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Check-in
15Jan2026Select date
Check-out
16Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

1321 Simonton Street, Key West, Florida, United States, 33040
-
Steps from South Beach
Very good
7.9
8.6
/10
3.8
/5

Rooms at Southwinds

Southwinds Motel provides Eurotop mattress beds, complimentary Wi-Fi, a microwave, a refrigerator, and a 32-inch flat-screen cable TV. Each room also includes ironing facilities, heating, air conditioning, a sitting area, a patio, and garden furniture. Free toiletries are available. The Standard Queen features one queen bed. The Queen Room with Sofa Bed includes a seating area with a sofa bed. Standard Two Queen has two queen beds. Standard King includes one king bed. Tea-and coffee-making facilities are available in some rooms.

Dining options

Southwinds Motel provides a complimentary Continental breakfast with muffins, pastries, cereals, oatmeal, yogurts, fresh fruit, milk, coffee, tea, and juices. The Tipsy Rooster specializes in local spirits and hand-crafted cocktails. Guests can also have homemade soft-serve ice cream with freshly made mini-donuts with toppings.

Leisure and Fun

Southwinds Motel has two outdoor pools. Guests have access to the beach with complimentary chairs and towels. Lama Mobility's electric kick scooter rentals are on-site. Renting bikes and scooters are available.

Location and Transport

Southwinds Motel is one block from Duval Street and steps from the Atlantic Ocean. The Southernmost point of the United States is located at the corner of South Street and Whitehead Street in Key West, Florida, steps from Southwinds Motel. USCGC Ingham Maritime Museum is 3 km away. Key West International is 5 km away.

Services at Southwinds

Southwinds Motel provides concierge service. Wi-Fi is complimentary. Laundry and housekeeping are on-site. Parking is complimentary.

“In my opinion, its location near shopping and Duval Street is a definite advantage, especially with bike rentals readily available. The general cleanliness appeared to be a high point for most. I noted that some found the rooms basic, but clean and efficient, making it suitable for travelers focused on exploring Key West rather than spending time in the room.”
Hotel logo
James DavidEditor-in-Chief at Tohotel
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Select your room type

The hotel 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
Standard Queen 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
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Price and Room Availability Calendar

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Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

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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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
Explore Key West
Local Highlights Near Southwinds Motel
Top Attractions
Activities
Dining
Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
11 minutes' walk
The historic residence of Hemingway showcases his writing and features beautiful gardens and cats that roam the grounds.
Duval Street
Duval Street
11 minutes' walk
A vibrant street known for its lively atmosphere, shopping, bars, and restaurants, perfect for experiencing Key West's nightlife.
Southernmost Point
Southernmost Point
11 minutes' walk
Famous buoy marking the southernmost point in the continental US, offering iconic photo opportunities against the ocean backdrop.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
A serene beauty sanctuary filled with butterflies and tropical birds, providing an educational experience in a lush garden setting.
Snorkeling Tours
5 minutes' drive
Exciting snorkeling adventures at nearby coral reefs, with all gear provided. Suitable for all experience levels and seasonal.
Yoga on the Beach
8 minutes' walk
Relaxing yoga classes on the beach, ideal for unwinding. Classes available daily, suitable for all skill levels.
Kayaking at Higgs Beach
6 minutes' walk
Kayak rentals available for exploring the coastal waters, perfect for solo adventurers or families enjoying the sun.
Sunset Celebration at Mallory Square
25 minutes' walk
A lively gathering featuring performers, artisans, and food vendors as the sun sets. Great for all ages to enjoy the local culture.
Southern Most Deli
Southern Most Deli
2 minutes' walk
Charming deli offering fresh sandwiches and breakfast options. Known for its quick service and local flavor.
The Green Pineapple Cafe
The Green Pineapple Cafe
7 minutes' walk
Relaxed atmosphere with health-conscious options. Popular for smoothies, salads, and brunch with vegetarian selections.
Flamingo Crossing
Flamingo Crossing
8 minutes' walk
Casual spot known for seafood and Caribbean cuisine. Offers outdoor seating and a friendly vibe.
Papa John's
Papa John's
8 minutes' walk
Popular chain offering pizza and comfort foods with a focus on delivery and quick takeout options.
The Keys Piano Bar
10 minutes' walk
Interactive piano bar with live music and sing-alongs, suitable for a fun night out. Family-friendly early evenings available.
Sloppy Joe's Bar
11 minutes' walk
Iconic bar known for live music, dancing, and a lively atmosphere. A staple of Key West nightlife with local beers and drinks.
Key West Theater
2 minutes' drive
Local venue showcasing theatrical performances and live music events. Great for culture enthusiasts and feature great artists.
Green Parrot Bar
15 minutes' walk
Layback vibe with local music several nights a week. Features pool tables and offers a great selection of drinks.
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
Questions of the users
About Southwinds Motel
Can visitors smoke in designated areas outside the rooms on the property?
10 November 2023
Smoking is permitted outside the rooms and throughout the property in designated areas equipped with ash trays for disposal.
What are the check-in hours for the motel? Is it possible to arrive later in the evening?
15 December 2023
The lobby is open 24 hours, so guests can check in any time of the day or night.
Is there a bar or lounge available on the motel grounds?
22 January 2024
The Tipsy Rooster, located on the property, is a bar that has been recognized as the best in town and offers a variety of drinks.
Are there any fees associated with parking? Are there facilities for locking up bicycles?
5 February 2024
Parking is included in the daily resort fee, and secured bike locking facilities are available for guests.
Can guests smoke on patios outside their rooms?
10 March 2024
Yes, smoking is allowed on patios outside the rooms, but not inside the rooms themselves.
What is the total amount for the resort fee, and what does it cover?
18 April 2024
The daily resort fee is $22.50, which includes parking, breakfast, pool towels, and beach access.
What type of breakfast options are provided for guests?
12 May 2024
A complimentary breakfast featuring coffee, tea, fresh muffins, juice, and other baked goods is offered each morning.
Are there options for bike rentals available for guests to explore the area?
30 June 2024
Bike rentals from a third-party vendor are available on the property for guests to use.
What are the nearby beach access options for guests?
15 July 2024
The motel is just a short walk from a public beach, providing complimentary access to chairs and towels.
How far is the motel from popular attractions like Duval Street and local restaurants?
20 August 2024
The motel is conveniently located just 0.1 kilometers from Duval Street, making it easy to access numerous attractions and eateries in the area.

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