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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
Front of property
Property grounds

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar

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
(102 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

8.6 out of 10
Excellent
(74 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
(109 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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About the neighborhood

Key West

Located in Old Town Key West, Southwinds Motel is adjacent to South Beach and within a 5-minute walk of other popular sights like Duval Street. This 58-room hotel welcomes guests with 2 outdoor pools, free breakfast, and a bar/lounge.

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
  • ‪Banana Cafe - ‬4 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk

About this property

Southwinds Motel

Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. Self parking is offered for USD 22.50 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. Additional amenities include laundry facilities, a picnic area, and a vending machine.
Guests can expect to find 32-inch LED TVs with cable channels. Bathrooms offer hair dryers and free toiletries, and pillowtop beds with premium bedding and down comforters ensure a restful night. Other standard amenities include refrigerators, microwaves, and coffee makers. Housekeeping is available on request.
2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

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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

  • This property doesn't allow pets

Children and extra beds

  • Free cribs/infant beds are available

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

  • 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

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Self parking fee: USD 22.50 per day

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM—-midnight
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day. Driving? This property offers parking (fees apply).

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • The minimum check-in age for Spring Break is 18 years old.
  • This property accepts credit cards, debit cards, and cash.
  • The credit card used at check-in for incidentals must be in the name of the primary guest who made the reservation.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Additional information about polices, regulations, and more:

  • Registered guests are the only ones allowed in guestrooms.
  • No alcohol is served at Southwinds Motel.
  • There are no elevators.
  • No rollaway or extra beds are available.

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

Frequently asked questions

Is a free cancellation option available at Southwinds Motel?

Southwinds Motel offers free cancellation on some room rates. For specific requirements, look at the cancellation policy on Orbitz.

How much does it cost to stay at Southwinds Motel?

As of Feb 23, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Feb 25, 2026 start from $353.49, excluding 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.

What's there to do around Southwinds Motel?

This hotel is situated in Old Town Key West, just steps from Duval Street and Florida Keys Beaches, and within a short walk of South Beach. You'll also find Southernmost Point and Ernest Hemingway Home and Museum less than a mile away.

Is parking available on site at Southwinds Motel?

Yes, parking is offered for USD 22.50 per day.

Does Southwinds Motel have a casino at the property?

No, Southwinds Motel doesn't have a casino.

Will I find an indoor pool at Southwinds Motel?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools.

What do couples enjoy most about Southwinds Motel?

There are plenty of amenities for couples at this hotel, including 2 outdoor pools, a bar, and proposal/romance packages.

Does Southwinds Motel have a hot tub?

No, this hotel doesn't have a spa tub.

Does Southwinds Motel feature a restaurant that includes a breakfast menu?

Yes, Southwinds Motel serves free continental breakfast at Tipsy Rooster each morning.

Will Southwinds Motel allow pets to stay free of charge?

No, pets aren't allowed at Southwinds Motel.

Are there connecting rooms at Southwinds Motel?

No, there aren't connecting guestrooms at this hotel.

How close is the airport from Southwinds Motel?

The closest major airport to Southwinds Motel is Key West Intl. Airport (EYW), which is 3.2 mi away (8 minutes by car).

Are there rooms with balconies that I can book at Southwinds Motel?

No, there aren't any guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 734 out of 1289 reviews
Rating 8 - Good. 336 out of 1289 reviews
Rating 6 - Okay. 142 out of 1289 reviews
Rating 4 - Poor. 55 out of 1289 reviews
Rating 2 - Terrible. 22 out of 1289 reviews

8.8/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

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

10/10 Excellent

Lisa

Traveled 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

8/10 Good

Dennis

Liked: Cleanliness, property conditions & facilities
Room was large and clean
Stayed 2 nights in Nov 2025

8/10 Good

Sally

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic location and friendly staff.
Stayed 4 nights in Oct 2025

10/10 Excellent

Gerry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great little place. It's got a bit of that old Key West flavor that's getting harder and harder to find. Great staff...friendly and helpful. Go here. It's cool.
Stayed 2 nights in Nov 2025

10/10 Excellent

Carissa

Liked: Cleanliness, staff & service, amenities
Stay was wonderful. Staff was very accommodating and helpful. Room is spacious and clean with serviceable fridge and microwave. Bathroom size could be bigger and would recommend checking shower drain for smell especially when not in used
Stayed 2 nights in Nov 2025

10/10 Excellent

Anita L

Traveled with family and small children
Liked: Cleanliness, amenities, property conditions & facilities
The room was great!
Stayed 1 night in Nov 2025

10/10 Excellent

Sanda

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff, location
Stayed 2 nights in Nov 2025

8/10 Good

Ivy

The staff is always very helpful and friendly at Southwinds Motel. Our room was accomodating but rather small for a double. And they need to put more hooks in the bathroom and a full length mirror in the room. There is nothing on the walls so there is room and a large mirror would be nice.
Stayed 3 nights in Nov 2025

10/10 Excellent

Julie

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We had a great stay for the weekend. We loved having the chairs and towels at the beach one block away. All of the employees were nice and helpful.
Stayed 3 nights in Nov 2025

8/10 Good

Ken

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfect location , Room's could use some updates, Very comfortable area.
Stayed 3 nights in Nov 2025

10/10 Excellent

Brenda

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Yes,breakfast was fresh.
Stayed 7 nights in Nov 2025

8/10 Good

Betty

Stayed 4 nights in Oct 2025

10/10 Excellent

Janice

Stayed 2 nights in Nov 2025

10/10 Excellent

Jessica

Stayed 1 night in Oct 2025

8/10 Good

Robert

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Nice motel traditional Key West building in a great position for downtown. Room was clean nice beds bathroom is very dated but clean. Staff were excellent.
Stayed 4 nights in Nov 2025

6/10 Okay

Linda

Liked: Cleanliness, staff & service
Room is very small with nowhere to put things. However it was clean. Excellent location for walking all around key West. Breakfast was small.
Stayed 2 nights in Nov 2025

8/10 Good

Dorothy, philadelphia

Liked: Cleanliness, amenities
Disliked: Property conditions & facilities
The place is Old. It was clean. You will find rust, chips in the floors, water pressure in the shower(room 33) very bad. The price & location Great. The small pool, was never useable for the 7 nights we were there. It was Green & cold. The continental breakfast & parking are worth it alone. I would stay there again. I visit Key West one or two times a year.
Stayed 7 nights in Nov 2025

10/10 Excellent

Carla, Monroeville

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Location was exactly what we were looking for. Close enough to walk to everything yet away from the noise and bars of Duval street. Great room, staff and amenities. Pool was nice, clean and water temp was perfect. Definitely staying here again.
Stayed 4 nights in Oct 2025

10/10 Excellent

Mary

Traveled with group
Liked: Cleanliness, staff & service, amenities
Roomwas clean! Great location
Stayed 2 nights in Nov 2025

8/10 Good

Tara

Liked: Cleanliness, staff & service
We love our stay at Southwinds. There are a couple things that could make it much better: 1. Some hooks on the shower door or bathroom wall for towels. 2. A bit more water pressure or a new shower head. Other than that - it's always a pleasure staying at Southwinds. We love the location. It's quiet. It's in walking distance to many of the locations we love. The Tipsy Rooster is a great bonus also. The beds are comfortable. The AC works great. The pools are amazing.
Stayed 5 nights in Nov 2025

10/10 Excellent

Shane

Stayed 4 nights in Nov 2025

10/10 Excellent

Jeanne

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Everything about this place was perfect!
Stayed 4 nights in Nov 2025

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, amenities
Keep in mind it’s a motel! Staff were very friendly and the place was clean, as was the bathroom. Never entertained the two pools they have but people seemed to enjoy them. I think my only don’t is the property owns a bar next door and if your room is next to it - it can be quite noisy. Otherwise if ya not looking for all the fancy frills go for it, I’d stay again. They accommodate parking too, we rented a golf cart and it was no problem parking on the property. Enjoy!
Stayed 3 nights in Oct 2025

10/10 Excellent

Laura E

Stayed 2 nights in Nov 2025

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