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Southwinds Motel

2.0 star property

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Photo gallery for Southwinds Motel

An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".
A white decorative sculpture in a garden area with a white fence and a building in the background.
A motel with a porch, white chairs, and a signboard.
A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.
A modern kitchen with a coffee station, a television, and a display case with baked goods.

Reviews

8.6 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.)
    ‪8 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

A hotel room with a bed, a wardrobe, a door, a microwave, and a bathroom with a toilet and towel rack.

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(112 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds

8.6 out of 10
Excellent
(84 reviews)
  • 37 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down duvets, pillow-top beds, iron/ironing board

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

Standard Room, 1 King Bed

8.4 out of 10
Very good
(124 reviews)
  • 28 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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About this property

Southwinds Motel

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 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.

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 they enjoy the free breakfast at Southwinds Motel. During your stay, you're just a quick walk from Florida Keys Beaches. 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 accommodations for the cleanliness and comfy beds
  • Steps from South Beach and 3 minutes by 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 free continental breakfast daily from 7:00 AM to 10:00 AM.
Tipsy Rooster - This bar serves light fare only. Open daily.

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 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)!

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

8.6

Excellent

Rating 10 - Excellent. 740 out of 1362 reviews
Rating 8 - Good. 373 out of 1362 reviews
Rating 6 - Okay. 160 out of 1362 reviews
Rating 4 - Poor. 58 out of 1362 reviews
Rating 2 - Terrible. 31 out of 1362 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

Verified review

8/10 Good

Cheryl

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Was clean Great location The bar was great
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

CONNIE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel, clean and excellent location.
Stayed 2 nights in Mar 2026
Verified review

8/10 Good

Steven

Liked: Cleanliness, staff & service, amenities
Great place - can walk to most activities- place a bit dated - decent breakfast- staff super friendly- would stay again.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Deborah

Liked: Cleanliness, amenities, property conditions & facilities
Great location and comfortable stay.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect location for our family vacation to Key West! Very friendly staff, clean rooms, basic continental breakfast (all pre-packaged).
Stayed 4 nights in Apr 2026
Verified review

8/10 Good

Dale

Liked: Cleanliness, staff & service, property conditions & facilities
Good location.
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

Cynthia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful and helpful staff.
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Wonderful, pleasant and informative staff.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Diana

Liked: Cleanliness, staff & service, property conditions & facilities
Super great location
Stayed 1 night in Mar 2026
Verified review

8/10 Good

Catherine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was good and clean. The staff were nice, and very helpful. I would stay here again. Very affordable.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Jo Ann

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast had a great variety to choise from!
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Kimberly

Wonderful location, had everything we needed!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was very clean and the staff was great. I really enjoyed the heated pool.
Stayed 5 nights in Mar 2026
Verified review

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Walking distance to Duval Street. Love that The Tipsy Rooster bar is right next door! Will definitely stay here again.
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Thomas J

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
always a great time here
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Scott

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
That is our second time staying there and we absolutely enjoy the place. We enjoy the location. It’s quick to walk to. We enjoy the beach access. Everybody is so familiar there. We will be staying there again soon.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

William

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Was as depicted, clean, fun, good price,
Stayed 2 nights in Mar 2026
Verified review

8/10 Good

Rick

Liked: Cleanliness, staff & service, property conditions & facilities
Room was nice staff was nice
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

SALVATORE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was awesome
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

Hailey

Liked: Cleanliness, amenities, property conditions & facilities
Perfect little place, great location!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Ronnie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was great. Breakfast was good too.However there was no place to sit for breakfast.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Jerome

Liked: Cleanliness
All good, classic MOTOR HOTEL!
Stayed 1 night in Apr 2026
Verified review

8/10 Good

Sally

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic location and friendly staff.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Tatiana

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice place to stay, within 30 minute walk to all fun places in old Key West. Very weak water supply during our stay.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Karen

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff
Stayed 4 nights in Jan 2026

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