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From153US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

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

Rooms: Stay Details

The Southwinds Motel features accommodations with Eurotop mattresses, microwaves, mini-fridges, and 32-inch flat-screen cable TVs. Options include Standard Queen Rooms, Queen Rooms with Sofa Beds, Standard Two Queen Rooms, and Standard King Rooms. Some rooms include patios. Decor may vary.

Dining: Local Flavors

A complimentary Continental breakfast with muffins, pastries, cereals, oatmeal, yogurts, fresh fruit, milk, coffee, tea and juices is offered. The hotel is near restaurants, including Louie's Backyard for conch fritters and Bo's Fish Wagon for seafood. Nearby options on Duval Street include La Trattoria, Blue Heaven Restaurant, Nine One Five Bistro and Wine Bar, Grand Café, Bagatelle, and Mangoes. Caroline's offers a bar with a selection of drinks.

Leisure and Entertainment

The Southwinds Motel has two outdoor pools and beach access with chairs and towels. Bike and Lama Mobility electric kick scooter rentals are available. The Key West Butterfly & Nature Conservatory, home to over 50 butterfly species and 20 exotic bird species, is nearby. Fort Zachary Taylor State Park offers beaches, snorkeling, and a pre-Civil War fort.

Location and Transportation

Located one block from Duval Street and steps from the Atlantic Ocean, the Southwinds Motel is 5 km from Key West International Airport. It is near Mallory Square, the Ernest Hemingway Home and Museum, and the Southernmost Point. The hotel is about 3.5 hours from Miami via US-1.

Hotel Services

The Southwinds Motel provides concierge service, complimentary Wi-Fi, parking, on-site laundry, and housekeeping. It offers beach access with complimentary chairs and towels.

“I noted that this motel offers included parking and a continental breakfast, both definite advantages in Key West. While some rooms show their age, the location near the Southernmost Point provides a good base for exploring, especially if you don't mind a walk or ride to the livelier Duval Street.”
Hotel logo
David MillerEditor, UsFlorida
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Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
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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Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

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
Explore Key West
Experience Key West
Top Attractions
Activities
Dining
Entertainment
Southernmost Point
11 minutes' walk
Iconic buoy marking the southernmost point of the continental US, perfect for photos and enjoying ocean views.
The Ernest Hemingway Home and Museum
11 minutes' walk
Former residence of author Ernest Hemingway, showcasing his life and works, guided tours available.
Duval Street
11 minutes' walk
Vibrant street known for bars, shops, and nightlife, offering a taste of the local culture and entertainment.
Key West Butterfly and Nature Conservatory
11 minutes' walk
Tropical paradise with hundreds of butterflies and exotic birds, featuring tranquil pathways and conservation efforts.
Snorkeling Adventure
5 minutes' drive
Thrilling snorkeling trips to nearby reefs; rentals and guided tours available for all levels.
Yoga Classes
8 minutes' walk
Relaxing yoga sessions in oceanfront studios, perfect for rejuvenation and finding inner peace.
Key West Garden Club
8 minutes' walk
Beautiful gardens showcasing tropical flora, free admission, great for family strolls and picnics.
Southern Most Deli
2 minutes' walk
Local favorite offering fresh sandwiches and deli items in a casual setting; great for quick bites.
The Green Pineapple Cafe
7 minutes' walk
Charming café known for healthy eats, smoothies, and vegetarian options; perfect for brunch lovers.
Flamingo Crossing
8 minutes' walk
Eclectic menu with Caribbean fusion dishes in a laid-back atmosphere; reservations recommended on weekends.
Sloppy Joe's Bar
11 minutes' walk
Famous bar featuring live music, dancing, and a lively atmosphere; perfect for enjoying a night out.
Key West Theater
10 minutes' drive
Cultural hub offering plays, concerts, and community events; a fantastic spot for families and couples alike.
Sunset Celebration at Mallory Square
25 minutes' walk
Daily sunset festivity featuring local artisans, music, and vibrant street performances; family-friendly vibe.
Local transportation
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
FAQs
About Southwinds Motel
What are the check-in and check-out times at Southwinds Motel?
Check-in is at 16:00 and check-out is by 11:00.
How far is Southwinds Motel from Key West International Airport?
The motel is located 5 km from Key West International Airport.
What are some nearby restaurants to Southwinds Motel?
Nearby restaurants include Ambrosia (0.5 km), Southernmost Beach Cafe (0.5 km), and Camille's Restaurant (0.5 km).
What amenities are available at Southwinds Motel?
The motel features two outdoor pools, complimentary Wi-Fi, on-site parking, a bar/lounge, and luggage storage.
What kind of room amenities does Southwinds Motel offer?
Rooms include a flat-screen TV, air conditioning, refrigerator, microwave, and plush eurotop mattresses.
Is breakfast included with a stay at Southwinds Motel?
Daily continental breakfast featuring fresh fruits, coffee, and muffins is included.
What leisure activities can guests enjoy at Southwinds Motel?
Guests can enjoy swimming in two outdoor heated pools and using sun loungers or beach chairs.
How far is Fort Zachary Taylor State Park from Southwinds Motel?
Fort Zachary Taylor State Park is less than 3 km away.
Is there a bar or lounge at Southwinds Motel?
The motel features a lounge bar where guests can relax with drinks.
Does Southwinds Motel provide bicycle rental services?
Bicycle rentals are available on-site for guests to explore the area.
What is the distance from Southwinds Motel to Duval Street?
Duval Street is just a 2-minute walk away from the motel.
What attractions are near Southwinds Motel?
Nearby attractions include the Ernest Hemingway Home and Museum (12 minutes' walk) and Mallory Square (approximately 2 km).

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