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From174US$ /night
Check-in
14Mar2026Select date
Check-out
15Mar2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

1321 Simonton Street, Key West, Florida, United States, 33040
-
Close to South Beach
Very good
7.9
8.7
/10
3.8
4.1
/5

Location

The Southwinds Motel is located just one block from Duval Street and steps away from the Atlantic Ocean. Positioned in Old Town Key West, the hotel offers convenient access to local attractions, popular restaurants, and beautiful beaches. Guests can easily reach Higgs Beach and the historic Hemingway Home on foot.

Amenities

The hotel features two outdoor pools, offering guests a refreshing way to relax and unwind after exploring the island. Complimentary Continental breakfast is provided daily, featuring a selection of pastries, cereals, and fresh fruit. Rentals for bicycles and Lama Mobility electric kick scooters are conveniently available on-site, enhancing the experience of exploring Key West.

Rooms

Southwinds Motel provides a variety of room types to accommodate different needs, including Standard Queen, Queen Room with Sofa Bed, Standard Two Queen, and Standard King options. Each room comes equipped with Eurotop mattresses, microwaves, mini-fridges, and flat-screen TVs for guests' convenience. With inviting and comfortable furnishings, the rooms offer a restful retreat after a day of activities.

Dining

For dining options, the motel is within walking distance of numerous restaurants that embrace the local seafood culture. Guests can savor fresh dishes and specialties at nearby establishments like Louie's Backyard and the Southernmost Beach Café. Additionally, the on-site Tipsy Rooster offers handcrafted cocktails and a selection of spirits to complement guests' relaxation.

Entertainment

Exploration opportunities abound with local attractions, including the Key West Butterfly and Nature Conservatory and Truman Little White House. The vibrant nightlife along Duval Street and the ever-popular Mallory Square provide entertainment options just steps from the motel. Guests can participate in water sports, shopping, and cultural experiences, adding to their Key West adventure.

Highlights

Location: One block from Duval Street

Rooms: Standard Two Queen options

Dining: Tipsy Rooster on-site

Amenities: Two outdoor pools

“This motel strikes me as a solid choice for couples seeking a relaxed Key West experience. The vibe is mellow, with two pools for unwinding and a bar on-site offering live music at a reasonable volume. Plus, its location puts you within walking distance of key attractions and a convenient Cuban café.”
Hotel logo
James DavidEditor-in-Chief at Cheaphotels
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Select your room type

The hotel provides a selection of rooms—doubles, family rooms, and suites—with perks like free cancellation, breakfast options, and great value 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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Amenities & services

Real traveler stories and honest reviews—no glossy ads, just authentic feedback to guide your booking
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
Explore Key West
Key West Activities & Dining
Top Attractions
Activities
Dining
Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
11 minutes' walk
Former residence of author Ernest Hemingway, showcasing his life and works. Guided tours available.
Southernmost Point
Southernmost Point
11 minutes' walk
Iconic buoy marking the southernmost point in the continental U.S. Popular photo opportunity.
Mallory Square
Mallory Square
25 minutes' walk
Vibrant gathering spot known for sunset celebrations and local vendors. Great for people-watching.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
Beautiful indoor tropical habitat home to hundreds of butterflies and exotic birds, with educational exhibits.
Water Sports at Smathers Beach
5 minutes' drive
Thrilling water sports including jet skiing and paddleboarding. Rentals available on the beach.
Yoga Sessions at Higgs Beach
8 minutes' walk
Relaxing beachfront yoga classes ideal for all skill levels. Classes typically require prior registration.
Key West Garden Club
8 minutes' walk
Public garden featuring tropical landscapes and local flora. Free admission and self-guided tours.
Local Art Walk
7 minutes' walk
Monthly event showcasing local artists and galleries. Perfect for art lovers and culture enthusiasts.
Southern Most Deli
Southern Most Deli
2 minutes' walk
Casual eatery offering fresh sandwiches and deli favorites, great for a quick bite or picnic.
The Green Pineapple Cafe
The Green Pineapple Cafe
7 minutes' walk
Charming spot for healthy, locally sourced dishes and smoothies. Ideal for health-conscious diners.
Flamingo Crossing
Flamingo Crossing
8 minutes' walk
Relaxed atmosphere with eclectic menu options, famous for their seafood selections and cocktails.
Southernmost Smoothie Shop
Southernmost Smoothie Shop
6 minutes' walk
Delicious smoothies and light bites perfect for cooling off after a day in the sun. Ideal for all ages.
Green Parrot Bar
15 minutes' walk
Live music venue with a diverse atmosphere. Known for nightly performances and a friendly crowd.
Key West Theater
15 minutes' walk
Host to plays, live concerts, and comedy shows. Check the schedule for family-friendly events.
The Bull and Whistle Bar
12 minutes' walk
Popular nightlife spot with multiple bars and a rooftop area. Known for its lively atmosphere.
Old Town Trolley Tours
10 minutes' drive
Fun guided tours showcasing the historic sites of Key West. Perfect for families and history buffs.
Getting around town
City Centre
Key West18 min  ·  5000 ft
Airports
Key West International Airport (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
Paid Private parking is possible on site.
Internet
Wireless 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

What past guests shared about their stay
Review score
Based on 1293 verified reviews
8.2/10
Great
82%
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
Pros
Great location
Friendly staff
Comfy beds
Cons
Room expectations
Guest reviews
based on 1584 reviews
4.5/5
based on 1814 reviews
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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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.
Which attractions are located near Southwinds Motel?
Nearby attractions include Fort Zachary Taylor State Park (3 km) and The Ernest Hemingway Home and Museum (1 km).
What kind of breakfast is offered at Southwinds Motel?
Guests can enjoy fresh fruits, fresh coffee, and muffins for breakfast.
What amenities are included in the rooms at Southwinds Motel?
Rooms include air conditioning, a flat-screen TV, a microwave, a refrigerator, and hair dryers.
What are the swimming pool options at Southwinds Motel?
The motel features two outdoor pools, including a heated pool, open all year.
Are there any restaurants near Southwinds Motel?
Nearby restaurants include Ambrosia (0.5 km), Southernmost Beach Cafe (0.5 km), and Camille's Restaurant (0.5 km).
How far is Southwinds Motel from Key West International Airport?
The motel is located 5 km from Key West International Airport.
What services does Southwinds Motel provide for guests?
Services include a concierge desk, luggage storage, and on-site laundry facilities.
What kind of lounge or bar services are offered at Southwinds Motel?
The motel features a Tipsy Rooster Bar and Liquor Store for guests to relax.
Is Wi-Fi available at Southwinds Motel?
High-speed Wi-Fi access is available throughout the property.

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Check-in
14Mar2026Select date
Check-out
15Mar2026Select date
Rooms and Guests2 Guests, 1 Room