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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

Bar (on property)
Front of property
Property grounds
Reception
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated

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
(104 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

8.8 out of 10
Excellent
(77 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
(111 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 Mar 16, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Apr 5, 2026 start from $358, including 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, there isn't a spa tub at this hotel.

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 at Southwinds Motel?

No, you won't find guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 725 out of 1289 reviews
Rating 8 - Good. 338 out of 1289 reviews
Rating 6 - Okay. 146 out of 1289 reviews
Rating 4 - Poor. 57 out of 1289 reviews
Rating 2 - Terrible. 23 out of 1289 reviews

8.8/10

Cleanliness

9.0/10

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

10/10 Excellent

Linda

Traveled 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

Traveled 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

Traveled 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

Traveled 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

10/10 Excellent

Michelle

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Great location! Bar with live entertainment! Clean room! Two pools! It was perfect for my husband and me.
Stayed 1 night in Dec 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Most hotels off full breakfast now. Blinds weren’t room darkening so room was lit up all night
Stayed 1 night in Dec 2025

8/10 Good

Josh

Stayed 4 nights in Nov 2025

10/10 Excellent

Shawn

Liked: Cleanliness, amenities, property conditions & facilities
Great place! Clean room. Friendly staff. And a bar right out front of motel. What more could you want?? Highly recommend this place. Quiet area of KW. Away from all the hoopla
Stayed 7 nights in Nov 2025

4/10 Poor

Harry

Traveled with partner
Liked: Cleanliness, staff & service
Disliked: Amenities, property conditions & facilities
We were in a room that was very old and outdated and small. Need to demolish the older rooms and start over.
Stayed 2 nights in Nov 2025

8/10 Good

Rodney

Traveled with group, Traveled with partner, Traveled with family
Liked: Cleanliness, property conditions & facilities
Staff was great. Room was clean. Location was pretty good too. Breakfast was pretty much all “grab and go” but had a decent selection. Overall it was a very good stay and hard to beat for the price.
Stayed 3 nights in Nov 2025

10/10 Excellent

Tuing

Stayed 1 night in Nov 2025

2/10 Terrible

Edward

Traveled with group
Disliked: Cleanliness, amenities, property conditions & facilities
We had to ask to get our room cleaned and to get clean towels. We were also told at check in there was a $20 a day parking fee, in which was waved when I said to cancel my reservation. The bathroom plumbing was a less than adequate with no hot water on the last two days. No quiet time at night with younger guests being loud and obnoxious at 1/2AM in the morning. I could go on, but just to say our stay was very nupleasant is an understatement and I'm very unhappy that we spent that much money for that kind of service. I will not be booking that property again. I'm more than dissatisfied and I truly this reaches someone that cares. Thankyou.
Stayed 4 nights in Nov 2025

8/10 Good

Russell

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Room was clean, and the front desk staff was very nice.
Stayed 1 night in Nov 2025

6/10 Okay

Koichi

Stayed 1 night in Nov 2025

10/10 Excellent

rafel

Liked: Cleanliness, staff & service, amenities
nice place
Stayed 1 night in Nov 2025

10/10 Excellent

Holly, Apache Junction

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was so nice, great location.
Stayed 3 nights in Nov 2025

6/10 Okay

Samuca

Location was perfect. However when we arrived in the room there were no towels and no soap to take a shower. In addition, breakfast selection wasn’t good at all. We were put in a room behind a bar and it was extremely loud until 2am in the morning.
Stayed 2 nights in Nov 2025

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