfect little place, great location!
Stayed 2 nights in Dec 2025

2/10 Terrible

Stephen

Travelled with partner
Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities
We were jolted awake by a faulty fire alarm at 1am in the morning. The breakfast was presented in the small lobby and nowhere to sit except outside but all seats were wet due to rain. Our hotel room was very small and the bathroom had bugs which got into my shaving kit. Although I liked the old style cottages, for the price this place was not worth it.
Stayed 1 night in Dec 2025

6/10 Okay

Karl

Travelled with family
Liked: Cleanliness, amenities
Ok spot to stay. Tiny room. Weak water pressure in shower but I expected that. Staff wanted to charge me 20$ to park my rental car which I thought was outrageous. Put a 150$ hold on cc as soon as you check in. I’ve not seen the credit applied back as quickly. Tippys rooster was nice being part of motel. As the kids say. This place was mid.
Stayed 1 night in Dec 2025

10/10 Excellent

Sherri

Liked: Cleanliness, amenities, property conditions & facilities
Rooms were clean and comfortable. The staff was so friendly and accommodating. Sightseeing and restaurants were all close by. We would definitely stay there again.
Stayed 1 night in Dec 2025

10/10 Excellent

William

Stayed 7 nights in Dec 2025

10/10 Excellent

joan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Really sweet little place with fantastic beach access. The beach is a block away but the hotel provides free towels and long chairs with umbrellas. Nice cuban deli across the street. Close to Duval but without its busy-ness.
Stayed 4 nights in Nov 2025