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Southwinds Motel Key West Exterior photoSouthwinds Motel Key West Exterior photoSouthwinds Motel Key West Exterior photo

Southwinds Motel Accommodation in Key West, Florida

•
8.0|Great
Check rooms and rates
From$153 /nightOnly on Our Website-10%
Check-in
27Oct
Check-out
28Oct
Guests
2 Guests
Key details

About the Hotel

1321 Simonton Street, Key West, 33040
-
Close to South Beach
Great
8.0
8.6
/10
4.2
4.1
/5

Old Town Key West motel with two outdoor pools and on-site Tipsy Rooster Bar

Amenties

Southwinds Motel offers two outdoor pools, one heated and open all year. Free on-site laundry facilities with detergent provided for guest use. The motel provides passes to South Beach with chairs and towels included.

Rooms

All 58 rooms come with a microwave, refrigerator, and plush eurotop matresses. Each room has a cable TV, air conditioning, and a private bathroom with hairdryer. Daily continental breakfast with fresh fruit, yogurt, cereals, and pastries is served in the lobby.

Location

The motel is within a 2-minute walk of Duval Street. The Ernest Hemingway Home and Museun is 12 minutes away on foot. Fort Zachary Taylor Historic State Park is ess than 3.2 km from the property.

Dining & Entertainment

The Tipsy Rooster Bar and Liquor Store features live music daily in the afternoon and evening. Rooster Treats food truck on the property sells soft serve ice cream and mini donuts. A daily continental breakfast with fresh fruit, yogurt, cereals, and pastries is included.

Services & Extras

Bicycle rentals are available on-site through Bone Island Rentals, with delivery to the motel. Guests can use the concierge desk for tour bookings and recommendations. Free on-site parking and a 24-hour front desk are provided.

Highlights

Location: 2-minute walk to Duval Street

Pools: Two outdoor pools, one heated year-round

Rooms: 58 rooms with microwave, refrigerator, eurotop matress

Entertainment: Tipsy Rooster Bar with daily live music

Dining: Rooster Treats ice cream and donut food truck

Extras: Free laundry, bike rentals, South Beach passes

Must-do experiences

  • Visit the Ernest Hemingway Home for a glimpse into his life.
  • Savor a slice of key lime pie at Kermit's for a local treat.
  • Explore the unique exhibits at the Key West Shipwreck Museum.
  • Stroll through the vibrant booths at Mallory Square's sunset celebration.
  • Don't miss the tranquil beauty of Fort Zachary Taylor State Park.

Select your room type

Southwinds Motel offers a range of rooms across the Sunshine State — from double rooms to family suites — complete with breakfast, flexible cancellations, and seasonal deals for your Florida stay
  • Queen Room Two Queen Beds
    2 persons
    325 sq. feet
    2 King Size Beds
    Air conditioning
    Coffee machine
  • Standard King Room
    2 persons
    205 sq. feet
    1 King-size bed
    Air conditioning
    Coffee machine
  • Standard Queen Room
    2 persons
    205 sq. feet
    1 King-size bed
    Air conditioning
    Coffee machine
Show all rooms

Price and Room Availability Calendar

Check availability and prices for your dates now!

Amenities

Southwinds Motel offers amenities for your Florida getaway, from theme park days to coastal escapes
Facilities: Very good
7.8/10Review score

General

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

Guest Parking

  • Private parking is possible on site at .

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
Show more

Southwinds Motel Location

1321 Simonton Street, Key West, 33040
Map view
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
Explore Key West
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
11 minutes' walk
Hemingway's former residence offers guided tours showcasing his life and works along with beautiful gardens.
Duval Street
Duval Street
11 minutes' walk
The vibrant heart of Key West, featuring shops, bars, and restaurants for lively day and night experiences.
Southernmost Point
Southernmost Point
11 minutes' walk
This famous landmark marks the southernmost point in the continental U.S. and is ideal for memorable photos.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
A serene habitat for butterflies and exotic birds, offering educational exhibits and a tranquil environment for visitors.
Water Sports Adventures
5 minutes' drive
Enjoy thrilling activities like jet skiing, kayaking, and paddleboarding with local rental services available.
Yoga Sessions on the Beach
15 minutes' drive
Participate in calming beach yoga sessions with local instructors, perfect for relaxation amidst nature.
Southern Most Deli
Southern Most Deli
2 minutes' walk
A casual spot serving delicious sandwiches and local favorites. Perfect for a quick bite with a laid-back vibe.
The Green Pineapple Cafe
The Green Pineapple Cafe
7 minutes' walk
A charming cafe with a focus on fresh, organic dishes. Vegetarian and gluten-free options are available.
Sloppy Joe's Bar
10 minutes' walk
This iconic bar features live music and a vibrant atmosphere, ideal for a fun night out or casual drinks.
Key West Theater
10 minutes' drive
A local venue showcasing diverse performances ranging from concerts to plays, catering to all ages and preferences.
Getting around Florida
  • City Centre
    Key West 18 min  ·  5000 ft
  • Airports
    Key West International (EYW) 8 min  ·  2.9 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
Private parking is possible on site at .
Internet
Wireless internet is available in the entire hotel at .
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.
Cleanliness
8.1/10
Comfort
8.2/10
Facilities
7.8/10
Free Wi-Fi
8.5/10
Location
9.2/10
Staff
8.5/10
Value for money
7.6/10
Pros
Helpful staff
Good location
On-site bar
Outdoor space
Free parking
Cons
Room maintenance issues
Room cleanliness concerns
Guest reviews
based on 1584 reviews
4.5/5
based on 1448 reviews
8.0/10
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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