Southwinds Motel

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

Photo gallery for Southwinds Motel

Exterior
2 outdoor pools, pool umbrellas, pool loungers
Property grounds
Reception
Exterior

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry
  • Pool
  • Air conditioning
The current price is NZ$271
includes taxes & fees
17 Aug - 18 Aug

Explore the area

View 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

Standard Room, 1 King Bed

8.4 out of 10
Very good
(101 reviews)

Highlights

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

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Down duvet
Sofa bed
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(65 reviews)

Highlights

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

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(88 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Separate bedroom
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

  • ‪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
  • Seaside Cafe at the Mansion

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

Similar properties

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 15 Aug 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on 17 Aug 2025 start from NZ$223.76, 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. 668 out of 1155 reviews
Rating 8 - Good. 293 out of 1155 reviews
Rating 6 - Okay. 128 out of 1155 reviews
Rating 4 - Poor. 49 out of 1155 reviews
Rating 2 - Terrible. 17 out of 1155 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

6/10 Okay

Hallie

Travelled with group
Liked: Cleanliness
Disliked: Staff & service
The workers were quite literally the only damper. We were told we would have housekeeping come every 3 days. When the 3rd day came, we put our towels out on the floor to be picked up. When we came back the room was still not cleaned and dirty towels still there. Went to desk the next day to ask about housekeeping and when we told them they never came they said “that’s not good.” Oh? So then we asked for towels so we could at least shower. We were told no housekeeping was on the way. After 30 min we called and were told housekeeping was coming. Housekeeping came and we were kicked out of our room so they could clean, again all the while we were waiting all we wanted was clean towels so we could shower and leave for the day. When I asked for again shower towels days later I was given a beach pass? I asked “how does this get us shower towels?” Then the worker laughed and said she blunt I said “beach pass” ok idk how you get beach pass from shower towels but ok. Maybe look into retraining people who don’t know left from right.
Stayed 8 nights in Apr 2025

8/10 Good

Penni

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice
Stayed 1 night in May 2025

10/10 Excellent

Tammy A

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Close to beach
Stayed 4 nights in Apr 2025

10/10 Excellent

Keith

Liked: Cleanliness, staff & service, property conditions & facilities
Location The motel is well situated only a block away from a small sandy beach and a couple of blocks away from the "southern most point", in downtown Key West. There is a free hop on hop off "Duval loop" bus service that runs every 30 minutes or so. Motel It reminds me of something out the 1950's, (in a good way) but with up to date additions like WiFi etc. The room we had was small but perfectly presented. Check-in was smooth and staff were lovely. Package came with breakfast, which was nice with a good selection & kept restocked. The pool was in good order with free pool towels. There are a number of places to eat around and about (our best find for a quick bite was a catering truck right opposite the motel, good size burger & fries for not much money)
Stayed 2 nights in May 2025

10/10 Excellent

Renee

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was exactly the old Florida feel I was looking for and delivered on quaintness and retro excellence. For the age of the property it was very well maintained and clean. The rooms were large and I loved the mini fridge and microwave. The staff were incredibly friendly and the location could not be beat. Everything I was hoping it would be and more
Stayed 1 night in May 2025

10/10 Excellent

Milinda

Business traveller, Travelled with family, Travelled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 5 nights in May 2025

10/10 Excellent

Kathy

Travelled with partner
Liked: Cleanliness, amenities
Awesome!
Stayed 4 nights in Apr 2025

8/10 Good

Steven

Liked: Cleanliness, staff & service, room comfort

Anniversary Trip 2025

The Southwinds Motel was a wonderful place to stay. I would highly recommend staying there for a nice couples retreat away. The service was wonderful and location perfect!
Stayed 4 nights in Apr 2025

10/10 Excellent

Donna, Lafayette

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Apr 2025

8/10 Good

Russell

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Friendly staff and loved having the Tipsy Rooster there. Enjoyed the music very much.
Stayed 5 nights in Apr 2025

10/10 Excellent

MICHAEL

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in May 2025

10/10 Excellent

Sara Irma

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
From the moment we checked in, meeting the front desk staff, they were friendly, gave us information to make our stay comfortable and worry free. Our room was towards the back, quiet, clean and parking right in front. We loved that parking is free. Another plus, besides a big coffee pot in the room, in the morning, grab and go continental breakfast in the lobby was very nice and convenient. Definitely would stay here again and I would recommend to other travelers.
Stayed 2 nights in Apr 2025

10/10 Excellent

Justin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Place was awesome.
Stayed 1 night in Apr 2025

10/10 Excellent

Marilyn

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

Good except the bathroom light was a little bright

Stayed 2 nights in Apr 2025

10/10 Excellent

Sarah

Liked: Cleanliness
Stayed 3 nights in Apr 2025

10/10 Excellent

Peter

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A hop and a skip to the Tipsy Rooster
Stayed 2 nights in Apr 2025

10/10 Excellent

laura

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Apr 2025

8/10 Good

Pamela

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I liked the "old Florida" feel of Southwinds. The staff was friendly and helpful. I loved having the option of the pools or the beach (with beach chairs and towels). It was a great location-close to cafes, the Tipsy Rooster (with daily live music) and the free Duval Loop Bus stop. While the bed was very comfortable, the other furniture in the room (dresser, table, chairs) was dated. Would definitely come back!
Stayed 6 nights in Apr 2025

10/10 Excellent

Barbara

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was close to everything and quiet, nice outdoor seating areas, parked our car in a safe area and walked everywhere in town
Stayed 2 nights in Apr 2025

6/10 Okay

Rognvald

Travelled with family
Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service
Perfect location. Good value & clean. Most staff very good, but Karen on the Front Desk was rude & unprofessional when I was trying to address the return of my security deposit.
Stayed 2 nights in Feb 2025

8/10 Good

Tarabeth

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was a bit small, but it suited our needs for the long weekend trip to Key West.
Stayed 3 nights in Apr 2025

10/10 Excellent

Annmarie

Travelled with family, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such nice staff! Great area! Everything you need is a short walk away. Includes access to a beach with chairs and towels too!
Stayed 1 night in Apr 2025

10/10 Excellent

Annmarie

Travelled with family, Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was incredibly kind and helpful! Especially with my handicap mother. Shout out to Nico and Quiana! They were wonderful! This was the least expensive motel I could find for our large group and I was nervous about the quality. While some of the rooms are very small, ours was large and comfortable. I had no reason to worry! They have 2 nice pools, clean rooms and coffee ready in the morning. It's a very walkable area. They also have parking for cars or golf carts. Close to so many things! I was very happy with everything!
Stayed 4 nights in Apr 2025

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Apr 2025

4/10 Poor

Brian

Travelled with family
Disliked: Cleanliness, amenities, property conditions & facilities
At the driveway, the trees/shrubs knocked off our sideview mirror. That will be $1,700 repair cost on top of the cost of motel - damage caused by this property. Of course the next day, the bushes/tree had been cut down !! No offer by property to help our repair costs !
Stayed 3 nights in Apr 2025