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Southwinds Motel

Property class: 2

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Photo gallery for Southwinds Motel

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

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air conditioning
  • Parking available
  • Bar

Explore the area

View in a map
1321 Simonton Street, Key West, FL, 33040
  • Place, Duval Street
    ‪3 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

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
(117 reviews)
  • 250 sq ft
  • 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
(95 reviews)
  • 400 sq ft
  • 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)
  • 300 sq ft
  • 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
(137 reviews)
  • 300 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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About the neighborhood

Key West

Located in Old Town Key West, Southwinds Motel is adjacent to South Beach and within a 5-minute walk of other popular sights like Duval Street. This 58-room hotel welcomes guests with 2 outdoor pools, free breakfast, and a bar/lounge.

What's nearby

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

About this property

Southwinds Motel

Guests of Southwinds Motel enjoy access to 2 outdoor pools, coffee in a common area, and free newspapers. Self parking is offered for USD 22.50 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. Additional amenities include laundry facilities, a vending machine, and a picnic area.
Guests can expect to find 32-inch LED TVs with cable channels. Bathrooms offer hair dryers and free toiletries, and pillowtop beds with premium bedding and down comforters ensure a restful night. Other standard amenities include refrigerators, microwaves, and coffee makers. Housekeeping is available on request.
2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

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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
  • Individually decorated
  • Individually furnished
  • 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

  • This property doesn't allow pets

Children and extra beds

  • Free cribs/infant beds are available

Property payment types

  • American Express
  • Diners Club
  • Discover
  • Mastercard
  • Visa

Important information

Fees

You'll be asked to pay these charges at the property:

  • 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

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • Self parking fee: USD 22.50 per day

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 4:00 PM—-midnight
  • Check-out: 11 AM
  • Minimum check-in age: 18
The front desk is open 24 hours a day. Driving? This property offers parking (fees apply).

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A credit card for incidental charges and a government-issued photo ID may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • The minimum check-in age for Spring Break is 18 years old.
  • This property accepts credit cards, debit cards, and cash.
  • The credit card used at check-in for incidentals must be in the name of the primary guest who made the reservation.
  • Onsite safety features include a carbon monoxide detector and a smoke detector.

Additional information about polices, regulations, and more:

  • Registered guests are the only ones allowed in guestrooms.
  • No alcohol is served at Southwinds Motel.
  • There are no elevators.
  • No rollaway or extra beds are available.

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

Is a free cancellation option available at Southwinds Motel?

Southwinds Motel offers free cancellation on some room rates. For specific requirements, look at the cancellation policy on Orbitz.

How much does it cost to stay at Southwinds Motel?

As of Nov 5, 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on Dec 1, 2026 start from $207, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

What's there to do around Southwinds Motel?

This hotel is situated in Old Town Key West, just steps from Florida Keys Beaches and Duval Street, and within a short walk of South Beach. You'll also find Southernmost Point and Ernest Hemingway Home and Museum less than a mile away.

Will I be able to park at Southwinds Motel?

Yes, parking is offered for USD 22.50 per day.

Does Southwinds Motel have a casino at the property?

No, Southwinds Motel doesn't have a casino.

Will I find an indoor pool at Southwinds Motel?

No, this hotel doesn't have an indoor pool; however, there are 2 outdoor pools.

Is Southwinds Motel a good place to stay for couples?

There are plenty of amenities for couples at this hotel, including 2 outdoor pools, proposal/romance packages, and a bar/lounge.

Does Southwinds Motel have a hot tub?

No, this hotel doesn't have a spa tub.

Does Southwinds Motel feature a restaurant that includes a breakfast menu?

Yes, Southwinds Motel serves free continental breakfast at Tipsy Rooster each morning.

Will Southwinds Motel allow pets to stay free of charge?

No, pets aren't allowed at Southwinds Motel.

Does Southwinds Motel have connecting rooms available?

No, there aren't connecting guestrooms at this hotel.

How close is the airport from Southwinds Motel?

The closest major airport to Southwinds Motel is Key West Intl. Airport (EYW), which is 3.2 mi away (8 minutes by car).

Can I book a room with a balcony at Southwinds Motel?

No, you won't find guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 763 out of 1395 reviews
Rating 8 - Good. 375 out of 1395 reviews
Rating 6 - Okay. 165 out of 1395 reviews
Rating 4 - Poor. 59 out of 1395 reviews
Rating 2 - Terrible. 33 out of 1395 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Rooms were clean and beds were very comfortable. All staff were friendly and helpful. This was our 4 th stay here and we will stay here again
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location good place to stay!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent staff and a fun place to stay.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

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

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
great location!
Stayed 4 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good place!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

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

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

6/10 Okay

Liked: Staff & service, property conditions & facilities
Small motel, not fancy. The room was clean and nice off street parking but charged $20 day to park on the premises. The breakfast was good.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A beautiful Key West Motel! Will definitely stay there again!
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good place, clean and quiet.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was fantastic!!
Stayed 7 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very good location! Cute older place it was clean and nice. Great grab and go breakfast.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
Great location. Friendly and helpful staff. Good breakfast. Small, dated room.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Place was close to everything
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness
It was nice
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We spent a long weekend at this hotel for my birthday. The room was nice and cold and the location was great. We especially liked the bar next-door and the Cuban restaurant across the street.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

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

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great hotel, clean and excellent location.
Stayed 2 nights in Mar 2026
Verified review

8/10 Good

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

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our second time staying here. Great location. Fit our needs. Convenient store across the street. Local bar next door. Lots of food options around motel. We’d stay again.
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

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

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Was clean Great location The bar was great
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Adorable motel with a continental breakfast, two pools and a short walk to the beach. I would stay here again.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great overall!
Stayed 4 nights in Jul 2026

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