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.
50 photos
SOUTHWINDS MOTEL, Key West
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Key details
About the Hotel
1321 Simonton Street, Key West, 33040,
- Close to South Beach
Very good
7.9
8.6
4.2
4.1
Charming Key West Motel Steps from Duval Street
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
Amenities
The hotel features
Rooms
Southwinds Motel provides a variety of room types to accommodate different needs, including
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
Entertainment
Exploration opportunities abound with local attractions, including the
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.”
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 Beds2 persons30 sq. feet2 King Size BedsAir conditioningCoffee machineroom details
- Standard King Room2 persons19 sq. feet1 King-size bedAir conditioningCoffee machineroom details
- Standard Queen Room2 persons19 sq. feet1 King-size bedAir conditioningCoffee machineroom details
Show all rooms
Room rates & availability calendar
See the best prices and book your dates today!
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Check-in/ Check-out
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
Show more
Southwinds Motel Location
1321 Simonton Street, Key West, 33040,
Explore Key West
Key West Activities & Dining
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
11 minutes' walk
Iconic buoy marking the southernmost point in the continental U.S. Popular photo opportunity.
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
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
2 minutes' walk
Casual eatery offering fresh sandwiches and deli favorites, great for a quick bite or picnic.
The Green Pineapple Cafe
7 minutes' walk
Charming spot for healthy, locally sourced dishes and smoothies. Ideal for health-conscious diners.
Flamingo Crossing
8 minutes' walk
Relaxed atmosphere with eclectic menu options, famous for their seafood selections and cocktails.
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
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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 .
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
Show moreShow less
Pros
Great location
Friendly staff
Comfy beds
Cons
Room expectations
Guest reviewsbased on 1386 reviews
Alison from United Kingdom
Couple
Queen Room Two Queen Beds
3 nights in November 2025
|
Reviewed: February 14, 2026
8.5/10
Convenient Stay near Southernmost Point
convenient location nearby grocery store free laundry detergent included
The hotel is located near the southernmost point that landmark. I found a grocery store across the street. It sells great sandwiches (a real find!). Free laundry facilities were available, including detergent. It was convenient to wash clothes .
The bathroom lacked shelf space. It was difficult to organize toiletries. I found this slightly inconvenient but manageable.
Service
9/10
The front desk staff was helpful. They provided clear directions. They explained the island's attractions. This made planning my visits easier. The staff accommodated a special request I had (much appreciated).
Rooms
8/10
My room contained a microwave and a mini-fridge. These amenities were quite useful. There was a small hanging rack available. I used it for clothing storage. The room had tile floors. They were easy to keep clean.
Location
9/10
The location is near Duval Street, providing easy access to shops. The trolley stop is a short walk away. I found it a convenient form of transportation. Several bars and restaurants are nearby.
Dining
8/10
A free continental breakfast was available to all guests. The breakfast included pre-packaged muffins and instant oatmeal. Coffee and juice were also included in the breakfast offering.
0 Helpful
|
Jonathan from United Kingdom
Couple
Queen Room Two Queen Beds
3 nights in November 2025
|
Reviewed: February 01, 2026
7/10
outdoor space liquor store strange placement full coffee
The location was GREAT for accessing nearby attractions. I really enjoyed the outdoor space by the room. It was a cool spot. Having the liquor store and bar with music was convenient too. Breakfast was fine. Yogurt and coffee worked for me.
The wall mounted TV was partially blocked by the bathroom door. The placement was strange. A full-sized coffee machine with full pot filter packs seemed wasteful. I would never use that MUCH coffee.
0 Helpful
luna from spain
Single
queen room two queen beds
3 nights in November 2025
|
Reviewed: January 18, 2026
8.5/10
excellent stay!
friendly staff complimentary beach attached bar clean pools
i found the staff friendly and helpful . i especially appreciated the complimentary beach access that was provided. a bar and liquor store are conveniently attached to the hotel. i also made use of the two clean pools available .
i noticed limited counter space in the bathroom, which posed a minor inconvenience.
Rooms
8/10
The room featured two queen beds and adequate space. a microwave and mini-fridge were included, providing convenient options for snacks and drinks. It was a useful addition. the air conditioning worked effectively, keeping the room cool and comfortable during the hot days.
Dining
9/10
the complimentary breakfast offered pre-packaged muffins and instant oatmeal. coffee and juice were available each morning. i considered it a satisfactory start to the day, especially with the limited options for a quick bite.
0 Helpful
|
Jordan from United States
Family with children
Queen Room Two Queen Beds
3 nights in November 2025
|
Reviewed: January 14, 2026
9/10
fluffy pillows on-site parking
The room had fluffy pillows and comfortable beds. I enjoyed the continental breakfast. It was convenient. The location was fantastic for exploring the historic area. On-site parking was a bonus.
The pool had leaves in the filter.
0 Helpful
Victoria from United Kingdom
Couple
Queen Room Two Queen Beds
4 nights in November 2025
|
Reviewed: December 08, 2025
9.0/10
lovely surprise
excellent recommendation great location in-room coffee live music
Carlos provided excellent recommendations for local attractions and dining. our room, number one, was conveniently located near the pool and breakfast area. i appreciated the in-room coffee maker, microwave, and mini-fridge. They greatly simplified storing and heating leftovers. plus, the tipsy rooster bar with live music was a definite highlight..
the water pressure in the shower was unfortunately quite weak. it made rinsing off difficult sometimes.
Facilities
9/10
The hotel offers complimentary parking, valuable. guests also have access to beach towels and chairs for use at a nearby beach. It makes beach trips easier. a complimentary breakfast is available in the lobby each morning.
Dining
8/10
A bar and liquor store named tipsy rooster is conveniently located on the premises. It provides drinks and entertainment. rooster treats, an ice cream and donut truck, is also on site. cuban coffee and food are available across the street.
Location
10/10
this location provides great access to nearby attractions. the southernmost point is just a short walk away, and the free on and off bus is easily accessible. simonton street offers easy access to duval street.
0 Helpful
|
Show more reviews
FAQs
About Southwinds Motel
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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