"Awesome property. Two pools, bar/liquor store and desert food truck all on premises is kind of hard to beat."
Kevin B from United States
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"The Tipsy Rooster next door is a major plus to the motel."
Susan S from United States
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"The beverage selection in the lobby was great."
Jennifer from United States
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"Great location. Bed was amazingly comfortable!"
Garringer from United States
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"The space was roomy ."
Robin from United States
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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
room details
Standard King Room
2 persons
205 sq. feet
1 King-size bed
Air conditioning
Coffee machine
room details
Standard Queen Room
2 persons
205 sq. feet
1 King-size bed
Air conditioning
Coffee machine
room details
Show all rooms
Price and Room Availability Calendar
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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
City landmarks
Museum
The Ernest Hemingway Home and Museum
2800 ft
Landmark
Duval Street
2800 ft
Square
Mallory Square
1.4 mi
Landmark
Southernmost Point
2800 ft
Nature reserve
Key West Butterfly and Nature Conservatory
2800 ft
Museum
Truman Little White House
1.4 mi
Landmark
USCGC Ingham Maritime Museum
1.8 mi
Cemetery
Key West Cemetery
1.1 mi
Monument
Southernmost Point of the Continental US
2800 ft
Garden
West Martello Tower
2100 ft
Landmark
Curry Mansion
1.1 mi
Event hall
San Carlos Institute Casa Cuba
1.1 mi
Church
Saint Mary Star of the Sea
2800 ft
Aquarium
Key West Aquarium
1.4 mi
Landmark
Key West Lighthouse and Keeper's Quarters Museum
2800 ft
Garden
Nancy Forrester's Secret Garden
1.1 mi
Gallery
The Studios of Key West
4300 ft
Landmark
Key West AIDS Memorial
3200 ft
Beach
Dog Beach
2100 ft
Landmark
Historic E. H. Gato Building
2000 ft
Museum
Tennessee Williams Key West Exhibit
2300 ft
Museum
Key West Shipwreck Treasure Museum
1.4 mi
Gallery
Wild Side Gallery
2400 ft
Museum
Key West Firehouse Museum
2900 ft
Museum
Florida Keys Eco-Discovery Center
1.8 mi
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
11 minutes' walk
Hemingway's former residence offers guided tours showcasing his life and works along with beautiful gardens.
Duval Street
11 minutes' walk
The vibrant heart of Key West, featuring shops, bars, and restaurants for lively day and night experiences.
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
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
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
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.