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Exterior & Views 1, Southwinds Motel, Monroe

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Accommodation Rules

About

Hotel

Southwinds Motel

Monroe, Florida

The Fun Awaits

Perfect for nature loversOnly 209 m to South Beach and 1 km to Higgs Beach

Tourist attractions nearbyOnly 1.2 km to Nancy Forrester's Secret Garden and 1.4 km to Florida Keys National Marine Sanctuary

Reviews

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3.9/5

GoodFrom 101 reviews

5.0/514 May 2026

Eber • Couple Trip

Excelente servicio y muy buen lugar de la propiedad

5.0/58 May 2026

Gwendolyn • Couple Trip

Breakfast food no hot food but would get you by until lunch. Clean room but could use a shelf or vanity to set personal articles on. Room is small but has everything except could use a small chair with a back on it. Nice pool. Staff was great!

5.0/58 May 2026

James

Basic ROOM but FANASTIC location

5.0/58 May 2026

Cindy • Family Trip

Petit-déjeuner à emporter atypique et de bonne qualité, très bon emplacement pour visiter Key West à pied, esprit village vacances chaleureux

5.0/57 May 2026

Debi • Family Trip

Adorable motel with a continental breakfast, two pools and a short walk to the beach. I would stay here again.

5.0/56 May 2026

Richard • Trip with Friends

Very nice place to stay. The breakfast was good, pools were nicely kept very clean and always towels available. The best part was the use of the beach, great chairs and towels provided. The area was very quiet and comfortable

5.0/56 May 2026

Janis L Parks • Couple Trip

Cozy vintage motel. Friendly helpful staff. Continental breakfast daily…plus coffee maker (and supplies), microwave and fridge in room. Walk to many attractions. On-site outdoor bar for your nightcap! We loved it!

5.0/54 May 2026

Billi • Family Trip

We loved our stay! Location was perfect. Could walk to bars and restaurants. Great onsite bar with live music. Room was set up perfectly with space for our family. Staff was wonderful as well. Will definitely stat again!

5.0/54 May 2026

John • Trip with Friends

Satisfied with everything

5.0/52 May 2026

SALVATORE • Couple Trip

Everything was awesome

5.0/527 Apr 2026

Ronnie • Couple Trip

Everything was great. Breakfast was good too.However there was no place to sit for breakfast.

5.0/525 Apr 2026

Casey Shawn • Family Trip

We are SO glad we chosed the Southwinds Motel. If you want the REAL Key West experience go there. We wanted something authentic, not the standard marble and glass hotels that are the same everywhere. Great friendly staff, Great pool, great bar with live music, a full liqour store and ice cream / donut shop all on site. Continental breakfast to start your day. A short walk to the Southern Most point and Duval St. Is only one street over. Surrounded by multiple great restaurants within walking distance. We couldn't be happier with the place, honestly.

5.0/524 Apr 2026

Scott • Couple Trip

That is our second time staying there and we absolutely enjoy the place. We enjoy the location. It’s quick to walk to. We enjoy the beach access. Everybody is so familiar there. We will be staying there again soon.

5.0/523 Apr 2026

Jo Ann • Trip with Friends

Breakfast had a great variety to choise from!

5.0/523 Apr 2026

Robert • Couple Trip

We thoroughly enjoyed our stay here. It is an older property but nice. The staff are very nice and accommodating. The Tipsy Rooster bar was a nice little treat at the property. Ana's Cuban Market is right across the street, which is very convenient. Coffee and light breakfast fare available each morning. Not a huge deal but we wished the bathroom had been a little larger and the shower water flow had been a bit better, but it is an old school motel. A great little gem in the Southernmost area which is quieter and more relaxed but conveniently located to the happenings in and around Duval street.

5.0/521 Apr 2026

Jerome

All good, classic MOTOR HOTEL!

5.0/521 Apr 2026

Christie

This motel was perfect for what we needed. It had breakfast, two pools, a bar and an ice cream shop with donuts. The location was great with the Deli across the street and the food truck across the other street. It was super close to this other most hotel where you can utilize their lounge chairs and it was a great place to sit right on the beach for food. And if you wanted to take a picture with the famous buoy, it was right there. You could also rent golf carts right across the street as well. A nice walk to Duvall Street. I would definitely return because of the ease of everything.

5.0/520 Apr 2026

William • Couple Trip

Was as depicted, clean, fun, good price,

5.0/520 Apr 2026

Khrystyn • Trip with Friends

Had always noticed the South winds Motel right by Tipsy Rooster (my favorite little place in Key West) when I come down but had never stayed until this past weekend. It was perfect for our needs! Plenty of space in the room, including a spacious closet, clean, comfy beds, 2 nice pools to wake you up in the morning after a couple drinks the night before, and while there was limited interaction with the staff, they were great! Easy check-in and out. Truly enjoyed this place and will 100% stay again when I come down next!

5.0/520 Apr 2026

Jennifer • Family Trip

Perfect location for our family vacation to Key West! Very friendly staff, clean rooms, basic continental breakfast (all pre-packaged).

Popular Facilities

Parking

24-hour Front Desk

Luggage Storage

Sports & Recreation

Picnic Area

Public Facilities

Parking (Surcharge)

Vending Machine

Hotel Services

Laundry Service/Dry Cleaning

Luggage Storage

Multilingual Staff

Concierge Services

24-hour Front Desk

Other Facilities

Smoking Area

Food & Drinks

Continental Breakfast

Transportation

Tours/Ticket Assistance

Location

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1321 Simonton Street, Key West, Florida, US

Nearby Destinations

All distances are measured in straight lines. The actual travel distance may be different.

Accommodation Rules

Check-in Procedure

Check-in4:00 PM-midnight

Check-out11:00

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Minimum Spring Break check-in age is 18 years old
The name on the credit card used at check-in to pay for incidentals must be the primary name on the guestroom reservation
This property accepts credit cards, debit cards, and cash
Safety features at this property include a carbon monoxide detector and a smoke detector

Front desk staff will greet guests on arrival at the property.

Want to check in early? Fill out the Special Requests form on the booking page.

More Policies

Only registered guests are allowed in the guestrooms.
Alcohol is not served at this property.
Contactless check-out is available.

About Southwinds Motel

Southwinds Motel Location
Located in Key West (Old Town Key West), Southwinds Motel is within a 5-minute walk of Duval Street and South Beach. This hotel is 0.2 mi (0.3 km) from Southernmost Point and 0.6 mi (0.9 km) from Ernest Hemingway Home and Museum.

Southwinds Motel Facility and Service
Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities, which include bicycles to rent. Additional features at this hotel include concierge services, a picnic area, and a vending machine.

Southwinds Motel Rooms
Make yourself at home in one of the 58 individually decorated guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with down comforters and premium bedding. 32-inch LED televisions are provided, with cable programming available. Private bathrooms with showers feature complimentary toiletries and hair dryers.

Restaurant and Cafe
Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily from 7:00 AM to 10:00 AM.

Room Type and Price

Sun, 16 Aug 2026 - Mon, 17 Aug 2026 (1 night)

1 Room, 1 Adult, 0 Children