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Southwinds Motel

2.0 star property
Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Photo gallery for Southwinds Motel

Exterior
Exterior
Reception
2 outdoor pools, pool umbrellas, sun loungers
Property grounds

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Bar
  • 24/7 front desk
  • Laundry

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.)
    ‪7 min drive‬

Room options

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
(96 reviews)
  • 250 sq ft
  • 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

8.6 out of 10
Excellent
(70 reviews)
  • 400 sq ft
  • 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)
  • 300 sq ft
  • 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
(106 reviews)
  • 300 sq ft
  • Sleeps 3
  • 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

  • ‪Seaside Cafe at the Mansion - ‬3 min walk
  • ‪Southernmost Beach Café - ‬3 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk
  • ‪La Te Da - ‬5 min walk
  • ‪Banana Cafe - ‬4 min walk

About this property

Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach
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.

Similar properties

Property grounds
The Palms Hotel
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
8.8 out of 10, Excellent, 1,017 reviews
$184 nightly
The price is $206
Dec 18 - Dec 19
Total with taxes and fees
The Palms Hotel

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
  • Bicycle rentals

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

  • This property doesn't allow pets

Children and extra beds

  • Free cribs/infant beds are available

Property payment types

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 Dec 4, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Dec 9, 2025 start from $132.49, excluding 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 Duval Street and Florida Keys Beaches, and within a short walk of Southernmost Point. You'll also find Ernest Hemingway Home and Museum and Mallory Square within a short drive.

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.

What do couples enjoy most about Southwinds Motel?

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

Are there hot tubs at Southwinds Motel?

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?

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).

Are there rooms with balconies at Southwinds Motel?

No, there aren't any guestrooms with balconies at Southwinds Motel.

Southwinds Motel Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 724 out of 1245 reviews
Rating 8 - Good. 325 out of 1245 reviews
Rating 6 - Okay. 127 out of 1245 reviews
Rating 4 - Poor. 51 out of 1245 reviews
Rating 2 - Terrible. 18 out of 1245 reviews

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

10/10 Excellent

Christine

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Aug 2025

10/10 Excellent

Craig

Liked: Cleanliness, staff & service, property conditions & facilities
Perfect spot! One block off of Duvaul St..Walking distance to the Famous "Lowest spot", Close to beaches, Close to golf cart rentals to drive around Key West! Loved it
Stayed 2 nights in Aug 2025

10/10 Excellent

Jason

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great rooms with great views!
Stayed 3 nights in Aug 2025

8/10 Good

Stephen

Stayed 4 nights in Aug 2025

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, property conditions & facilities
Older property but was perfect for what we needed.
Stayed 1 night in Aug 2025

10/10 Excellent

Simon

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 2 nights in Aug 2025

8/10 Good

James

Traveled with group
Liked: Staff & service, amenities
Will stay again, property needs to be updated
Stayed 7 nights in Aug 2025

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, property conditions & facilities
We absolutely loved it! Very nice rooms. The grounds were well kept( we always seen Staff was amazing (
Stayed 5 nights in Aug 2025

10/10 Excellent

David

Stayed 2 nights in Aug 2025

4/10 Poor

Stacey, RETFORD

Traveled with family
Disliked: Cleanliness, staff & service, amenities, property conditions & facilities
The reviews for this motel were great so I had no worries when I booked it. But it’s fair to say this place is incredibly tired and run down. the exterior of the motel is in need of some tlc, and I hoped that it was only the exterior that was tired. Whilst the rooms were huge, they were badly in need of renovating, there were cracked and peeling walls, and very dated and tired furniture. Whilst it appeared superficially clean it needed a good deep clean. Although we booked 3 nights we left after 2 as we really didn’t feel comfortable here. It could be beautiful if renovated, but with the half hearted staff we saw, I can’t see any changes happening any time soon.
Stayed 3 nights in Aug 2025

6/10 Okay

Aprell

Traveled with family
Close to everything. Very old school check in so process takes forever. Staff is friendly. Continental breakfast has a great spread. Free refreshments all day which is good because it was super hot. Iron was broken but quickly switched out. It’s ok for a short stay
Stayed 2 nights in Aug 2025

10/10 Excellent

Emidio

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Parking was the only semi issue, it fills up fast on the pool side, do not expect to keep the same spot, but everything about the motel was great and I would recommend it anyone
Stayed 4 nights in Aug 2025

8/10 Good

Kenneth

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was very nice and proficient. Allowed me to check in early that was much appreciated!
Stayed 2 nights in Aug 2025

10/10 Excellent

Danielle

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Most afforable in Key West

Friendly and attentive staff. Clean and spacious room.
Stayed 4 nights in Aug 2025

4/10 Poor

Amal

Traveled with family
Disliked: Cleanliness, amenities, property conditions & facilities
old property and needed uplift
Stayed 1 night in Aug 2025

8/10 Good

Jeremy, Roscommon

Stayed 4 nights in Apr 2025

10/10 Excellent

Steve, LENEXA

Stayed 3 nights in Aug 2025

10/10 Excellent

Steve, LENEXA

Traveled with group
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, nice rooms, the staff is super friendly & provides a great vacation experience.
Stayed 3 nights in Aug 2025

10/10 Excellent

Adrienne, Fort Gibson

Traveled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
We liked this cute motel! The ice machine wasn’t working and that’s the only thing I can be negative about. It was great!
Stayed 2 nights in Aug 2025

8/10 Good

Terry

Stayed 2 nights in Aug 2025

10/10 Excellent

Johnnie Allen

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Aug 2025

8/10 Good

Craig

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Aug 2025

10/10 Excellent

Cynthia

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was a great place to stay
Stayed 5 nights in Jul 2025

6/10 Okay

Louise

Traveled with family
Liked: Cleanliness, staff & service
Disliked: Amenities
the room we were given was not handicap friendly. the pool outside our door was out of order. the step into the room was hard to manage with my walker. The girl at check-in was not very friendly and seemed bothered. Nowhere in the room for a handicap person to sit. Brought a chair in from the pool.
Stayed 1 night in Jul 2025

4/10 Poor

Alexandre

Liked: Staff & service
Bed bug on myself and my pregnant wife. :(
Stayed 1 night in Jul 2025

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