Southwinds Motel
Motel, 2-star1321 Simonton Street, Key West, FL, United StatesShow on map
Fabulous
Guests rate it highest for location, amenities and service.
8.62,681Reviews- Check-in from 4:00 PMCheck-out by 11:00 AM. The front desk is staffed around the clock, so a late arrival is fine.
- Exceptional locationGuests rate the location 10.0 out of 10, at 1321 Simonton Street.
- Parking on siteAvailable at a charge the property sets.
Luxurious Amenities Experience comfort and convenience with our plush eurotop mattresses, daily continental breakfast, and beach access for a perfect getaway.
Leisure and Entertainment Relax by one of our two outdoor pools or grab a drink at the Tipsy Rooster Bar and Liquor Store. Enjoy Duval Street just a short stroll away for shopping and dining.
Concierge Services and Location Take advantage of our concierge desk for local tips and bicycle rentals to explore nearby attractions like the Ernest Hemingway Home and Museum. Book your stay at Southwinds Motel now for a memorable Key West experience.
What this place offers
- WiFi available
- Parking
- Non-smoking rooms
- Air conditioning
- Swimming pool
- 24-hour front desk
- Heating
- Laundry
- Luggage storage
- Bar
Rooms
8.6
Fabulous
Rated 8.6 out of 10 by 2,681 guests who stayed here.
- Cleanliness8.3
- Service8.8
- Location10.0
- Rooms7.7
- Amenities9.3
- Value7.7
- Food & drink8.3
Guests mention
Great locationFriendly staff
TeresaUnited StatesAwesome place and we will be back!
Friendly staff, wonderful location and beautiful pool
Rooms are accommodating and comfy just not updated but tyhe price to stay there reflects that
SemmlerGermanySehr freundliches,emphatisches Personal.Besonders möchte ich Karen hervorheben,sie gab uns sehr gute Tipps zum shoppen,einkaufen,Strände und Aktivitäten. Wir waren 3x in Key West,davon 2x im Southwinds Motel.Wir werden…
LORENZOItalyDelusione soprattutto per la maleducazione del personale al checkin
Pulizia della camera
Personale al checkin svogliato, sgarbato e maleducato, struttura vecchia e fatiscente, camera da 2 + 2 con letto da fare.
MariángelesArgentinaLa habitación muy linda
EvaSpainLa ubicación, la limpieza, las camas cómodas, el horario de la piscina
marcoItalyBellissimo soggiorno
La posizione al centro . Le piscine . Parcheggio gratuito .
Colazione da migliorare.
Divano letto da rinnovare .
Reviews are written by guests who booked through our supplier and stayed, shown as written and in their own language. Category scores are the supplier’s reading of recent reviews, updated January 2026.
Where you’ll be
1321 Simonton Street, Key West, FL, United States
Guests rate the location 10.0 out of 10 — exceptional.
Things to know
Cancellation
Each room shows its own terms before you pay.
Most rates can be cancelled free until a date shown on the room.
Non-refundable rates are marked as such.
House rules
Check-in from 4:00 PM
Check-out by 11:00 AM
Children welcome
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No pets
Paid parking on site
Non-smoking rooms available
Payment & property
Paid when you book, not at the desk.
Rates include the taxes and fees we can read.
The property may take a card at check-in for incidentals.
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Guests under the age of 18 can only check in with a parent or official guardian. Please note that the resort fee includes: - Continental Breakfast - Wireless Internet - Beach Access - Lounge Chairs - Towels. Please note parking on site is available for a daily fee of $20.00 plus taxGuests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. A deposit may be required at the property.
What we’d check for you here
- That the step-free room is actually free on your dates, and whether it is a roll-in shower or a bath, which the listing never says.
- That the desk is staffed when you land, and that the room is held past cut-off.
- Whether there is room for a pickup, a trailer or a van, not just a car.
- Whether the rate moves for your dates, and what it includes.
- What the property actually charges at the desk on top of the rate.
Questions about Southwinds Motel
What time is check-in and check-out at Southwinds Motel?
Check-in is from 4:00 PM. Check-out is by 11:00 AM. If you're arriving late, tell us and we'll ask the property to hold the room.
Does Southwinds Motel allow pets?
No — the property states that pets are not allowed.
Is there parking at Southwinds Motel?
Yes — parking is available on site at a charge the property sets. We check the rate and whether a space can be reserved against your dates.
Does Southwinds Motel have a pool?
Yes — a pool is listed among the property's facilities. Seasonal closures are common, so we'll confirm it's open for your dates.
Does Southwinds Motel have Wi-Fi?
Yes — internet access is listed among the property's facilities.
Does Southwinds Motel have wheelchair accessible rooms?
The property lists step-free or accessible facilities. That flag is the one least able to settle the question: a hotel can carry it and still have a step at the entrance, or a bath rather than a roll-in shower, and it does not say whether the accessible room is free on your dates. Tell us what you need and we'll ask the property directly rather than reading you the flag.
Can I check in late at Southwinds Motel?
The property lists a front desk staffed 24 hours, so a late arrival should be possible. Standard check-in is from 4:00 PM. Rooms are still released after a cut-off at some properties regardless of the desk hours, so tell us your arrival time and we'll have them hold it.
How do I book Southwinds Motel?
Put your dates in above and book online, or call (888) 789-8585 and we'll do it for you — including things a booking form can't handle, like a block of rooms, a monthly rate or an invoice for your employer.
Where is Southwinds Motel?
1321 Simonton Street, Key West, FL.
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