/
8.1

1,957 reviews

Southwinds Motel

Southwinds Motel

1321 Simonton Street, Key West, 33040, Florida, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Outdoor swimming pool

Air conditioning

Tour desk

Bar

24-hour front desk

Non-smoking rooms

Beach chairs/Loungers

Patio

Southwinds Motel

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

2.3mi

Most popular amenities

Outdoor swimming pool

Air conditioning

Tour desk

Bar

24-hour front desk

Non-smoking rooms

Beach chairs/Loungers

Patio

View

Free toiletries

Rooms

Queen Deluxe in Southwinds Motel

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.

Standard Queen Room in Southwinds Motel

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.

Show 5 photos

Deluxe, Queen, Sofa Bed

1 Queen Size Bed

1 Sofa Bed

Microwave

Flat-screen TV

+

More details

Queen Room with Two Queen Beds in Southwinds Motel

Show 5 photos

Standard, 2 Queen

2 Queen Size Beds

325 sqft

Private Bathroom

View

Microwave

Coffee machine

x4

+

x3

More details

Standard King Room in Southwinds Motel

Show 3 photos

Standard, King

1 King Size Bed

205 sqft

Private Bathroom

Microwave

Coffee machine

Flat-screen TV

+

More details

Room

Show 5 photos

Deluxe, Triple

x3

+

More details

Standard Room

+

More details

Run of House

x10

+

x6

More details

Guest reviews

8.1

1,957 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

Featured reviews:

🇺🇸

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.

🇺🇸

Michael

8.2

June 2022

Breakfast was good, great location, bike rentals were awesome to get around the island for sight seeing.

🇺🇸

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.

🇺🇸

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.

🇺🇸

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.

🇬🇧

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.

🇺🇸

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. :)

🇺🇸

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.

🇺🇸

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.

🇺🇸

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.

Points of Interest Around Southwinds Motel

Attractions

Key West Butterfly and Nature Conservatory

0.2mi

Southernmost Point of the Continental USA

0.2mi

Key West Lighthouse and Keeper's Quarters Museum

0.4mi

Ernest Hemingway Home and Museum

0.4mi

Duval Street

0.6mi

Key West Cemetery

0.6mi

Edward B. Knight Pier

0.6mi

Fort Zachary Taylor

0.8mi

St. Paul's Key West Episcopal Church

0.8mi

Hard Rock Cafe Key West

0.9mi

Harry S. Truman Little White House

1mi

Key West Garden Club

1mi

Key West Shipwreck Treasure Museum

1.1mi

Mallory Square

1.1mi

Smathers Beach

1.6mi

Pools

Location

  • Outdoor

Features

  • Heated

Availability

  • All season

Amenities of Southwinds Motel

Outdoor swimming pool

Air conditioning

Tour desk

Bar

24-hour front desk

Non-smoking rooms

Beach chairs/Loungers

Patio

View

Free toiletries

Stay rules - Southwinds Motel

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property

Frequently Asked Questions - Southwinds Motel

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.