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Southwinds Motel

2.0 star property

Photo gallery for Southwinds Motel

Bar (on property)
Reception
Property grounds
Standard Room, 2 Queen Beds
Front of property

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Air-conditioning
  • Bar
The current price is AU$262
includes taxes & fees
15 June - 16 June

Explore the area

View 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.)
    ‪12 min drive‬

Room options

View all photos for Standard Room, 1 Queen Bed

Premium bedding, down duvets, pillow-top beds, individually decorated

Standard Room, 1 Queen Bed

8.4 out of 10
Very good
(110 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

Standard Room, 2 Queen Beds

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

View all photos for Deluxe Room

Premium bedding, down duvets, pillow-top 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

Standard Room, 1 King Bed

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

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About the area

Key West

Southwinds Motel places you steps from South Beach and within a short 5-minute stroll of Duval Street. Highlights at this hotel include 2 outdoor swimming pools and free continental breakfast. .Tipsy Rooster is the hotel's own bar, serving drinks along with light fare. Other amenities include coffee/tea in a common area and laundry facilities. Each morning free breakfast is served. There's also the convenience of self parking. .Places within a short walk of this Old Town Key West hotel include Southernmost Point and Ernest Hemingway Home and Museum is within 15 minutes.

What's nearby

  • Duval Street - 3 min walk - 0.3 km
  • South Beach - 3 min walk - 0.3 km
  • Southernmost Point - 5 min walk - 0.4 km
  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 8 min drive

Restaurants

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

About this property

Southwinds Motel

Southwinds Motel offers its guests 2 outdoor swimming pools. You can enjoy a drink at the bar/lounge. Free breakfast is available daily.

A vending machine, multilingual staff, and tour/ticket assistance are also featured at Southwinds Motel. For a fee, parking is available.

Smoking is allowed in designated areas at this Key West hotel.

  • 1 floor
  • 58 guestrooms or units
  • 9 buildings
  • Continental breakfast (free)
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Coffee in lobby
  • Self-service laundry
  • Front desk (24 hours)
  • Staff members are multilingual
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Outdoor picnic space
  • Newspapers in lobby (free)
  • Smoking in designated areas
  • Bar or lounge
Southwinds Motel offers 58 air-conditioned accommodations, which are accessible via exterior corridors, and features coffee/tea makers and a hairdryer. Each accommodation is individually furnished and decorated. Pillowtop beds feature down duvets and premium bedding. Guests can make use of the in-room fridges and microwaves. Bathrooms include a shower and complimentary toiletries.

32-inch LED televisions come with cable channels. Business-friendly amenities include telephones along with free local calls (restrictions may apply). Housekeeping is provided on request.

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Wicker Guesthouse
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  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
4.3 out of 5, Excellent, 1,005 reviews
The price is AU$303
includes taxes & fees
16 June - 17 June
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Property amenities

Parking and transport

  • Parking on site (USD 22.50 per day)
  • Limited on-site self parking

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 cot
  • 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 lift

More

  • 1 floor
  • 9 buildings
  • Designated smoking areas

Room amenities

Bedroom

  • Down comforter
  • Free cot
  • 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

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

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Free cots (infant beds)!

Payment types

Important information

Fees

Guests will be asked to pay the following 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

We've listed all charges provided to us by the property.

Optional extras

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

  • Self-parking fee: USD 22.50 per day

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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 guest room reservation. This property accepts Visa, Mastercard, American Express, Discover, Diners Club, debit cards and cash. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation.

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.
  • Alcohol isn't served at Southwinds Motel.

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

What is the cancellation policy at Southwinds Motel?

Southwinds Motel offers free cancellation on select room rates. Check out the cancellation policy for more info.

How much does it cost to stay at Southwinds Motel?

As of 12 June 2026, prices found for a 1-night stay for 2 adults at Southwinds Motel on 15 June 2026 start from AU$262, 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.

Is parking available at Southwinds Motel?

Yep, Southwinds Motel has a self car park for USD 22.50 per day. A self car park is also available, for a fee.

Are there any beaches close to Southwinds Motel?

Yep, Southwinds Motel is a short 2-minute walk from Florida Keys Beaches. Fun beach activities include snorkelling, scuba diving and parasailing. You can also find boat tours.

Does Southwinds Motel have a pool?

Yep, and guests recommend it! Southwinds Motel has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying under the shade of an umbrella.

What makes Southwinds Motel a romantic place to stay?

Romance packages and a lounge bar, as well as pillowtop beds in the guestrooms, all help set the scene for a romantic weekend at Southwinds Motel.

Is Southwinds Motel family-friendly?

You bet! With amenities such as 2 outdoor pools and laundry facilities, as well as highchairs and free infant beds in the guestrooms, it's no surprise that Southwinds Motel is a hit with families.

Does Southwinds Motel serve breakfast?

Yeah, our visitors speak well of the free continental breakfast here! Served daily from 7:00 AM to 10:00 AM, this is the place to fuel up for a big day of adventure.

Is there a free airport shuttle available at Southwinds Motel?

No, Southwinds Motel does not offer an airport shuttle service.

What time are check-in & check-out at Southwinds Motel?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Are pets allowed at Southwinds Motel?

No, pets are not allowed.

Southwinds Motel Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 735 out of 1353 reviews
Rating 8 - Good. 371 out of 1353 reviews
Rating 6 - Okay. 159 out of 1353 reviews
Rating 4 - Poor. 59 out of 1353 reviews
Rating 2 - Terrible. 29 out of 1353 reviews

8.8/10

Cleanliness

9.0/10

Staff & service

8.4/10

Amenities

8.2/10

Property conditions & facilities

Reviews

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

Kimberly

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

8/10 Good

Rick

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

10/10 Excellent

Hailey

Liked: Cleanliness, amenities, property conditions & facilities
Perfect little place, great location!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Leyany

Liked: Cleanliness, amenities
Very convenient location
Stayed 1 night 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

Keri

Liked: Cleanliness, amenities, property conditions & facilities
Very clean, friendly staff. Super cute. Would stay again.
Stayed 1 night in Feb 2026
Verified

8/10 Good

Sally

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic location and friendly staff.
Stayed 4 nights in Oct 2025
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

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

10/10 Excellent

John

Liked: Cleanliness, amenities, property conditions & facilities
Love this place the people Everytgong
Stayed 3 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

6/10 Okay

irene

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

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities
Always a great stay at the Sea Oats.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Denna

Liked: Cleanliness, property conditions & facilities
Cute comfortable rooms great staff and great location!! Will stay again
Stayed 1 night in Dec 2025
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

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

Judy

Liked: Cleanliness, amenities, property conditions & facilities
The room was very nice and had everything we needed. Checking in and out was so quick and easy with very friendly employees. The breakfast was excellent with plenty of good choices. The location was great with easy walk or bike ride to most things.
Stayed 4 nights in Feb 2026
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

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

Sanda

Liked: Cleanliness, amenities, property conditions & facilities
Clean room, friendly staff, location
Stayed 2 nights in Nov 2025
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

10/10 Excellent

MATTHEW

Liked: Cleanliness, staff & service, amenities
Staff was wonderful, pleasantly surprised that we got free towels and chairs at beach.
Stayed 7 nights in Dec 2025