Property building in Southwinds Motel

Southwinds Motel

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Hotel Highlights

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 $450, you can dive headfirst into the Key West experience without breaking the bank.

Decorative detail, Bed in Southwinds Motel
Bedroom in Southwinds Motel

Rooms

Room

Show 6 photos

1 Queen Size Bed

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205 sqft

Standard, Queen Size

Private Bathroom

Microwave

Coffee machine

Flat-screen TV

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 3 photos

1 Sofa Bed

1 Queen Size Bed

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495 sqft

Deluxe

Private Bathroom

Microwave

Coffee machine

Flat-screen TV

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 9 photos

1 Queen Size Bed

1 Sofa Bed

Deluxe, Queen Size, Sofa

Microwave

Flat-screen TV

Discover More

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.

Lobby or reception in Southwinds Motel
Property building in Southwinds Motel

Experience the Best

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!

Photo of the whole room, Bed in Southwinds Motel
Decorative detail, Bed in Southwinds Motel

Plan Your Stay

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.

Breakfast in Southwinds Motel
Lounge or bar in Southwinds Motel

Amenities

Outdoor swimming pool

Air conditioning

Tour desk

Bar

24-hour front desk

Non-smoking rooms

Beach chairs/Loungers

Patio

Lounge or bar in Southwinds Motel
Lounge or bar in Southwinds Motel

Pool

Outdoor

All season, Heated

Swimming pool in Southwinds Motel
Swimming pool in Southwinds Motel
Property building in Southwinds Motel
Check-in was easy, with a map of the property provided. Room was big enough for a short stay (we were there for 6 nights and lived out of our suitcases as there wasn't much storage space). Room was clean enough, though fixtures and fittings were dated. Great location in a generally quieter area, though near enough to a range of decent restaurants. The busier part of Key West is a good walk away, though we only resorted to using the free Duval Loop bus on one occasion, after a long day on our feet. Easy parking close to the room. Didn't get chance to use the pool, but saw others using it, and it looked fine. Breakfast is basic but plenty good enough. You just go to the reception area between 07:00 & 09:00 and take what you want back to the room, which worked fine for us.

Paul

The location of our room was great! Our outdoor chairs faced the street. We sat outside a lot! Most of the staff were exceptional. However, all the other staff were exceptional. Our doorknob was wobbly, and the young lady working, she sent maintenance over right away and he was friendly and fast. Karen that was working Tuesday morning was able to let us stay in our same room so we wouldn't have to move. Our room was clean and fresh. We never used the pools, but they looked nice! The coffee at the free breakfast was great! We don't really eat breakfast, but it always looked clean and replenished. TY for a wonderful stay in Key West! Loved the location too!!

Jodi

The Southwinds was exactly what our family was looking for--an old school type of accommodation that was affordable, clean and walkable to the things we wanted to see. We loved going to the South Beach, a five minute walk, as well as the Southernmost buoy. The ice cream truck on the property was so much fun and there was a small grocery store across the street as well as a bar with music at the hotel. Loved the resident iguanas and roosters. The continental breakfast was perfect---great grab and go items that were a great start for our days of adventure. We would love to return to this fun spot that was a backdrop for some wonderful family memories.

Terri622

The location was amazing, the staff were all very friendly and very helpful! The location has 2 pools, is very close to the beach (3min walk) that includes free towels and chairs, it's directly across from an amazing Cuban Café and small store featuring delicious food and coffee starting at 7am, an ice cream truck on the premises, and adjacent to the Tipsy Rooster whose bartenders were awesome, drinks were delightful, and very good live music daily. It's just far enough away to not be in the "thick-of-it" but close enough to walk everywhere (rent a golf cart/scooter/bicycle or Uber/taxi)

Kimwardle

We would absolutely return to the Southwinds! The entire staff's vibe was happy, respectful, and helpful. The location is perfect for getting to the sunrises by foot and a straight scoot to the other side of the island for sunset. I liked the quiet of the area, as we were able to visit the Southernmost buoy every night without lines, or even car traffic. And we went by foot and scooter, depending on our mood.

Jill

Check-in was easy, with a map of the property provided. Room was big enough for a short stay (we were there for 6 nights and lived out of our suitcases as there wasn't much storage space). Room was clean enough, though fixtures and fittings were dated. Great location in a generally quieter area, though near enough to a range of decent restaurants. The busier part of Key West is a good walk away, though we only resorted to using the free Duval Loop bus on one occasion, after a long day on our feet. Easy parking close to the room. Didn't get chance to use the pool, but saw others using it, and it looked fine. Breakfast is basic but plenty good enough. You just go to the reception area between 07:00 & 09:00 and take what you want back to the room, which worked fine for us.

Paul

The location of our room was great! Our outdoor chairs faced the street. We sat outside a lot! Most of the staff were exceptional. However, all the other staff were exceptional. Our doorknob was wobbly, and the young lady working, she sent maintenance over right away and he was friendly and fast. Karen that was working Tuesday morning was able to let us stay in our same room so we wouldn't have to move. Our room was clean and fresh. We never used the pools, but they looked nice! The coffee at the free breakfast was great! We don't really eat breakfast, but it always looked clean and replenished. TY for a wonderful stay in Key West! Loved the location too!!

Jodi

The Southwinds was exactly what our family was looking for--an old school type of accommodation that was affordable, clean and walkable to the things we wanted to see. We loved going to the South Beach, a five minute walk, as well as the Southernmost buoy. The ice cream truck on the property was so much fun and there was a small grocery store across the street as well as a bar with music at the hotel. Loved the resident iguanas and roosters. The continental breakfast was perfect---great grab and go items that were a great start for our days of adventure. We would love to return to this fun spot that was a backdrop for some wonderful family memories.

Terri622

The location was amazing, the staff were all very friendly and very helpful! The location has 2 pools, is very close to the beach (3min walk) that includes free towels and chairs, it's directly across from an amazing Cuban Café and small store featuring delicious food and coffee starting at 7am, an ice cream truck on the premises, and adjacent to the Tipsy Rooster whose bartenders were awesome, drinks were delightful, and very good live music daily. It's just far enough away to not be in the "thick-of-it" but close enough to walk everywhere (rent a golf cart/scooter/bicycle or Uber/taxi)

Kimwardle

We would absolutely return to the Southwinds! The entire staff's vibe was happy, respectful, and helpful. The location is perfect for getting to the sunrises by foot and a straight scoot to the other side of the island for sunset. I liked the quiet of the area, as we were able to visit the Southernmost buoy every night without lines, or even car traffic. And we went by foot and scooter, depending on our mood.

Jill

Check-in was easy, with a map of the property provided. Room was big enough for a short stay (we were there for 6 nights and lived out of our suitcases as there wasn't much storage space). Room was clean enough, though fixtures and fittings were dated. Great location in a generally quieter area, though near enough to a range of decent restaurants. The busier part of Key West is a good walk away, though we only resorted to using the free Duval Loop bus on one occasion, after a long day on our feet. Easy parking close to the room. Didn't get chance to use the pool, but saw others using it, and it looked fine. Breakfast is basic but plenty good enough. You just go to the reception area between 07:00 & 09:00 and take what you want back to the room, which worked fine for us.

Paul

The location of our room was great! Our outdoor chairs faced the street. We sat outside a lot! Most of the staff were exceptional. However, all the other staff were exceptional. Our doorknob was wobbly, and the young lady working, she sent maintenance over right away and he was friendly and fast. Karen that was working Tuesday morning was able to let us stay in our same room so we wouldn't have to move. Our room was clean and fresh. We never used the pools, but they looked nice! The coffee at the free breakfast was great! We don't really eat breakfast, but it always looked clean and replenished. TY for a wonderful stay in Key West! Loved the location too!!

Jodi

The Southwinds was exactly what our family was looking for--an old school type of accommodation that was affordable, clean and walkable to the things we wanted to see. We loved going to the South Beach, a five minute walk, as well as the Southernmost buoy. The ice cream truck on the property was so much fun and there was a small grocery store across the street as well as a bar with music at the hotel. Loved the resident iguanas and roosters. The continental breakfast was perfect---great grab and go items that were a great start for our days of adventure. We would love to return to this fun spot that was a backdrop for some wonderful family memories.

Terri622

The location was amazing, the staff were all very friendly and very helpful! The location has 2 pools, is very close to the beach (3min walk) that includes free towels and chairs, it's directly across from an amazing Cuban Café and small store featuring delicious food and coffee starting at 7am, an ice cream truck on the premises, and adjacent to the Tipsy Rooster whose bartenders were awesome, drinks were delightful, and very good live music daily. It's just far enough away to not be in the "thick-of-it" but close enough to walk everywhere (rent a golf cart/scooter/bicycle or Uber/taxi)

Kimwardle

We would absolutely return to the Southwinds! The entire staff's vibe was happy, respectful, and helpful. The location is perfect for getting to the sunrises by foot and a straight scoot to the other side of the island for sunset. I liked the quiet of the area, as we were able to visit the Southernmost buoy every night without lines, or even car traffic. And we went by foot and scooter, depending on our mood.

Jill

Location

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

Reservations:

+1 (888) 385-8465

or
Southwinds Motel

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