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Southwinds Motel

2.0 star property
Unwind with sun-kissed loungers by the pool or enjoy lively entertainment nearby. With bike rentals and tour assistance at hand, adventure awaits.

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Bar (on property) - Southwinds Motel (Key West)
Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated - Southwinds Motel (Key West)
Front of property - Southwinds Motel (Key West)
Property grounds - Southwinds Motel (Key West)
Reception - Southwinds Motel (Key West)
Southwinds Motel is a tropical haven near South Beach, where you can kick back in the outdoor entertainment area or take a dip in one of two pools. Enjoy continental breakfast, bike rentals, and beach towels at your fingertips – plus helpful staff that have earned rave reviews from previous guests.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar

Room options

Available filters for rooms
Showing 4 of 4 rooms

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(107 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 2 Queen Beds

8.8 out of 10
Excellent
(80 reviews)
  • 37 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, individually decorated

Deluxe Room

10.0 out of 10
Exceptional
(7 reviews)
  • 28 sq m
  • Sleeps 4
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 King Bed

8.4 out of 10
Very good
(114 reviews)
  • 28 sq m
  • Sleeps 3
  • 1 King Bed

About the neighborhood

Located near the beach, Southwinds Motel is in Old Town Key West, a neighborhood in Key West. Duval Street and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at South Beach and Clarence S. Higgs Memorial Beach Park. Ernest Hemingway Home and Museum and Mallory Square are two other places to visit that come recommended. Discover the area's water adventures with kayaking, scuba diving, and snorkeling nearby, or enjoy the great outdoors with ecotours. Visit our Key West travel guide
Map
1321 Simonton Street, Key West, FL, 33040

What's nearby

  • Duval Street
    Duval Street
    3 min walk - 0.2 miles
  • South Beach
    South Beach
    3 min walk - 0.2 miles
  • Southernmost Point
    Southernmost Point
    5 min walk - 0.3 miles
  • Clarence S. Higgs Memorial Beach Park
    Clarence S. Higgs Memorial Beach Park
    9 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    9 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW)
    8 min drive

Restaurants

  • Seaside Cafe at the Mansion
    3 min walk
  • Southernmost Beach Café
    3 min walk
  • Circle K
    6 min walk
  • Cuban Coffee Queen (Duval)
    5 min walk
  • Rum Bar at the Speakeasy Inn
    5 min walk

About this property

Southwinds Motel

Hotel near Duval Street
Located close to South Beach and Southernmost Point, Southwinds Motel provides free continental breakfast, laundry facilities, and an outdoor entertainment area. Guests can also expect to find a bar.
You'll also enjoy the following perks during your stay:
  • 2 outdoor pools along with sun loungers and pool umbrellas
  • Self parking (surcharge), coffee/tea in the lobby, and tour/ticket assistance
  • Free newspapers, concierge services, and beach towels
  • Luggage storage, a 24-hour front desk, and outdoor furniture
  • Guest reviews give top marks for the beach locale and helpful staff
Room features
All 58 individually furnished rooms include comforts such as premium bedding and air conditioning. Guest reviews highly rate the clean rooms at the property.
Other amenities include:
  • Highchairs and free infant beds
  • Pillowtop mattresses and down comforters
  • Bathrooms with showers and free toiletries
  • 32-inch LED TVs with cable channels
  • Refrigerators, microwaves, and coffee/tea makers

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Property amenities

Parking and transportation

  • Self parking on site (USD 22.50 per day)

Food and drink

  • Free continental breakfast available daily 7:00 AM to 10:00 AM
  • A bar/lounge
  • Coffee and tea in common areas

Restaurants on site

  • Tipsy Rooster

Things to do

  • 2 outdoor pools

Family friendly

  • 2 outdoor pools
  • High chair
  • In-room crib
  • In-room microwave
  • In-room refrigerator
  • Laundry facilities
  • Pool gate

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Laundry facilities
  • Luggage storage
  • Vending machine

Guest services

  • Concierge services
  • Housekeeping (on request)
  • Multilingual staff
  • Proposal/romance packages
  • Tour and ticket assistance

Outdoors

  • Beach loungers
  • Beach towels
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Pool loungers
  • Pool umbrellas

Accessibility

  • No elevator

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free crib
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Private bathroom
  • Shower
  • Towels provided

Entertainment

  • 32-inch LED TV with cable channels

Food and drink

  • Cleaning supplies
  • Coffee/tea maker
  • Microwave
  • Paper towels
  • Refrigerator

More

  • Access via exterior corridors
  • Air conditioning
  • Electrical adapters
  • Free local calls
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Phone
  • Window screens

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: midnight
Late check-in subject to availability
Minimum check-in age: 18

Check-out

Check-out before 11 AM
Contactless check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Free cribs are available on request at the property

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 33.75 per accommodation, per night
The resort fee includes:
  • Additional inclusions
  • Beach access
  • Beach loungers
  • Beach towels
  • Concierge service
  • In-room coffee
  • Internet access
  • Laundry facilities
  • Partner property beach club access
  • Phone calls
  • Pool access

We have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 22.50 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

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

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms
Alcohol is not served at this property

Property is also known as

Southwinds Motel Key West
Southwinds Motel
Southwinds Key West
Southwind Hotel Key West
Southwinds Motel Hotel
Southwinds Motel Key West
Southwinds Motel Hotel Key West

Frequently asked questions

Does Southwinds Motel have a pool?

Yes, this property has 2 outdoor pools.

Is Southwinds Motel pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is available for USD 22.50 per day.

What time is check-in at Southwinds Motel?

Check-in start time: 4:00 PM; Check-in end time: midnight. Late check-in is available during limited hours.

What time is check-out at Southwinds Motel?

Check-out is at 11 AM.

Where is Southwinds Motel located?

Located in Old Town Key West, this hotel is within a 5-minute walk of Duval Street, South Beach, and Southernmost Point. Ernest Hemingway Home and Museum and Clarence S. Higgs Memorial Beach Park are also within 15 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Southwinds Motel Reviews

8.6

Excellent

8.8

Cleanliness

8.4

Amenities

9.0

Staff & service

8.2

Property conditions & facilities
Rating 10 - Excellent. 730 out of 1319 reviews
Rating 8 - Good. 354 out of 1319 reviews
Rating 6 - Okay. 148 out of 1319 reviews
Rating 4 - Poor. 59 out of 1319 reviews
Rating 2 - Terrible. 28 out of 1319 reviews

Reviews

Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect location for our family vacation to Key West! Very friendly staff, clean rooms, basic continental breakfast (all pre-packaged).
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Elizabeth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Wonderful, pleasant and informative staff.
Stayed 3 nights in Apr 2026
Verified

8/10 Good

Catherine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was good and clean. The staff were nice, and very helpful. I would stay here again. Very affordable.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Deborah

Liked: Cleanliness, amenities, property conditions & facilities
Great location and comfortable stay.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was very clean and the staff was great. I really enjoyed the heated pool.
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I had a great time. The staff was friendly, this is a great location for the price. The Tipsy Rooster was fantastic, the drinks and music were perfect. We will be back
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Khrystyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Sandra

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We absolutely loved our stay! Our room was so quaint and very clean. The pools were lovely and it was nice to have one heated. Location is excellent. We parked our car and walked everywhere.
Stayed 2 nights in Mar 2026
Verified

8/10 Good

Mavis

Liked: Cleanliness
Large spacious room. Good location.
Stayed 2 nights in Feb 2026
Verified

8/10 Good

Grady

The rooms were clean, the staff was polite and helpful, and the provided light breakfast options provided were good.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Karen

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Robyn

Liked: Cleanliness, amenities, property conditions & facilities
Great place to stay. Great location was able to walk everywhere. Pools were both clean and great. Room was small but clean. We will be returning.
Stayed 7 nights in Feb 2026
Verified

6/10 Okay

irene

Liked: Cleanliness
Shopping near. Poolside was nice and pool was clean.
Stayed 1 night in Mar 2026
Verified

8/10 Good

Thomas

Liked: Cleanliness, amenities, property conditions & facilities
Older motel, rooms are kinda small but everything was clean, staff was great, even had free use of laundry facilities, decent breakfast selection with nearby options also available.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Laura

Liked: Cleanliness, amenities, property conditions & facilities
Clean rooms, hot showers, friendly staff, great location! The Tipsy Rooster was a bonus 🙂
Stayed 7 nights in Feb 2026
Verified

8/10 Good

Vincent R.

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Adequate........Close to all amenities..........
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Valerie

Liked: Cleanliness, amenities, property conditions & facilities
Friendly and helpful staff.
Stayed 8 nights in Jan 2026
Verified

10/10 Excellent

Noelle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location! Outside of the Duvall Street bustle but within easy walking distance to everything, including the beach, grocery store and restaurants. The onsite outdoor bar, the Tipsy Rooster, features great drinks and live music. The onsite pools are great. One has plenty of room for the family and the other is heated and provides a quieter, more laid-back and secluded place to relax. My go-to place in Key West for affordability and convenience!
Stayed 4 nights in Apr 2026
Verified

10/10 Excellent

Sherri

Liked: Cleanliness, staff & service, amenities
Wonderful room by the pool. Excellent staff, great location to be able to walk just about anywhere on the island.
Stayed 1 night in Jan 2026
Verified

8/10 Good

anna

Liked: Cleanliness, staff & service, amenities
Clean nice motel
Stayed 6 nights in Dec 2025
Verified

10/10 Excellent

Christie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Brandy Lynn

Liked: Cleanliness, amenities, property conditions & facilities
Super cute! Perfect location. We would stay again.
Stayed 3 nights in Jan 2026
Verified

8/10 Good

Inge Ryberg Hove

Liked: Cleanliness, staff & service, amenities
Very nice room, surroundings, and staff very kind and serviceminded
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Holly

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was so nice, great location.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 7 nights in Apr 2026