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+1-833-728-20411,957 reviews
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$2171321 Simonton Street, Key West, 33040, Florida, United States
Reservations:
+1-833-728-20411,957 reviews
1/25
Outdoor swimming pool
Air conditioning
Tour desk
Bar
24-hour front desk
Non-smoking rooms
Beach chairs/Loungers
Patio
Welcome to Southwinds Motel, your cozy haven in the sun-soaked paradise of Key West! Nestled just 0.9mi from the vibrant heart of the city, our 2-star motel offers the perfect blend of relaxation and adventure. Whether you’re here to soak up the sun by our inviting outdoor swimming pool or explore the charming streets filled with galleries and restaurants, your dream getaway starts here! With prices starting from just $217, you can dive headfirst into the Key West experience without breaking the bank.
Our guests rave about their time at Southwinds, and with nearly 2,000 reviews, the feedback speaks for itself! Imagine unwinding after a day of exploring with a cold drink at our bar, then hopping back to your non-smoking room equipped with all the essentials like air conditioning and free toiletries. Planning a day out? Our friendly 24-hour front desk is more than happy to assist you with local tours and attractions. Just a stone's throw from pristine beaches, our motel is the perfect launchpad for your adventures.
Take advantage of our patio space, where you can relax and enjoy the beautiful weather while lounging in comfort with our beach chairs. For a small additional fee, parking is available on-site, so feel free to bring your car and set off on a picturesque drive along the coast. Whether you're lazing by the pool or exploring the delightful quirks of Key West, Southwinds Motel promises a stay full of fun and unforgettable memories!
As the sun dips below the horizon, the Southwinds Motel transforms into your very own slice of Key West wonder. The outdoor heated pool is not just a place to take a dip; it’s a mini-vacation in itself. Picture yourself floating on a pool lounge while sipping a refreshing cocktail, soaking in the warm breeze, or gathering with friends for some laughter-filled poolside chats. It’s the ideal spot to recharge after a day packed with adventures or simply to enjoy some well-deserved relaxation in a tropical atmosphere.
The fun doesn’t stop at the pool! With a choice of diverse room options suitable for families, couples, or groups of friends, you’ll find that unwinding in your cozy abode is just as enjoyable as stepping outside to explore. Opt for a spacious Deluxe room with a Queen bed and sofa, or settle into the Standard 2 Queen room with plenty of room for everyone. Each of our non-smoking accommodations is designed with your comfort in mind, ensuring that you have everything you need after a sun-soaked day. From cozy beds to invigorating air conditioning, you'll wake up refreshed and ready for another day of adventures in Key West!
Let’s not forget the thrill of exploring Key West itself! The friendly staff at our 24-hour front desk are eager to help you discover local gems and plan your days. Whether it’s a family fishing trip, an adventurous snorkeling tour, or a leisurely evening stroll around the eclectic shops, every moment spent here can be an exhilarating new discovery. At Southwinds Motel, you don’t just stay; you create lasting memories filled with sun, laughter, and a dash of tropical magic!
Closest airports
Key West International Airport
2.3miOutdoor swimming pool
Air conditioning
Tour desk
Bar
24-hour front desk
Non-smoking rooms
Beach chairs/Loungers
Patio
View
Free toiletries
Show 3 photos
Deluxe
1 Sofa Bed
1 Queen Size Bed
495 sqft
Private Bathroom
Microwave
Coffee machine
Flat-screen TV
+
More details
Experience the elegance and comfort of our spacious Queen Deluxe room, featuring a private bathroom, flat-screen TV, and a patio. With ample space to accommodate up to 4 adults and 2 children, this room is perfect for families seeking a relaxing getaway.
Show 3 photos
Standard, Queen
1 Queen Size Bed
205 sqft
Private Bathroom
Microwave
Coffee machine
Flat-screen TV
+
More details
Experience comfort and convenience in our Standard Queen Room, perfect for a couple or small family. This double room features a spacious 205 sqft, a cozy Queen size bed, and private amenities such as a microwave, coffee machine, and flat-screen TV, along with a charming patio for relaxation.
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Deluxe, Queen, Sofa Bed
1 Queen Size Bed
1 Sofa Bed
Microwave
Flat-screen TV
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More details
Show 5 photos
Standard, 2 Queen
2 Queen Size Beds
325 sqft
Private Bathroom
View
Microwave
Coffee machine
x4
+
x3
More details
Show 3 photos
Standard, King
1 King Size Bed
205 sqft
Private Bathroom
Microwave
Coffee machine
Flat-screen TV
+
More details
Show 5 photos
Deluxe, Triple
x3
+
More details
Standard Room
+
More details
Run of House
x10
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x6
More details
8.1
1,957 reviewsCategories of assessments
Cleanliness
Comfort
Location
Facilities
Staff
Value for money
Featured reviews:
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Charles
9.1
August 2022
Great older hotel at the ocean end of Simonton Ave. Great coffee shop on the corner and plenty of food options right in a 1 block radius. Oh yea, Tipsy Rooster right out front with live music most days, bar, and liquor store. 2 nice pools on site. Property is very well maintained. Wi-Fi was problem-free for my wife's online business requirements. Convenient parking onsite. Bike racks, bike rentals, and even onsite scooter rentals.
My only issue was that our room did not have any dressers so we lived out of our suitcases for 5 nites.
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Michael
8.2
June 2022
Breakfast was good, great location, bike rentals were awesome to get around the island for sight seeing.
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Kovarik
9.1
May 2022
At the eastern end of Key West, Southwinds is "close enough" and yet "just far enough away" from the crowds on Duval Street. Everything is easily accessible, so it's nice to get away from the noise. Mornings are so pleasant, listening to the roosters crowing! Room 7 is generous in proportion and it was wonderful to have a kitchen area for our snacks and beverages.
The floor looked clean, but was so dirty that the bottoms of our bare feet were black within minutes. There were no convenience shelves in the shower stall for soap or shampoo, etc. There were no grab rails in the shower stall. There were no bathroom shelves or counter space for personal items.
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Sherri
8.2
September 2023
Great location, complementary washing facilities on site, allowed an hour later check out complementary. Although our room was very clean, it was in great need of updating. Even fresh white paint on the bead board  and wood would be a huge improvement.  It looked old and dated and that would certainly freshen it up.  One of the things that aggravated me was my flight was canceled because of the hurricane that came through Key West and on the western side of the Florida peninsula. The motel would not allow me to cancel one day and come in later. I ended up paying for two nights and didn’t even get to stay there. I feel like that was poor business, and I will probably never stay there again as a result. The front desk staff was not very friendly, but they were helpful.
Even though the rooms were very clean, they were so dated that it looked like they had not been kept up well. Time for a mini facelift.
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Anonymous
10
August 2023
What we liked about the Southwind Motel is that is in oldtown and is close to most museums ,atractions ,restaurants and shopping ,also the beach .It was very peacefull during the day and night ,and the tipsy rooster bar had very happy and good vibes with a music performers every night ,my wife and I loved the place we also use one of the pool which was very clean and warm. Also rooms are very clean and they do the house keeping everyday .Hotel Staff was very nice and welcoming .All around the property was very clean and we also loved the rooster treats ice cream truck in the corner.
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Abha
8.2
August 2023
Many of the reviews talk about the space being outdated or "rundown"... that wasn't our experience. Yes, it is serving shabby chic, but our bed was comfortable, the bathroom big, the A/C (yes a tad loud) working perfectly in what was a heat wave where all of Key West felt like 115 degrees, and everything fit into what we were seeking for the excellent price provided. Many key places within walking distance, a bar next door, buses to get you to the square, and more! Would 100% stay again.
There were a few ants, but we didn't mind them as we were just there for a couple of days. Could have been more shade at the pool.
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Cheryl
10
August 2023
Loved the location, the vibe, the room, the amenities. Would definitely stay again in the slightly off-season when the rates are a bit lower. Easy walk to water, tourist sites, good restaurants, etc. The room was not fancy but it was very beachy and comfortable. The swimming pool was nice and warm. A bar and an ice cream shop on the premises, and across the street from a quaint grocery store/deli/Cuban coffee place. Bikes/scooters available. A couple of blocks from hop on-hop off bus stop. And of course, the ubiquitous KW chickens running around.
Liked it all. It was just BLAZING hot during our visit, but the hotel couldn't do anything about that. :)
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Christine
10
July 2023
It's in a fantastic location. You can walk 5 mins to the beach at the end of the street, or the Dog Beach next door, walk to tons of restaurants, shopping, bars etc. Parked my truck for 2 days! Hotel staff was amazing! Room was small but cute, clean and comfortable for 2 ppl. Bar next door, live music until 11, great vibe, met some amazing ppl. Room was quiet, slept great. Highly recommend.
Breakfast limited to muffins, danishes, coffee, OJ or AJ. Hard boiled eggs in a plastic package, oatmeal. It was OK for our short stay but longer than 2 days, you'd need to find a breakfast spot.
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Marydean
9.1
August 2023
I loved nearly everything ❤️ two pools to choose from, 1 is heated. There each surrounding the rooms. The room was HUGE with a bar! Our fridge was big enough and it fit our bag of ice! Their services came every day around 11. Semi attached was a bar with live music 🎶 🎵 ❤️ we were located around the corner from everything. I wish I didn't have to leave!
Unfortunately, they did not have any options for streaming......no Netflix, hulu, etc. You have to really work to find the sweet spot for the water pleasure. I found it. My friend, however, did not.
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Jenna
10
May 2023
The staff was fantastic. Friendly, SUPER helpful with getting me a golf cart delivered to the property and when exiting they returned it for me. I love the drink machine in the lobby and the delicious coffee provided in the morning. The cleaning staff was friendly and very prompt each day. Our room was very clean and comfortable. When you enter the property driveway, you are instantly in a private secluded area that makes you really feel like you are on vacation. You are close to a food truck, across the street from a small grocery store for last-minute and other items you may need. I cannot say enough about this place. We will DEFINITELY be back soon. This is the perfect Key West spot.
I have ZERO complaints or dislikes about the property.
Attractions
Key West Butterfly and Nature Conservatory
0.2miSouthernmost Point of the Continental USA
0.2miKey West Lighthouse and Keeper's Quarters Museum
0.4miErnest Hemingway Home and Museum
0.4miDuval Street
0.6miKey West Cemetery
0.6miEdward B. Knight Pier
0.6miFort Zachary Taylor
0.8miSt. Paul's Key West Episcopal Church
0.8miHard Rock Cafe Key West
0.9miHarry S. Truman Little White House
1miKey West Garden Club
1miKey West Shipwreck Treasure Museum
1.1miMallory Square
1.1miSmathers Beach
1.6miAttractions
Key West Butterfly and Nature Conservatory
0.2miSouthernmost Point of the Continental USA
0.2miKey West Lighthouse and Keeper's Quarters Museum
0.4miErnest Hemingway Home and Museum
0.4miDuval Street
0.6miKey West Cemetery
0.6miEdward B. Knight Pier
0.6miFort Zachary Taylor
0.8miSt. Paul's Key West Episcopal Church
0.8miHard Rock Cafe Key West
0.9miHarry S. Truman Little White House
1miKey West Garden Club
1miKey West Shipwreck Treasure Museum
1.1miMallory Square
1.1miSmathers Beach
1.6miAirports
Key West International Airport
2.3miLocation
Features
Availability
Outdoor swimming pool
Air conditioning
Tour desk
Bar
24-hour front desk
Non-smoking rooms
Beach chairs/Loungers
Patio
View
Free toiletries
Bathroom
Bathtub or shower
Free toiletries
Hairdryer
Private Bathroom
Toilet
Toilet paper
Cleaning Services
Laundry
Food & Drink
Bar
Vending machine (drinks)
Food & drink safety
Delivered food covered securely
Food can be delivered to guest accommodation
Front Desk Services
24-hour front desk
Baggage storage
Concierge
Tour desk
General
Air conditioning
Heating
Non-smoking rooms
Internet
Wifi
Kitchen
Coffee machine
Microwave
Refrigerator
Living Area
Sitting area
Media & Technology
Cable channels
Flat-screen TV
Radio
Telephone
TV
Outdoors
Outdoor furniture
Patio
Parking
Parking On Site
Private Parking
Physical distancing
Cashless payment available
Contactless check-in/out
Room Amenities
Fan
Iron
Sofa bed
Safety features
Access to healthcare professionals
First aid kits available
Spa
Beach chairs/Loungers
Outdoor swimming pool
View
View
From 16:00
Guests are required to show a photo identification and credit card upon check-in
From 08:00
Until 11:00
Pets are not allowed.
WiFi is available in all areas and charges apply.
Age restriction may apply
Private parking is available on site (reservation is not needed) and charges may apply.
Reservations
Call us for our best daily rates
+1-833-728-2041Child policies
Children of all ages are welcome.
Children 18 and above are considered adults at this property.
To see correct prices and occupancy info, add the number and ages of children in your group to your search.
Crib and extra bed policies
No capacity for extra beds or cribs.
Cash
American Express,
Visa,
Mastercard,
Discover,
Diners Club
This property does not accept cash.
When are the check-in and check-out times for Southwinds Motel?
For Southwinds Motel, you can check in after 04:00 PM and the check-out deadline is 11:00 AM.
Is free parking available at Southwinds Motel?
Yes, the Southwinds Motel provides parking for its guests. The parking is private and located on-site. While charges may apply, there is no need for a parking reservation.
How much does a stay at Southwinds Motel cost?
A stay at Southwinds Motel can begin from a rate of $217. This is subject to change based on room selection and travel dates. For a clear price, input your desired stay dates.
What types of rooms does Southwinds Motel offer?
The Southwinds Motel offers a variety of room options for guests. This includes the Queen Deluxe room with a sofa bed and queen size bed, the Queen Room with Two Queen Beds, the Standard Queen Room with a queen size bed, and the Standard King Room with a king size bed. None of the rooms allow smoking and have different occupancy capacities ranging from 2 adults and 1 child to 4 adults and 2 children.
Which amenities can guests enjoy at Southwinds Motel?
Guests at Southwinds Motel can spend their time enjoying the leisure amenities provided by the hotel. One of the main attractions is the outdoor swimming pool, which is available to guests all year round. The pool is equipped with a heating system, allowing guests to enjoy a swim even during cooler seasons.
Additionally, the hotel provides beach chairs and loungers, allowing guests to relax and soak up the sun while enjoying the beautiful beachside views. The presence of a bar within the hotel allows guests to enjoy their favorite drinks and socialize with other guests.
Overall, guests at Southwinds Motel can spend their time indulging in the hotel's leisure amenities such as swimming in the outdoor pool, lounging on the beach chairs, and enjoying drinks at the bar.
Does Southwinds Motel feature a pool area?
The Southwinds Motel has one pool available. It is an outdoor pool that is heated and is available for all seasons.
What methods of payment does Southwinds Motel accept?
Southwinds Motel accepts American Express, Mastercard, Discover, Diners Club, and Visa credit cards as methods of payment. Cash is not accepted.
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