Southwinds Motel, Key West

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From153US$ /night
Check-in
24Feb2026Select date
Check-out
25Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

1321 Simonton Street, Key West, Florida, United States, 33040
Very good
7.9
8.6
/10
3.8
/5

Experience the charm of Southwinds Motel, a 2-star Key West hotel rated 8.0/10 on Booking.com. This property features two outdoor pools, complimentary WiFi, and easy beach access. Ideal for various travelers, it is just steps away from restaurants and local attractions.

Rooms & Amenities

Accommodations at Southwinds Motel include clean and modern rooms featuring Eurotop mattresses, microwaves, refrigerators, and 32-inch flat-screen TVs. Guests can choose from various room types, including standard queen beds and family-friendly options with sofa beds, offering thoughtful amenities for seamless stays.

Dining & Leisure

Guests can start their day with a Continental breakfast and unwind poolside at one of the two outdoor pools. The property also offers complimentary beach access, complete with chairs and towels, enhancing the experience of relaxing under the Florida sun.

Services & Local Area

Southwinds Motel provides guests with convenient bike and scooter rentals for easy exploration of the vibrant surroundings. It is located just a short walk from local favorites such as Louie's Backyard and the Southernmost Point, making it easy to enjoy dining and entertainment.

Attractions & Transportation

The motel is within proximity to attractions such as the Ernest Hemingway Home and Museum and Fort Zachary Taylor State Park. Public transportation options include the Lower Keys Shuttle, with Key West International Airport just a 10-minute drive away.

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Select your room type

Southwinds Motel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Queen Room Two Queen Beds
2 persons
325 sq. feet 
2 King Size Beds
Coffee machine
Air conditioning
Standard King Room
2 persons
205 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
Queen Deluxe
2 persons
500 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
Standard Queen Room
2 persons
205 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
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Facilities

Southwinds Motel offers amenities for your comfortable stay and unforgettable experiences
Facilities: Very good
7.7/10Review score

General

  • Non-smoking rooms
  • Paid Wi-Fi
  • Parking
  • 24-hour reception
  • No pets allowed
  • Luggage storage
  • Vending machines

Services

  • Laundry
  • Tours/Ticket assistance

Dining

  • Bar/ Lounge area

Spa & Leisure

  • Heated swimming pool
  • Outdoor swimming pool
  • Sun loungers

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Patio
  • Garden furniture
  • Ironing facilities

Bathroom

  • Free toiletries

Media

  • Flat-screen TV
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Southwinds Motel Location

1321 Simonton Street, Key West, Florida, United States, 33040
Map view
1321 Simonton Street, Key West, Florida, United States, 33040
Nearby
South Street Corner of South and Whithead Streets
Statue Of Bishop Albert Kee
1000 ft
Gallery
Alan S Maltz Gallery
1500 ft
Gallery
Key West Pottery
1700 ft
Gallery
Island Arts Co-op
1700 ft
Gallery
Frangipani Gallery
2000 ft
Restaurants
Southern Most Deli
500 ft
1330 Simonton St
Southernmost Smoothie Shop
1500 ft
1219 Duval St
The Green Pineapple Cafe
1800 ft
1130 Duval St
Flamingo Crossing
2100 ft
1105 Duval Street
Papa John's
2100 ft
538 Truman Ave
Sinz Burritos
2600 ft
500 Truman Ave Unit 1
Key West Cuban Coffee
2000 ft
517 Truman Ave Key West
Tropical Juices & Drinks
2400 ft
925 Duval St
Viva Saloon
2700 ft
903 Duval St
Dons' Place
2100 ft
1000 Truman Ave
Getting around
City Centre
Key West20 min  ·  1.0 mi
Airports
Key West International Airport (EYW)8 min  ·  3.0 mi
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Property information and rules
Check-in
from 16:00-23:59
Check-out
from 08:00-11:00
Guest Parking
Paid Private parking is possible on site.
Internet
is available in for additional charge.
Breakfast
At the hotel Southwinds Motel guests are invited to a full breakfast served for free. 
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are not allowed.
Languages
English, Spanish, Russian, Latvian
Number of rooms:
58
Former name
Southwind Motel

Reviews and Ratings

Feedback about Southwinds Motel from previous guests about their experience.
Review score
Based on 1277 verified reviews
8.2/10
Great
81%
Recommend
Breakfast
6.0/10
Cleanliness
8.1/10
Comfort
8.1/10
Facilities
7.7/10
Free Wi-Fi
8.5/10
Location
9.2/10
Paid Wi-Fi
7.7/10
Staff
8.7/10
Value for money
7.4/10
Guest reviews
based on 1584 reviews
4.5/5
based on 1824 review
7.9/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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