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Southwinds Motel

2.0 star property
Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Photo gallery for Southwinds Motel

Exterior
Exterior
Property grounds
2 outdoor pools, pool umbrellas, sun loungers
Reception

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry

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.)
    ‪7 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
(94 reviews)
  • 250 sq ft
  • 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
(69 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
(103 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
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Mallory Square - 4 min drive - 1.3 miles

Getting around

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

Restaurants

  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk
  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪La Te Da - ‬5 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach
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 grounds
The Palms Hotel
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  • Breakfast included
  • Pet friendly
  • Free WiFi
8.8 out of 10, Excellent, 1,000 reviews
$197 nightly
The price is $221
Nov 11 - Nov 12
Total with taxes and fees
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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
  • Bicycle rentals

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

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 Nov 7, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Nov 18, 2025 start from $134.49, 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 there parking available 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.

Is Southwinds Motel good for couples?

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.

Does Southwinds Motel have connecting rooms?

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, at Southwinds Motel, there aren't any guestrooms that list a balcony.

Reviews

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
Rating 10 - Excellent. 713 out of 1226 reviews
Rating 8 - Good. 318 out of 1226 reviews
Rating 6 - Okay. 127 out of 1226 reviews
Rating 4 - Poor. 50 out of 1226 reviews
Rating 2 - Terrible. 18 out of 1226 reviews

Reviews

8/10 Good

Craig

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Aug 2025

10/10 Excellent

Cynthia

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay
Stayed 5 nights in Jul 2025

6/10 Okay

Louise

Traveled with family
Liked: Cleanliness, staff & service
Disliked: Amenities
the room we were given was not handicap friendly. the pool outside our door was out of order. the step into the room was hard to manage with my walker. The girl at check-in was not very friendly and seemed bothered. Nowhere in the room for a handicap person to sit. Brought a chair in from the pool.
Stayed 1 night in Jul 2025

4/10 Poor

Alexandre

Liked: Staff & service
Bed bug on myself and my pregnant wife. :(
Stayed 1 night in Jul 2025

10/10 Excellent

George

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

Southwinds motel

The stay was excellent as the well as the location and the grounds. Staff was helpful as well .The value was a good
Stayed 4 nights in Jul 2025

4/10 Poor

Keith

Traveled with family
Disliked: Property conditions & facilities
We were asked when checking in if we used Orbitz, I said yes and she changed my room number. Room assignment was not what was shown on the website or in the photos.
Stayed 5 nights in Jul 2025

10/10 Excellent

Mike

Liked: Cleanliness, staff & service, property conditions & facilities
Was close to Duval st to walk. Bar on property was nice and once in the room really couldn't hear the outaide noise which was nice
Stayed 1 night in Aug 2025

10/10 Excellent

Cynthia

Stayed 2 nights in Aug 2025

10/10 Excellent

Verified traveler

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

several suggestions impovement

I would strongly advise installing safety bars in the shower as it is very slippery and I almost slipped and fell several times...nothing to hold on to. A better handle on the cockroach situation as well as we killed 4 of them in our room for a 5 day stay.
Stayed 5 nights in Jul 2025

10/10 Excellent

Anna

Liked: Cleanliness, staff & service, property conditions & facilities
This was a great place to stay especially for the price! Clean and comfortable. A bit of a walk to get to Mallory Square and the end of Duval, but we enjoyed the exercise. Plenty of places close by and the property has a bar. Ice machines weren’t really working so that was the only bummer. Staff was super friendly and helpful!
Stayed 2 nights in Jul 2025

4/10 Poor

rose marie

Traveled with family
Liked: Cleanliness
Disliked: Property conditions & facilities
Bathroom door does not lock, bathroom looks old, front door does not have a secure lock.
Stayed 1 night in Jul 2025

8/10 Good

Valery

Liked: Staff & service
Disliked: Property conditions & facilities
Really liked everything but the futon
Stayed 5 nights in Jul 2025

10/10 Excellent

Joanne

Stayed 3 nights in Jul 2025

6/10 Okay

Deborah

Traveled with partner
Liked: Cleanliness
The staff was fine, not particularly friendly. Parking was not good. The second pool was out of order, so the one pool was crowded.
Stayed 1 night in Jul 2025

4/10 Poor

PAM

Traveled with group
Disliked: Property conditions & facilities
Bathrooms extremely small and very old, no updates. Decorative Pillows on bed were dirty.
Stayed 2 nights in Jul 2025

10/10 Excellent

Keithia

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Jul 2025

8/10 Good

Michel

Stayed 1 night in Jul 2025

10/10 Excellent

Jayne

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

Had a great time as usual

The last 2 times we went this year. We traveled thru the night to get there by car. We live in South west Florida. They got us in the room right away! 9am! So grateful for the ladies in the office. So friendly
Stayed 3 nights in Jun 2025

10/10 Excellent

Frank

Liked: Cleanliness, staff & service, property conditions & facilities
The property was great and everyone was friendly and they had music, food right across the street and around the coner.
Stayed 4 nights in Jul 2025

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, property conditions & facilities
property is close to many of the restaurants that i frequent. Being a solo traveler I feel safe at this property
Stayed 5 nights in Jul 2025

8/10 Good

Varun

Traveled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Motel has been well maintained and the staff are very helpful. Location is great.
Stayed 1 night in Jul 2025

10/10 Excellent

Ashley

Liked: Cleanliness, staff & service, property conditions & facilities
While the property is older the rooms were clean and cold which was much appreciated. Staff was excellent and friendly. I was a little worried as the seal around the doors and the AC unit could stand to be addressed but no issues and the room served it's purpose. The TV is very small but who goes to Key West to watch TV? Overall I was pleasantly surprised and would stay at the motel again.
Stayed 2 nights in Jul 2025

10/10 Excellent

Autumn

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was perfect!
Stayed 4 nights in Jul 2025

10/10 Excellent

lisa

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay right in the mix of everything to do!! Staff was great love smaller mom and pop places to stay
Stayed 3 nights in Jul 2025

4/10 Poor

Aneta

Disliked: Cleanliness, property conditions & facilities, room comfort

Disappointing Stay-Needs Serious Upgrades

I rarely leave negative reviews, but this hotel was truly below acceptable standards. The room was in dire need of upgrades — everything felt old, worn down, and poorly maintained. The floor was filthy when we arrived, and to make matters worse, the tub still had hair in it from a previous guest. That alone was enough to make me question the cleanliness of the entire room. The AC unit was not properly insulated, and during a thunderstorm, rainwater actually started leaking in through the unit. It was a huge mess and made us feel completely uncomfortable and unsafe. The pool was also a major letdown. It looked unkempt and murky, clearly not cleaned or properly maintained on a regular basis. We had looked forward to using it, but after seeing the condition, we decided it wasn’t worth the risk. Overall, I would not recommend staying here unless significant improvements are made. Cleanliness and basic maintenance should be a priority — unfortunately, this hotel failed on both fronts.
Bathroom tile
Walked from the bathroom to the bed barefoot.
Stayed 4 nights in Jul 2025

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