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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

2 outdoor pools, pool umbrellas, pool loungers
Front of property
Deluxe Room | Terrace/patio
Standard Room, 1 King Bed | Premium bedding, down duvets, pillow-top beds, individually decorated
Reception

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 duvets, pillow-top beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(100 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down duvets, pillow-top beds, individually decorated

Standard Room, 2 Queen Beds

8.6 out of 10
Excellent
(74 reviews)
  • 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)
  • 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 | Premium bedding, down duvets, pillow-top beds, individually decorated

Standard Room, 1 King Bed

8.4 out of 10
Very good
(108 reviews)
  • 28 sq m
  • Sleeps 3
  • 1 King Bed

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includes taxes & fees
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About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach
2 outdoor pools, a bar/lounge and self parking are available at this hotel. Continental breakfast is free. Other amenities include coffee/tea in a common area, concierge services and laundry facilities. Housekeeping is available on request.
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.

2 outdoor swimming pools are on site.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Our customers tell us that they enjoy the free breakfast at Southwinds Motel. During your stay, you're just a quick walk from Duval Street. Enjoy features like 2 outdoor pools, a bar and concierge services.
  • Free continental breakfast served daily
  • Enjoy drinks at the bar/lounge
  • Self-parking available for a fee
  • Take a swim in the 2 outdoor pools
  • Services include a concierge, tour or ticket assistance and luggage storage
  • Guests really like the accommodation for the comfy beds and cleanliness
  • Steps from South Beach and 3 minutes on foot from Duval Street
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.

Guests are served a free continental breakfast daily from 7:00 AM to 10:00 AM.
Tipsy Rooster – This bar only serves light fare.

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

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 at the property

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Front desk staff will greet guests on arrival at the property.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

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

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

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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled with family, Travelled with partner, Travelled with group
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

Travelled 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

Travelled 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

Travelled 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

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

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