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Southwinds Motel

2.0 star property
Hotel near Duval Street in Key West

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Photo gallery for Southwinds Motel

2 outdoor pools, pool umbrellas, sun loungers
Deluxe Room | Terrace/patio
Front of property
Reception
Standard Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, individually decorated

Reviews

8.8 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.)
    ‪11 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
(100 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

8.6 out of 10
Excellent
(74 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
(108 reviews)
  • 300 sq ft
  • Sleeps 3
  • 1 King Bed

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About the neighborhood

Key West

Old Town Key West stay.A stay at this Old Town Key West hotel places you steps from South Beach and within a 5-minute walk of Duval Street. Southernmost Point and Ernest Hemingway Home and Museum are also within half a mile (1 km).

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

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Banana Cafe - ‬4 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk

About this property

Southwinds Motel

Hotel near Duval Street in Key West
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 is 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 feature coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Pillowtop beds feature down comforters and premium bedding. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include showers and complimentary toiletries.

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

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Property amenities

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room crib
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate

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

Things to do

  • 2 outdoor pools

Accessibility

  • No elevator

Room amenities

Entertainment

  • 32-inch LED TV with cable channels

Bedroom

  • Down comforter
  • Free crib
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

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

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Free cribs (infant beds)!

Property 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 guestroom 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 each 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

How close is Southwinds Motel to the airport?

Southwinds Motel is 3.2 mi (8-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

How much does it cost to stay at Southwinds Motel?

As of Feb 13, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Feb 16, 2026 start from $372.49, excluding 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.

Does Southwinds Motel have an airport shuttle?

Airport shuttle services are not available at Southwinds Motel.

How close is Southwinds Motel to the beach?

This hotel is a short 3-minute walk from South Beach and 11-minute walk from Clarence S. Higgs Memorial Beach Park. Don't forget your sunscreen!

Does Southwinds Motel offer free breakfast?

Southwinds Motel offers free continental breakfast every day from 7:00 AM to 10:00 AM.

Is there a casino at Southwinds Motel?

No, there is no casino at this hotel.

What time is check-in at Southwinds Motel?

Check-in start time: 4:00 PM; Check-in end time: midnight.

Is there free parking at Southwinds Motel?

Free parking is not available at this hotel. Self parking is available for USD 22.50 per day.

Does Southwinds Motel have a pool?

Southwinds Motel features 2 outdoor pools.

Does Southwinds Motel have a restaurant?

Southwinds Motel is home to Tipsy Rooster, which features light fare.

Does Southwinds Motel have a spa?

There are no spa services available at this hotel.

How close is Southwinds Motel to downtown Key West?

Southwinds Motel is 0.6 mi away from Key West.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 736 out of 1286 reviews
Rating 8 - Good. 334 out of 1286 reviews
Rating 6 - Okay. 141 out of 1286 reviews
Rating 4 - Poor. 54 out of 1286 reviews
Rating 2 - Terrible. 21 out of 1286 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

4/10 Poor

Thomas, Warwick

Put us in a room right next to bar that had extremely loud music till 1-2 AM, also outside lights on all night and it was like daytime in the room, even with blinds closed, no drapes, made reservations for 2 rooms months earlier and our friends were the farthest room away from us
Stayed 2 nights in Dec 2025

8/10 Good

Robert

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Nice motel traditional Key West building in a great position for downtown. Room was clean nice beds bathroom is very dated but clean. Staff were excellent.
Stayed 4 nights in Nov 2025

6/10 Okay

Linda

Liked: Cleanliness, staff & service
Room is very small with nowhere to put things. However it was clean. Excellent location for walking all around key West. Breakfast was small.
Stayed 2 nights in Nov 2025

8/10 Good

Dorothy, philadelphia

Liked: Cleanliness, amenities
Disliked: Property conditions & facilities
The place is Old. It was clean. You will find rust, chips in the floors, water pressure in the shower(room 33) very bad. The price & location Great. The small pool, was never useable for the 7 nights we were there. It was Green & cold. The continental breakfast & parking are worth it alone. I would stay there again. I visit Key West one or two times a year.
Stayed 7 nights in Nov 2025

10/10 Excellent

Carla, Monroeville

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Location was exactly what we were looking for. Close enough to walk to everything yet away from the noise and bars of Duval street. Great room, staff and amenities. Pool was nice, clean and water temp was perfect. Definitely staying here again.
Stayed 4 nights in Oct 2025

10/10 Excellent

Mary

Traveled with group
Liked: Cleanliness, staff & service, amenities
Roomwas clean! Great location
Stayed 2 nights in Nov 2025

8/10 Good

Tara

Liked: Cleanliness, staff & service
We love our stay at Southwinds. There are a couple things that could make it much better: 1. Some hooks on the shower door or bathroom wall for towels. 2. A bit more water pressure or a new shower head. Other than that - it's always a pleasure staying at Southwinds. We love the location. It's quiet. It's in walking distance to many of the locations we love. The Tipsy Rooster is a great bonus also. The beds are comfortable. The AC works great. The pools are amazing.
Stayed 5 nights in Nov 2025

10/10 Excellent

Shane

Stayed 4 nights in Nov 2025

10/10 Excellent

Jeanne

Traveled with group
Liked: Cleanliness, amenities, property conditions & facilities
Everything about this place was perfect!
Stayed 4 nights in Nov 2025

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, amenities
Keep in mind it’s a motel! Staff were very friendly and the place was clean, as was the bathroom. Never entertained the two pools they have but people seemed to enjoy them. I think my only don’t is the property owns a bar next door and if your room is next to it - it can be quite noisy. Otherwise if ya not looking for all the fancy frills go for it, I’d stay again. They accommodate parking too, we rented a golf cart and it was no problem parking on the property. Enjoy!
Stayed 3 nights in Oct 2025

10/10 Excellent

Laura E

Stayed 2 nights in Nov 2025

10/10 Excellent

Michelle

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Quaint motel in a great location. Everything is in walking distance. Motel is older but clean. Check in was easy and the employees were really nice. Breakfast was sufficient, tied us over until lunch. We had a total of 4 rooms. Ours was small but we don’t spend much time in there so it was fine. Our only issue was how loud the air conditioner was when it clicked on, yikes. We would all come back again. Definitely recommend staying here.
Stayed 2 nights in Nov 2025

8/10 Good

Jose

Traveled with group, Traveled with partner, Traveled with family
Liked: Property conditions & facilities
Staff was very courteous.
Stayed 6 nights in Oct 2025

10/10 Excellent

Linda

Liked: Cleanliness, amenities, property conditions & facilities
Location, location, location! And it is darling! Check in was so helpful, like a tourist guide!
Stayed 2 nights in Nov 2025

10/10 Excellent

Matthew

Stayed 4 nights in Oct 2025

8/10 Good

Alfred

Liked: Staff & service
Stayed 4 nights in Oct 2025

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities
Great
Stayed 6 nights in Oct 2025

10/10 Excellent

YUBER, Bronx

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
very convenient to all locations and clean quite rooms.
Stayed 5 nights in Oct 2025

8/10 Good

Shantel

Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
The room wasn't spotless but was still clean. The inside of draws could be vaccumed or wiped down more. Staff was courteous. Heated pool wasn't so heated as they said. For the Queen bedroom, the bathroom toiletries wasn't much as far as soap and shampoo.
Stayed 5 nights in Oct 2025

10/10 Excellent

David Anthony

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
The room was excellent, staff were very nice and helpful. The breakfast was very nice. The pool was perfect. The bar outfront with live music ( nightly) was great. The Ice cream shop next door had wonderful ice-cream combinations and donut combinations.
Stayed 6 nights in Oct 2025

10/10 Excellent

Darlene

Stayed 1 night in Oct 2025

10/10 Excellent

Kevin

Liked: Cleanliness, staff & service, amenities
Nightly entertainment at the tipsy rooster was a huge treat! Check in was fast and easy! Clean cool room. Great location to the beach!
Stayed 3 nights in Oct 2025

10/10 Excellent

Alan

Stayed 2 nights in Sep 2025

10/10 Excellent

Michael

Liked: Cleanliness, amenities, property conditions & facilities
grerat room at a great price
Stayed 1 night in Oct 2025

10/10 Excellent

Cristy

Traveled 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