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From153US$ /night
Check-in
12Dec2025Select date
Check-out
13Dec2025Select 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
Perfect
8.0
8.6
/10
3.8
/5

Amenities

Southwinds Motel offers two outdoor pools for guests to enjoy during their stay. The hotel provides complimentary beach access complete with chairs and towels for guests. Guests can rent bicycles and Lama Mobility electric kick scooters directly from the hotel for exploring the area.

Rooms

Accommodations at Southwinds Motel include Standard King, Standard Queen, and family-friendly options with additional sofa beds. All rooms come with Eurotop mattresses, microwaves, refrigerators, and 32-inch flat-screen TVs. Guests can take advantage of complimentary Wi-Fi during their stay.

Location

Located just one block from Duval Street, the hotel provides easy access to the best Key West attractions. Guests can visit the Southernmost Point buoy and Higgs Beach within walking distance. The area also offers various dining and nightlife options, making it convenient for exploration.

Dining

Guests can start the day with a complimentary continental breakfast that includes pastries, cereals, and fresh fruit. The hotel is steps away from numerous local dining options that serve fresh seafood and pink key lime pie. Nearby restaurants range from casual eateries to fine dining experiences.

Activities

Southwinds Motel provides an array of local activities such as snorkeling, diving, and visiting historic sites like the Ernest Hemingway Home. Guests can also enjoy the scenic walking paths along Fort Zachary Taylor State Park. A concierge service is available to help plan excursions and activities.

Highlights

Location: one block from Duval Street

Amenities: two outdoor pools

Dining: complimentary continental breakfast

Activities: snorkeling, diving

“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
30 m² 
2 King Size Beds
Coffee machine
Air conditioning
Standard King Room
2 persons
19 m² 
1 King-size bed
Coffee machine
Air conditioning
Standard Queen Room
2 persons
19 m² 
1 King-size bed
Coffee machine
Air conditioning
Queen Deluxe
2 persons
46 m² 
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

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
300 m
Gallery
Alan S Maltz Gallery
450 m
Gallery
Key West Pottery
500 m
Gallery
Island Arts Co-op
510 m
Gallery
Frangipani Gallery
580 m
Restaurants
Southern Most Deli
130 m
1330 Simonton St
Southernmost Smoothie Shop
450 m
1219 Duval St
The Green Pineapple Cafe
540 m
1130 Duval St
Flamingo Crossing
640 m
1105 Duval Street
Papa John's
640 m
538 Truman Ave
Sinz Burritos
770 m
500 Truman Ave Unit 1
Key West Cuban Coffee
590 m
517 Truman Ave Key West
Tropical Juices & Drinks
720 m
925 Duval St
Viva Saloon
810 m
903 Duval St
Dons' Place
610 m
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 West20 min  ·  1.6 km
Airports
Key West International Airport (EYW)8 min  ·  4.9 km
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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 time can I check in and out 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 hotel is 5 km from Key West International Airport.
Is there parking available at Southwinds Motel?
On-site private parking is available without reservation.
What dining options are available near Southwinds Motel?
Nearby restaurants include Ambrosia (0.5 km), Southernmost Beach Cafe (0.5 km), and The Dirty Pig (0.5 km).
What amenities are included in the rooms at Southwinds Motel?
Rooms feature air conditioning, a flat-screen TV, a microwave, a refrigerator, and hair dryers.
Are there any pools at Southwinds Motel?
The hotel offers two outdoor pools, including a heated pool.
Does Southwinds Motel provide breakfast for guests?
Guests enjoy a daily continental breakfast that includes fresh fruits, coffee, and muffins.
Can I find beach access from Southwinds Motel?
Beach access is available with facilities including sun loungers.
Are pets allowed at Southwinds Motel?
Pets are not permitted at the hotel.
Is there Wi-Fi available at Southwinds Motel?
Paid Wi-Fi is accessible throughout the property.

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