See all properties

Southwinds Motel

Property class: 2

Choose dates to view prices

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 granite countertop, white cabinetry, and a coffee machine. - Southwinds Motel (Key West)
A motel with a porch, white chairs, and a signboard. - 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)
A modern kitchen with a coffee station, a television, and a display case with baked goods. - Southwinds Motel (Key West)
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.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Bar

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

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
(116 reviews)
  • 23 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Standard Room, 2 Queen Beds

A hotel room with two beds, a TV, and a window with blinds.

Standard Room, 2 Queen Beds

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

View all photos for Deluxe Room

A hotel room with a bed, a bedside table with a lamp, a coffee maker, and a window with blinds.

Deluxe Room

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

View all photos for Standard Room, 1 King Bed

A hotel room with a large bed, a TV mounted on the wall, a small table with chairs, and a window with curtains.

Standard Room, 1 King Bed

8.4 out of 10
Very good
(134 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 Point Bar in the USA
    5 min walk
  • Southernmost Beach Café
    3 min walk
  • Banana Cafe
    4 min walk

Similar properties

Lobby
Authors of Key West Guest House
Key West Historic District
  • Pool
  • Breakfast included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, 1,052 reviews
Authors of Key West Guest House
Compare similar properties

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.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

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. 746 out of 1379 reviews
Rating 8 - Good. 377 out of 1379 reviews
Rating 6 - Okay. 165 out of 1379 reviews
Rating 4 - Poor. 59 out of 1379 reviews
Rating 2 - Terrible. 32 out of 1379 reviews

Reviews

Verified review

8/10 Good

Ed

Liked: Cleanliness, staff & service, amenities
Enjoyed the stay, still a great location, experience, and value.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Friendly staff, clean rooms and property with an old school feel. We enjoyed our stay and will return.
Stayed 1 night in Aug 2026
Verified review

8/10 Good

Michele

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was small and old fashioned, but it had an old Florida vibe that we loved. Everything we needed was there. The staff were very helpful.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Danielle

Liked: Cleanliness, staff & service, amenities
Room was clean and the staff was very helpful. Location of motel was very convenient to get to Duval street
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Tracy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love this property. Second time staying here. Quaint, nothing fancy but wonderful staff and great location.
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good food
Stayed 1 night in Aug 2026
Verified review

8/10 Good

John

Good location and price.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Donald

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great helpful staff. Locations was good, not busy but walkable to busy areas .
Stayed 1 night in Jul 2026
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

10/10 Excellent

Joe

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was very helpful and polite, their staff was professional and helpful. Karen the front desk person was awesome. Very helpful and friendly
Stayed 4 nights in Jul 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

10/10 Excellent

Elizaveta

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice spacious room. You get many coupons for nearby bars. You even get 1 free alcoholic drink from their Bar "Tipsy Rooster" :) We also ordered a golf cart through our motel's receptionist - and it was delivered to the motel. Location is a bit far from all the action of Duval St. But about 25 min walk to Sloppy Joe's. Still close enough NOT to drive :) Good motel for the money and amenities!
Stayed 2 nights in Aug 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

8/10 Good

William

Liked: Cleanliness, staff & service, property conditions & facilities
The staff was very nice. The location was good. It was a good price. The breakfast was OK. Our room is on the small side, but the bed was very comfortable. It was weird. We had no cold water. Yes, the property is dated and it was a little bit too quiet for my liking. and also the beach we could not use the beach and no one told us until we got there. There was a stair was all seaweed washed up on the beach and it smelt very bad.
Stayed 4 nights in Aug 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