See all properties

Southwinds Motel

2.0 star property

Choose dates to view prices

Photo gallery for Southwinds Motel

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

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

8.2 out of 10
Very good
(103 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
(75 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

You may also like

Ad
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)

Blue Flamingo Resort Key West

New Town
  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
8.2 out of 10, Very Good, 1,980 reviews
$328 nightly
The price is $369
Mar 10 - Mar 11
Total with taxes and fees
Blue Flamingo Resort Key West

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.

Similar properties

Lobby
Authors of Key West Guest House
  • Pool
  • Breakfast included
  • Free WiFi
  • Restaurant
9.0 out of 10, Wonderful, 1,008 reviews
$259 nightly
The price is $291
Apr 8 - Apr 9
Total with taxes and fees
Authors of Key West Guest House

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 9, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Apr 5, 2026 start from $362, 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.

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 at Southwinds Motel?

No, at Southwinds Motel, there aren't any guestrooms that list a balcony.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 733 out of 1298 reviews
Rating 8 - Good. 340 out of 1298 reviews
Rating 6 - Okay. 145 out of 1298 reviews
Rating 4 - Poor. 57 out of 1298 reviews
Rating 2 - Terrible. 23 out of 1298 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

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

10/10 Excellent

James

Traveled with partner
Liked: Cleanliness, staff & service, amenities
Nice breakfast and room was nice. Only problem was parking was tight on the side of the hotel we was on. Hotel was in a very nice area and the staff was very good.
Stayed 2 nights in Nov 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

Hotels