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Southwinds Motel

Property class: 2

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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 motel with a porch, white chairs, and a signboard.
A white decorative sculpture in a garden area with a white fence and a building in the background.
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
  • Parking available
  • Bar
The current price is $190
$169 nightly
$190 total
Total with taxes and fees
Oct 26 - Oct 27

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
(117 reviews)
  • 250 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

A hotel room with two beds, a TV, and a window with blinds.

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(95 reviews)
  • 400 sq ft
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

A hotel room with a bed, a bedside table with a lamp, a coffee maker, and a window with blinds.

Deluxe Room

10.0 out of 10
Exceptional
(8 reviews)
  • 300 sq ft
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

A hotel room with a large bed, a TV mounted on the wall, a small table with chairs, and a window with curtains.

Standard Room, 1 King Bed

8.4 out of 10
Very good
(135 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Key West

With a stay at Southwinds Motel in Key West (Old Town Key West), you'll be steps from South Beach and 3 minutes by foot from Duval Street. .This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.

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

  • ‪Circle K - ‬6 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬5 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

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.

Make yourself at home in one of the 58 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with down comforters and premium bedding. 32-inch LED televisions are provided, with cable programming available. Private bathrooms with showers feature complimentary toiletries and hair dryers.
Make use of convenient amenities such as concierge services, a picnic area, and a vending machine.
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:00 AM to 10:00 AM.
Featured amenities include complimentary newspapers in the lobby, a 24-hour front desk, and multilingual staff. Self parking (subject to charges) is available onsite.
A complimentary continental breakfast is served each morning between 7:00 AM and 10:00 AM.
Tipsy Rooster - This bar serves light fare only. Open daily.

Property amenities

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

Restaurants on site

  • Tipsy Rooster

Things to do

  • 2 outdoor pools

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room crib
  • 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 elevator

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free crib
  • 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
  • Individually decorated
  • Individually furnished
  • 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

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Free cribs are available on request at the property

Property payment types

  • American Express
  • Diners Club
  • Discover
  • Mastercard
  • Visa

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • 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 have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 22.50 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

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

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms
Alcohol is not served at this property

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. 754 out of 1387 reviews
Rating 8 - Good. 374 out of 1387 reviews
Rating 6 - Okay. 167 out of 1387 reviews
Rating 4 - Poor. 59 out of 1387 reviews
Rating 2 - Terrible. 33 out of 1387 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice little property, and great location!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location good place to stay!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent staff and a fun place to stay.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
great location!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay! The staff was awesome!
Stayed 3 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good place, clean and quiet.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A beautiful Key West Motel! Will definitely stay there again!
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was fantastic!!
Stayed 7 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very good location! Cute older place it was clean and nice. Great grab and go breakfast.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Place was close to everything
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We spent a long weekend at this hotel for my birthday. The room was nice and cold and the location was great. We especially liked the bar next-door and the Cuban restaurant across the street.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a good stay. Close to the ocean and restaurants.
Stayed 3 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay because you are close to everything. Walls are thin so it can get loud. Good breakfast, great pool and super helpful staff.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Adorable motel with a continental breakfast, two pools and a short walk to the beach. I would stay here again.
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

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

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great overall!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was what you would expect as an old schooler motor lodge. Great location to get to South Beach as well as down Duval street to all the stores, restaurants and bars. Great bar with some goo live musics right there on location with a liquor store to boot.
Stayed 4 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very courteous and helpful. Our room was very clean and comfortable. A good, fresh variety of items, along with coffee. milk, and juices were available for breakfast.
Stayed 1 night in Jul 2026
Verified review

8/10 Good

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

10/10 Excellent

Liked: Cleanliness, staff & service, amenities
Clean and cozy pool area.
Stayed 2 nights in Jun 2026
Verified review

8/10 Good

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

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent Staff bicycle rental on-site
Stayed 5 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was close to everything
Stayed 3 nights in Jun 2026