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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

Bar (on property)
Standard Room, 2 Queen Beds
Property grounds
Front of property
Reception

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Air-conditioning
  • Bar
The current price is AU$598
includes taxes & fees
3 Feb - 4 Feb

Explore the area

View 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.)
    ‪7 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down duvets, pillow-top beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(100 reviews)

Highlights

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

Highlights

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

View all photos for Deluxe Room

Premium bedding, down duvets, pillow-top beds, individually decorated

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
Down duvet
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

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
(107 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Free cots/infant beds
Fridge
LED TV
Renovated in 2016
Pillow-top bed
  • 28 sq m
  • Sleeps 3
  • 1 King 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 self 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
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km

Getting around

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

Restaurants

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Southernmost Point Bar in the USA - ‬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. For a fee, parking is available.

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.

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Property amenities

Parking and transport

  • Parking on site (USD 22.50 per day)
  • Limited on-site self parking

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
  • High chair
  • In-room cot
  • 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 lift

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
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • 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 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

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

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Self-parking fee: USD 22.50 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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

  • 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 27 Jan 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on 3 Feb 2026 start from AU$548.99, 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?

Yep, Southwinds Motel has a self car park for USD 22.50 per day. A self car park is also available, for a fee.

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. 735 out of 1277 reviews
Rating 8 - Good. 333 out of 1277 reviews
Rating 6 - Okay. 136 out of 1277 reviews
Rating 4 - Poor. 52 out of 1277 reviews
Rating 2 - Terrible. 21 out of 1277 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

Reviews

10/10 Excellent

Cristy

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A true hidden gem in Old Town - very clean, comfortable rooms, staff was wonderful!
Stayed 5 nights in Oct 2025

8/10 Good

Crystal

Travelled with partner
Liked: Cleanliness, amenities, property conditions & facilities
We loved our stay here. The room was clean, the staff very friendly and helpful. We loved the bar out front and the live music. And the close proximity to the beach. The pool was nice. Great location to everything we walked alot and also took an uber. Would have liked another luggage stand or somewhere for our clothes but, we knew coming that the room didn't come with dressers or a closet. We will definitely come stay here again.
Stayed 6 nights in Oct 2025

10/10 Excellent

Raquel

Travelled with partner
Liked: Staff & service, amenities, property conditions & facilities
I loved that you could get a daily pass to the beach for towels and chairs, they had laundry(free of charge) onsite that included the soap.
Stayed 6 nights in Oct 2025

10/10 Excellent

Liena

Liked: Cleanliness, staff & service, property conditions & facilities
It was a good stance, we reserved 3 rooms and were clean (as clean as possible)and the staff hepful. We recomend this motel if you plan a gateway based in to know the town since is not the updated place, however it was a nice sorprais, we would stay there again if come back to key kest.!!
Stayed 1 night in Oct 2025

10/10 Excellent

Catherine

Travelled with family
Liked: Cleanliness, staff & service, amenities
Location, location, location! The place looked questionable from the outside, but the service was great and the room was great!
Stayed 2 nights in May 2025

6/10 Okay

Barry

Liked: Cleanliness
Disliked: Staff & service
Tiny rooms. Tiny TV. The bathroom is so small you can’t even close the door while sitting on the toilet. The breakfast was just a counter with some packaged muffins, yogurt packs, packaged eggs.
Stayed 3 nights in Oct 2025

8/10 Good

Bonnie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
There was an issue with the location and facilities of the room but they were resolved with no extra effort
Stayed 4 nights in Oct 2025

8/10 Good

Nancy, Winfield

Travelled with partner
Good location and comfortable enough for the price. We did not realize there is a $25 daily resort fee so be aware. Not sure what for as bike rentals are extra. Guess maybe just for use of the pools?
Stayed 6 nights in Oct 2025

10/10 Excellent

David

Travelled with partner
We loved the island vibe of this older establishment. Everyone on the staff was pleasant, helpful, and great! On the Duval bus loop, but the entire area is an easy walk away. We had the pool to ourselves over half the time. Thank you!
Stayed 6 nights in Oct 2025

10/10 Excellent

Susan

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I stayed 2 nights on the property. Room was large and clean. The bathroom was small but clean. Pool was great after walking around all day. Parking was a little tight but we were so close to Duval St., we never used our car while on the island. We did rent scooters for the day which I would highly recommend to explore more of the island. Hotel does rent bikes and scooters as well.
Stayed 2 nights in Oct 2025

8/10 Good

Joanna

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Oct 2025

10/10 Excellent

Renee

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was great! Friendly, helpful and doing what they could to make our stay even better.
Stayed 4 nights in Oct 2025

8/10 Good

ROBIN

Liked: Cleanliness, staff & service, property conditions & facilities
Property was safe no issues. Room was clean and comfortable.
Stayed 3 nights in Oct 2025

8/10 Good

Don

Stayed 7 nights in Oct 2025

10/10 Excellent

Perry

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

Location. Location. Location!

Perfect location for everything in Key West.
Stayed 2 nights in Oct 2025

10/10 Excellent

Kathy

Travelled with partner
Liked: Amenities
Very safe
Stayed 3 nights in Oct 2025

8/10 Good

Marlene

Liked: Cleanliness, staff & service, room comfort
Pool area was ok, nothing special
Stayed 4 nights in Oct 2025

10/10 Excellent

Nicole

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great place!! Centrally located to be able to walk all over and check out the Duval Street area. Suited our needs perfectly.
Stayed 3 nights in Oct 2025

8/10 Good

Eileen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Bathroom was extremely small, a little outdated. But was clean and quiet! Staff was friendly!
Stayed 2 nights in Oct 2025

10/10 Excellent

Jennie

Travelled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great little motel, staff is great & clean rooms. The bar next door is so convenient
Stayed 6 nights in Oct 2025

8/10 Good

SUSAN, Pella

Travelled with family
Disliked: Property conditions & facilities
Pool area was very small and dated.
Stayed 1 night in Oct 2025

10/10 Excellent

Terry

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
We had an amazing 5 night stay. Tipsy Rooster bar is awesome as well.
Stayed 5 nights in Oct 2025

10/10 Excellent

David

Stayed 2 nights in Oct 2025

10/10 Excellent

John, West Wyoming

Travelled with group
Liked: Amenities
For the money, the motel was acceptable reasonable clean place to lay your head at night. You’re not spending time in your room. The only issue I found was the air conditioner kicking on and off every 15 minutes.
Stayed 3 nights in Oct 2025

8/10 Good

Floyd

Stayed 2 nights in Sep 2025