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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
Exterior
2 outdoor pools, pool umbrellas, pool loungers
Standard Room, 2 Queen Beds
Reception

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Air conditioning
The current price is NZ$306
includes taxes & fees
26 June - 27 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

8.4 out of 10
Very good
(96 reviews)

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

10.0 out of 10
Exceptional
(7 reviews)

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

8.8 out of 10
Excellent
(53 reviews)

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

8.4 out of 10
Very good
(83 reviews)

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 24 Jun 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on 26 Jun 2025 start from NZ$258.75, 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. 638 out of 1113 reviews
Rating 8 - Good. 292 out of 1113 reviews
Rating 6 - Okay. 122 out of 1113 reviews
Rating 4 - Poor. 43 out of 1113 reviews
Rating 2 - Terrible. 18 out of 1113 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

8/10 Good

Kimberly

Travelled with family, Travelled with group
Liked: Staff & service, amenities
Staff was great and very helpful. They will book excursions, take care of golf cart rentals and have bike rentals onsite. Roosters, the bar attached to the motel was perfect with music every night. The rooms are small, especially the bathroom but fine for a few nights. I'm not sure I could stay here long term, but again, perfect for a short stay.
Stayed 3 nights in Mar 2025

6/10 Okay

Ian

Liked: Cleanliness
Disliked: Property conditions & facilities

Overpriced old school motel, shabby but clean.

This would be a $150 a night place anywhere else. 3x as much in Key West. It's a typical old school motel. Showing its age a lot. It was clean and has a great location. The biggest annoyance was it has a functioning kitchen but not a single spec of any pots, silverware or anything at all. I had to forage in the breakfast room to find a few plates and plastic silverware.
Stayed 3 nights in Mar 2025

8/10 Good

Elke

Liked: Cleanliness, staff & service
Downtown sehr gut mit Shuttlebus erreichbar.
Stayed 1 night in Mar 2025

10/10 Excellent

Keri

Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Just a walk away from everything! Nice rooms, just a little dated. No utensils or dishes in kitchen. Otherwise great staff, very kind & helpful. Great continental breakfast. 2 pools, great for families! Free laundry on site!
Stayed 2 nights in Mar 2025

10/10 Excellent

Kimberly, Huntington Beach

Liked: Cleanliness, staff & service, property conditions & facilities
Quant property in the heart of ‘Southermost’ away from the high traffic touristy areas. I loved that it had a bar, nightly live music, dessert truck & 2 pools on site with multiple beaches, food options & Trolley stop 11 within a few blocks.
Stayed 3 nights in Mar 2025

8/10 Good

Kathryn

Travelled with family
Liked: Amenities
Continental breakfast and great location. Rooms were dated but clean
Stayed 1 night in Mar 2025

10/10 Excellent

Mary

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

Pleased traveling coupe!

Even though the room is small, the cleanliness, service and comfort were exceptional!! The staff was soooo helpful!!!
Stayed 1 night in Mar 2025

10/10 Excellent

Doug

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

10/10 Excellent

Heather

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect little motel
Stayed 1 night in Mar 2025

8/10 Good

ronald

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location
Stayed 4 nights in Mar 2025

6/10 Okay

Veronica

Travelled with family

Perfect for the night

I book three rooms for a group of 2 adults with 6 teenagers. Its not a fancy place but certainly a comfortable one. Its close to everything just 20 min walk from the boat docks. Live music and entertainment, bar, snack mobile, Hammocks, scooter rentals all you can possibly needs for a short fun stay. Just 2 blocks from the famous Key West buoy. Front desk service was kind and efficient. Will stay here again.
Stayed 1 night in Mar 2025

10/10 Excellent

Doug

Stayed 2 nights in Mar 2025

10/10 Excellent

Bruce

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love staying here!!! The staff is always amazing and the rooms are nice and clean. Parking outside your room is a bonus. Convenient walk to beaches, bars and dining.
Stayed 1 night in Mar 2025

6/10 Okay

Nikhil

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Nov 2024

10/10 Excellent

Kerry

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I am a repeat customer and will come back again!
Stayed 2 nights in Mar 2025

8/10 Good

Marilyn

Stayed 3 nights in Mar 2025

6/10 Okay

Karen

Liked: Staff & service, property conditions & facilities
Stayed 3 nights in Mar 2025

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