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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 modern kitchen with a granite countertop, white cabinetry, and a coffee machine.
A white decorative sculpture in a garden area with a white fence and a building in the background.
A modern kitchen with a coffee station, a television, and a display case with baked goods.
A motel with a porch, white chairs, and a signboard.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar
The current price is $171
$152 nightly
$171 total
Total with taxes and fees
Sep 7 - Sep 8

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
(116 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
(92 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
(134 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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Total with taxes and fees
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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
  • 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

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

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. 745 out of 1377 reviews
Rating 8 - Good. 377 out of 1377 reviews
Rating 6 - Okay. 164 out of 1377 reviews
Rating 4 - Poor. 59 out of 1377 reviews
Rating 2 - Terrible. 32 out of 1377 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

Mark

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

Erin

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

10/10 Excellent

Debi

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

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

8/10 Good

Kamryn

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

Dakota

Liked: Cleanliness, amenities, property conditions & facilities
Pool was nice. Breakfast was minimalist but good. Location is great
Stayed 4 nights in May 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

Jerry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice hotel way cheaper than others nearby in Key West. We were near the bar behind the hotel and it was quite loud until about 11 pm, but other than that I am satisfied and would stay here again.
Stayed 1 night in May 2026
Verified review

8/10 Good

Dale

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

10/10 Excellent

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice place to stay. The breakfast was good, pools were nicely kept very clean and always towels available. The best part was the use of the beach, great chairs and towels provided. The area was very quiet and comfortable
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Theresa

Liked: Cleanliness, staff & service, property conditions & facilities
Conveniently located, basic hotel was decent for the price. Staff help us rent scooters.
Stayed 2 nights in May 2026
Verified review

8/10 Good

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small, clean & tidy room. Good location for walking around. Little bar next door had great live music.
Stayed 2 nights in May 2026
Verified review

8/10 Good

Rebecca

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This hotel is very well located, close to the beach and southernmost point. It is an older property so not a lot of amenities, the staff was friendly and there was a small complimentary breakfast.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Roxie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a problem with the reservation but the staff was very efficient with fixing it and put our minds at ease. Our stay here was everything thing we needed. I love the nostalgia of the place.
Stayed 4 nights in May 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

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Basic ROOM but FANASTIC location
Stayed 2 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

10/10 Excellent

Kimberly

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

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

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