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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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Photo gallery for Southwinds Motel

An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store". - Southwinds Motel (Key West)
A modern kitchen with a coffee station, a television, and a display case with baked goods. - Southwinds Motel (Key West)
A motel with a porch, white chairs, and a signboard. - Southwinds Motel (Key West)
A modern kitchen with a granite countertop, white cabinetry, and a coffee machine. - Southwinds Motel (Key West)
A white decorative sculpture in a garden area with a white fence and a building in the background. - 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

A hotel room with a bed, a wardrobe, a door, a microwave, and a bathroom with a toilet and towel rack.

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(112 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

Standard Room, 2 Queen Beds | Premium bedding, down comforters, pillowtop beds, iron/ironing board

Standard Room, 2 Queen Beds

8.6 out of 10
Excellent
(84 reviews)
  • 37 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Deluxe Room

Premium bedding, down comforters, pillowtop beds, iron/ironing board

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, iron/ironing board

Standard Room, 1 King Bed

8.4 out of 10
Very good
(124 reviews)
  • 28 sq m
  • 1 bedroom
  • Sleeps 2
  • 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

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    3 min walk - 0.2 miles
  • A beach with people sunbathing, palm trees, and a multi-story building in the background.
    South Beach
    3 min walk - 0.2 miles
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    5 min walk - 0.3 miles
  • A beach with a bridge, palm trees, and a clear blue sky.
    Clarence S. Higgs Memorial Beach Park
    9 min walk - 0.5 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    9 min walk - 0.5 miles

Getting around

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

Restaurants

  • Circle K
    6 min walk
  • Cuban Coffee Queen (Duval)
    5 min walk
  • Southernmost Beach Café
    3 min walk
  • Rum Bar at the Speakeasy Inn
    5 min walk
  • Southernmost Point Bar in the USA
    5 min walk

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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

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. 740 out of 1361 reviews
Rating 8 - Good. 372 out of 1361 reviews
Rating 6 - Okay. 160 out of 1361 reviews
Rating 4 - Poor. 58 out of 1361 reviews
Rating 2 - Terrible. 31 out of 1361 reviews

Reviews

Verified review

10/10 Excellent

Roxanne

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay! The staff was awesome!
Stayed 3 nights in Jun 2026
Verified review

8/10 Good

janice

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay because you are close to everything. Walls are thin so it can get loud. Good breakfast, great pool and super helpful staff.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Erin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a good stay. Close to the ocean and restaurants.
Stayed 3 nights in May 2026
Verified review

8/10 Good

Raul

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very courteous and helpful. Our room was very clean and comfortable. A good, fresh variety of items, along with coffee. milk, and juices were available for breakfast.
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Caridad

Liked: Cleanliness, staff & service, amenities
Clean and cozy pool area.
Stayed 2 nights in Jun 2026
Verified review

8/10 Good

Kamryn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good location
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Sourav

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location and staff were great. Toilets were clean but, it would be better if there are exhaust fan in toilet.
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Steven

Liked: Cleanliness, staff & service, amenities
Great place - can walk to most activities- place a bit dated - decent breakfast- staff super friendly- would stay again.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Deborah

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

10/10 Excellent

Dakota

Liked: Cleanliness, amenities, property conditions & facilities
Pool was nice. Breakfast was minimalist but good. Location is great
Stayed 4 nights in May 2026
Verified review

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 review

8/10 Good

Richard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small, clean & tidy room. Good location for walking around. Little bar next door had great live music.
Stayed 2 nights in May 2026
Verified review

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 review

10/10 Excellent

Kimberly

Wonderful location, had everything we needed!
Stayed 3 nights in Jan 2026
Verified review

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 review

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 review

10/10 Excellent

Dmytro

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Older but remodeled inside hotel. Very clean and fresh. A bit noisy AC. Decent breakfast. Sweet spot. Extremely close to everything. Will book again
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Basic bare bones room, not new, its a motel but what else do you need in Key West, place to sleep and shower, this is a place to crash and isnt fancy but location is great, market across the street, bar and liquor store in front of motel, 5 min walk to Duvall and 1 block from beach. It does the job and has a pool too and parking!!!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Kathleen

Liked: Cleanliness, staff & service, amenities
It's an old motel so it is aged. But, it is well maintained, the staff was wonderful,, the location was ideal, and the price was very reasonable for Key West.
Stayed 6 nights in May 2026
Verified review

8/10 Good

Rick

Liked: Cleanliness, staff & service, property conditions & facilities
Room was nice staff was nice
Stayed 1 night in Feb 2026
Verified review

6/10 Okay

Sabrina

Disliked: Staff & service, amenities
Great location. I rented a car & didn't drive it my entire visit. I was able to walk everywhere. Liquor store & bar built in, so that's convenient. Lol It's definitely an older Motel, so things are older. I was surprised when she handed me an actual key for my room. You don't see that any more 😁
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Memphis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The rooms are nice. They provide necessary amenities and are cleaned well. Not a lot of space, but fair for a motel setting. There is loud music next door at a bar, which I enjoyed, but that’s something to be aware of if you’re a light sleeper. The staff was helpful and this area of the island was very nice. Overall, it was a nice stay!
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Karen

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

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 review

8/10 Good

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The rooms were very clean and had everything we needed. Coffee pot/microwave/refrigerator was a plus - every hotel we look for has to have those three things. The staff was friendly and was able to check us in early. The only issue was the noise factor - our rooms were close to the front of the property so the music from the bar and traffic from the street was a bit frustrating because we are used to quiet, but other than that the stay was great.
Stayed 3 nights in May 2026