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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

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

Reviews

8.6 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.)
    ‪12 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
(109 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
(80 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
(116 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

  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬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 tours/tickets 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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Wicker Guesthouse
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  • Pet friendly
  • Parking included
8.6 out of 10, Excellent, 1,002 reviews
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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 May 21, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Jun 21, 2026 start from $196, 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 Florida Keys Beaches and Duval Street, 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.

Will I be able to park 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 a good place to stay for couples?

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

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 available?

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).

Can I book a room with a balcony at Southwinds Motel?

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

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 749 out of 1356 reviews
Rating 8 - Good. 364 out of 1356 reviews
Rating 6 - Okay. 154 out of 1356 reviews
Rating 4 - Poor. 60 out of 1356 reviews
Rating 2 - Terrible. 29 out of 1356 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

8/10 Good

Michele

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the liquor store/bar on property that had live music during our stay. Across the street from a small market and walking distance to beach with chairs and umbrellas. The room was incredibly small but in fairness it worked for us. We showered and slept in the room so didn’t need much. The air conditioner had a hard time keeping the room cool but we found it acceptable. The pool was nice and the staff very friendly.
Stayed 3 nights in May 2026

8/10 Good

Steven

Liked: Cleanliness, staff & service, amenities
Great place - can walk to most activities- place a bit dated - decent breakfast- staff super friendly- would stay again.
Stayed 2 nights in Apr 2026

10/10 Excellent

Shawn

Stayed 1 night in Dec 2025

10/10 Excellent

Alexandria

Stayed 2 nights in Jan 2026

8/10 Good

Kerry

Traveled with partner
Liked: Cleanliness, amenities
The staff was great, very courteous and helpful. The room needs some attention. Bathroom sink too low and small and faucet needs replaced. Both faucets in shower need replaced. It was very hard to maintain constant water temperature while showering. It would have been helpful to have had more storage for clothes rather than "living out of the suitcase."
Stayed 4 nights in Feb 2026

4/10 Poor

brian

Disliked: Amenities
Room very tired, initially the shower wasn’t hot, maintenance called, temperature sorted but no water pressure. The room was next to a bar so very loud music until around midnight. Wouldn’t recommend this hotel, the only good thing was the location, walking distance to Duval Street
Stayed 1 night in Feb 2026

10/10 Excellent

Leyany

Traveled with partner
Liked: Cleanliness, amenities
Very convenient location
Stayed 1 night in Feb 2026

10/10 Excellent

Debra

Traveled with family
Liked: Cleanliness, staff & service, amenities
Best place for price. Love rooms 1 and 2
Stayed 2 nights in Jan 2026

8/10 Good

Leah

Stayed 3 nights in Feb 2026

6/10 Okay

OSCAR

Liked: Cleanliness, staff & service
Not sure why this place charges a “resort fee” upon check in (I was charged $156 for three nights). This is an old motel with many upgrades and improvements needed. My positive is that everyone at the front desk was helpful and friendly
Stayed 3 nights in Feb 2026

10/10 Excellent

Laura

Liked: Cleanliness, amenities, property conditions & facilities
Clean rooms, hot showers, friendly staff, great location! The Tipsy Rooster was a bonus 🙂
Stayed 7 nights in Feb 2026

8/10 Good

JANET

Traveled with partner
Liked: Cleanliness
Location to Duvall street and other sites.
Stayed 2 nights in Feb 2026

8/10 Good

Kristin

Liked: Cleanliness, property conditions & facilities
Allowed to store luggage for the day
Stayed 2 nights in Feb 2026

8/10 Good

Michael L

Liked: Cleanliness
Location
Stayed 14 nights in Jan 2026

8/10 Good

Robert, Springfield

Stayed 5 nights in Feb 2026

10/10 Excellent

JD

Stayed 3 nights in Oct 2025

8/10 Good

Stacy

Stayed 3 nights in Feb 2026

10/10 Excellent

Judy

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The room was very nice and had everything we needed. Checking in and out was so quick and easy with very friendly employees. The breakfast was excellent with plenty of good choices. The location was great with easy walk or bike ride to most things.
Stayed 4 nights in Feb 2026

8/10 Good

Grady

The rooms were clean, the staff was polite and helpful, and the provided light breakfast options provided were good.
Stayed 7 nights in Feb 2026

10/10 Excellent

Valerie

Liked: Cleanliness, amenities, property conditions & facilities
Friendly and helpful staff.
Stayed 8 nights in Jan 2026

10/10 Excellent

Deborah

Liked: Cleanliness, amenities, property conditions & facilities
Great location and comfortable stay.
Stayed 3 nights in Feb 2026

8/10 Good

Thomas

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Older motel, rooms are kinda small but everything was clean, staff was great, even had free use of laundry facilities, decent breakfast selection with nearby options also available.
Stayed 7 nights in Feb 2026

6/10 Okay

Hunter

Stayed 7 nights in Feb 2026

8/10 Good

William

Stayed 1 night in Feb 2026

8/10 Good

Shelly

Traveled with group
Liked: Cleanliness, amenities
Rooms were clean. The bed need replaced. The area was great.
Stayed 8 nights in Jan 2026

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