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Southwinds Motel

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

Photo gallery for Southwinds Motel

Exterior
Deluxe Room | Living area
Exterior
2 outdoor pools, pool umbrellas, pool loungers
Standard Room, 2 Queen Beds

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning
The current price is AU$269
includes taxes & fees
11 June - 12 June

Explore the area

Map
1321 Simonton Street, Key West, FL, 33040
  • Duval Street
    ‪3 min walk‬
  • South Beach
    ‪3 min walk‬
  • Southernmost Point
    ‪5 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Room options

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Standard Room, 1 King Bed

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Renovated in 2016
Separate bedroom
  • 28 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for Deluxe Room

1 bedroom, premium bedding, down duvets, pillow-top beds

Deluxe Room

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Pillow-top bed
Premium bedding
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Ceiling fan
Premium bedding
  • 37 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 Queen Bed

1 bedroom, premium bedding, down duvets, pillow-top beds

Standard Room, 1 Queen Bed

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Ceiling fan
Premium bedding
  • 23 sq m
  • Sleeps 3
  • 1 Queen Bed

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About the area

Key West

Southwinds Motel places you steps from South Beach and within a short 5-minute stroll of Duval Street. Highlights at this hotel include 2 outdoor swimming pools and free continental breakfast. .Tipsy Rooster is the hotel's own bar, serving drinks along with light fare. Other amenities include coffee/tea in a common area and laundry facilities. Each morning free breakfast is served. There's also the convenience of limited parking. .Places within a short walk of this Old Town Key West hotel include Southernmost Point and Ernest Hemingway Home and Museum is within 15 minutes.

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • South Beach - 3 min walk - 0.3 km
  • Southernmost Point - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 4 min drive - 2.0 km

Getting around

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

Restaurants

  • ‪El Siboney Restaurant - ‬8 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Southernmost Point Bar In the USA - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬5 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach
Southwinds Motel offers its guests 2 outdoor swimming pools. You can enjoy a drink at the bar/lounge. Free breakfast is available daily.

A vending machine, multilingual staff, and tour/ticket assistance are also featured at Southwinds Motel.

Smoking is allowed in designated areas at this Key West hotel.

  • 1 floor
  • 58 guestrooms or units
  • 9 buildings
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Coffee in lobby
  • Self-service laundry
  • Front desk (24 hours)
  • Staff members are multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Outdoor picnic space
  • Newspapers in lobby (free)
  • Smoking in designated areas
  • Bar or lounge
Southwinds Motel offers 58 air-conditioned accommodations, which are accessible via exterior corridors, and features coffee/tea makers and a hairdryer. Each accommodation is individually furnished and decorated. Pillowtop beds feature down duvets and premium bedding. Guests can make use of the in-room fridges and microwaves. Bathrooms include a shower and complimentary toiletries.

32-inch LED televisions come with cable channels. Business-friendly amenities include telephones along with free local calls (restrictions may apply). Housekeeping is provided on request.

Languages

English, Russian, Spanish

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Property amenities

Parking and transport

  • Limited on-site parking
  • Wheelchair-accessible parking available

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
  • Free cot
  • Highchair
  • 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift
  • Wheelchair-accessible parking

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free cot
  • 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

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Access methods

Staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Kids stay free! Children 13 years old and younger stay free when using existing bedding.
  • Rollaway/extra beds are not available.
  • Free cots (infant beds)!

Payment types

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • Resort fee: USD 28.13 per accommodation, per night
The resort fee includes:
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access
  • Self-parking

We've listed all charges provided to us by the property.

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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 guest room reservation. This property accepts Visa, Mastercard, American Express, Discover, Diners Club, debit cards and cash. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation.

We should mention

  • Children aged 13 years old and younger stay free in the same room as the parent or guardian when using existing bedding.
  • Registered guests are the only ones allowed to be in guestrooms.
  • Alcohol isn't served at Southwinds Motel.

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

What is the cancellation policy at Southwinds Motel?

Southwinds Motel offers free cancellation on select room rates. Check out the cancellation policy for more info.

How much does it cost to stay at Southwinds Motel?

As of 10 June 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on 11 June 2025 start from AU$225.50, 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.

Is parking available at Southwinds Motel?

Onsite parking is limited.

Are there any beaches close to Southwinds Motel?

Yep, Southwinds Motel is a short 2-minute walk from Florida Keys Beaches. Fun beach activities include snorkelling, scuba diving and parasailing. You can also find boat tours.

Does Southwinds Motel have a pool?

Yep, and guests recommend it! Southwinds Motel has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying under the shade of an umbrella.

What makes Southwinds Motel a romantic place to stay?

Romance packages and a lounge bar, as well as pillowtop beds in the guestrooms, all help set the scene for a romantic weekend at Southwinds Motel.

Is Southwinds Motel family-friendly?

You bet! With amenities such as 2 outdoor pools and laundry facilities, as well as highchairs and free infant beds in the guestrooms, it's no surprise that Southwinds Motel is a hit with families.

Does Southwinds Motel serve breakfast?

Yeah, our visitors speak well of the free continental breakfast here! Served daily from 7:00 AM to 10:00 AM, this is the place to fuel up for a big day of adventure.

Is there a free airport shuttle available at Southwinds Motel?

No, Southwinds Motel does not offer an airport shuttle service.

What time are check-in & check-out at Southwinds Motel?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Are pets allowed at Southwinds Motel?

No, pets are not allowed.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 633 out of 1103 reviews
Rating 8 - Good. 289 out of 1103 reviews
Rating 6 - Okay. 119 out of 1103 reviews
Rating 4 - Poor. 44 out of 1103 reviews
Rating 2 - Terrible. 18 out of 1103 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

10/10 Excellent

Jason

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 4 nights in Mar 2025

8/10 Good

Linda

Liked: Cleanliness, staff & service, room comfort

Up and down

The check in process was easy. The property offers 2 pools,( 1 smaller heated one) which are clean, and a very basic continental breakfast with several comfortable outdoor areas. Unfortunately, maid service is only every 3 days, but we had to specifically ask for our room to be done because our room was not initally on the list for our 3rd day there. The room, itself, is clean, but is a very, very dated room with a tiny bathroom, though the bed is comfortable. The location is great and musical entertainment is offered daily as part of the complex, along with outdoor bar and pricy ice cream truck. The Cuban restaurant across the street is casual and delicious. The staff are very helpful and friendly.
Stayed 4 nights in Mar 2025

4/10 Poor

Patricia

Disliked: Property conditions & facilities
The property just needed maintenance. Bushes and landscaping needed attention. Seals around the door needed attention. General maintenance.
Stayed 2 nights in Mar 2025

10/10 Excellent

Jennifer

Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities
This was my 3rd time in Key West and the first time at Southwinds with my lifelong best friend of almost 50 years. Couldn’t have asked for better service, accommodations, location, comfort and all-around amazing! I highly recommend Southwinds. Definitely will return!
Stayed 4 nights in Feb 2025

10/10 Excellent

Pennie, Greensboro

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the location of this property. Just blocks away from Duval St and the beach.
Stayed 3 nights in Feb 2025

10/10 Excellent

William

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Mar 2025

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Feb 2025

8/10 Good

Martin

Travelled with partner
Disliked: Amenities
Whole property could use a paint job but beds we’re comfortable and shower was good. Heated pool was nice
Stayed 3 nights in Feb 2025

8/10 Good

Ramona

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful motel, well maintained. Staff was friendly.
Stayed 3 nights in Feb 2025

10/10 Excellent

Daniel

Liked: Staff & service
No frills vacation. Was what we wanted for a 4 night get away.
Stayed 4 nights in Feb 2025

10/10 Excellent

Adele

Stayed 2 nights in Feb 2025

10/10 Excellent

Kevin

Stayed 1 night in Feb 2025

10/10 Excellent

Anita

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very convenient place and rooms very clean and inviting. Nice to have a bar attached. I would ensure room you get in not near nightclub next door if you want an early night.
Stayed 1 night in Feb 2025

8/10 Good

Judy, Apex

Travelled with family, Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
We liked the music each day on the property and the sitting area in front of the office. We could sit and talk without being directly in front of the music/Bar area. The breakfast was basic, not much for non-carb eaters. Also, unfortunately, only had non-dairy creamers which are full of chemicals. There is milk available, just hated opening a whole carton for a small amount. Towels were soft and thick. One bed was comfortable, the other squeaked and was worn. Bathroom sink was very small, hard to wash your face and no where to set toiletries. No shelf at all in shower, have to place soap and shampoo on the floor. Very hard for a senior person and just plain annoying. Over all a good motel, a little pricey but similar to others in area. We recommend staying here if you don't mind the small annoyances.
Stayed 4 nights in Feb 2025

8/10 Good

Mary

Travelled with family
Liked: Cleanliness, staff & service, amenities
The location was perfect close to the ocean and Duval Street. The motel has character and is tastefully arranged on the outside. The front seating area and live music was wonderful. It was nice to be able to rent bicycles right at the mote. The staff was wonderful. For the price - the room could have been in a little better shape. It was very small, and the towel racks were falling off the wall.
Stayed 4 nights in Feb 2025

10/10 Excellent

chester

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

Great location with great staff.

Check in was quick and painless. Staff was friendly and helpful. Rooms are clean and comfortable. Thanks for the hospitality. Location is perfect, 2 blocks from southern most point and 1 mile to sloppy Joe’s. Never had to drive anywhere.
Stayed 2 nights in Feb 2025

8/10 Good

Verified traveller

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

Decent place with good location

Good location about 15 minute walk to busy Duval bars. Close to Southermost point. Bed comfortable, not many drawers, had to live out of our bags. Nice having a bar in front of hotel.
Stayed 3 nights in Feb 2025

10/10 Excellent

Edward Scott

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Feb 2025

10/10 Excellent

Jodi

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location, location, location! We were very well pleased with everything. The staff was super friendly and helpful!!! Rooms were very clean, and the place had all the amenities we could ask for! Definitely will stay there again and highly recommend SouthWinds to others.
Stayed 4 nights in Feb 2025

8/10 Good

Nikki

Travelled with group
Great place!!!!!
Stayed 2 nights in Feb 2025

10/10 Excellent

ROBERT

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

Southwinds Key West

Easy check in and friendly, attentive staff. Older motel but very clean and great location.
Stayed 2 nights in Feb 2025

10/10 Excellent

Jody

Liked: Cleanliness, staff & service, property conditions & facilities
I cannot say enough good things about this motel. Karen, at the front desk was so helpful. She gave us tons of recommendations and was very accomodating. We parked our car and didn't have to move it until we left Key West. We walked to the beach, Southernmost Point, Bars, Restaurants, Hemingway House and Mallory Square. We would definitely stay here again.
Stayed 2 nights in Feb 2025

8/10 Good

Michael

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice property, pricing is moderate, close to Duval, walkable from Mallory Square to the Southern Most Point. Will stay again!
Stayed 2 nights in Feb 2025

4/10 Poor

Howard

While the staff was generally very good, the noise at night from the accompanying bar with live music made sleep next to impossible until quite late at night. Given that sleep is the main thing you want at this place, it makes it very difficult to endorse it
Stayed 2 nights in Feb 2025

8/10 Good

Kristen

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

Decent value, clean.

Helpful staff, simple but clean renovated rooms, teensy bathroom and no bathroom fan so we must open windows (in full view of passersby). Parking is tight w lg vehicle. Nice outdoor touches (tables and chairs w greenery, hammocks) great little outdoor bar w live music nightly. All in all, good experience. Walkable to all.
Stayed 2 nights in Feb 2025