Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

2 outdoor pools, pool umbrellas, sun loungers

Overview
Rooms
Location
Policies

Excellent

Popular amenities

Bar
24/7 front desk
Laundry
Air conditioning

Explore the area

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

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

Very good

250 sq ft
Sleeps 3
1 Queen Bed

Standard Room, 2 Queen Beds

Excellent

400 sq ft
Sleeps 4
2 Queen Beds

Deluxe Room

Exceptional

300 sq ft
Sleeps 4
1 Queen Bed and 1 Double Sofa Bed

Standard Room, 1 King Bed

Very good

300 sq ft
Sleeps 3
1 King Bed

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
Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
Mallory Square - 4 min drive - 1.3 miles

Getting around

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

Restaurants

‪Southernmost Beach Café - ‬3 min walk
‪Southernmost Point Bar in the USA - ‬5 min walk
‪La Te Da - ‬5 min walk
‪Rum Bar at the Speakeasy Inn - ‬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. You'll find limited parking. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. Additional amenities include laundry facilities, a picnic area, and a vending machine.

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

Pool
Breakfast included
Pet friendly
Free WiFi

$143 nightly

Oct 5 - Oct 6

Total with taxes and fees

Property amenities

Parking and transportation

Limited onsite parking
Wheelchair-accessible parking available

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

If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
No elevator
Wheelchair-accessible parking

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

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

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 28.13 per accommodation, per night

The resort fee includes:

Beach access
Beach loungers
Beach towels
Concierge service
In-room coffee
Internet access
Laundry facilities
Partner property beach club access
Phone calls
Pool access
Self parking

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

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 limited parking.

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 Oct 4, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Oct 5, 2025 start from $134.83, 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 South Beach, 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, there is accessible parking available.

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 good for couples?

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, there isn't a spa tub at this hotel.

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.

Are there connecting rooms at Southwinds Motel?

No, this hotel doesn't feature connecting guestrooms.

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 that I can book at Southwinds Motel?

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

Southwinds Motel Reviews

8.8

Excellent

9.0/10

Cleanliness

9.2/10

Staff & service

8.4/10

Amenities

8.4/10

Property conditions & facilities

8.2/10

Eco-friendliness

4/10 Poor

Keith

Traveled with family

Aug 4, 2025

Disliked: Property conditions & facilities

We were asked when checking in if we used Orbitz, I said yes and she changed my room number. Room assignment was not what was shown on the website or in the photos.

Stayed 5 nights in Jul 2025

6/10 Okay

Deborah

Traveled with partner

Aug 1, 2025

Liked: Cleanliness

The staff was fine, not particularly friendly. Parking was not good. The second pool was out of order, so the one pool was crowded.

Stayed 1 night in Jul 2025

8/10 Good

Michel

Jul 31, 2025

Stayed 1 night in Jul 2025

10/10 Excellent

Elizabeth

Traveled with family

Jul 1, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Always stay at Southwinds. Like the location

Stayed 2 nights in Jun 2025

8/10 Good

Crystal

Jul 1, 2025

Liked: Cleanliness, amenities, property conditions & facilities

It is everything you need. Clean rooms, hot showers, two pools, ice and washer and dryer. Small breakfast and on the quiet end of the adventures. Grocery store across the street, ice cream and bar/restaurant on site. Excellent pricing and friendly staff. Thank you for an incredible girls trip. We will see you soon.

Stayed 4 nights in Jun 2025

10/10 Excellent

James

Traveled with family

Jun 30, 2025

Liked: Cleanliness, amenities

Great location. Good value, small rooms because they have updated a motel from a past era. Friendly helpful staff. Laundry room was a plus.

Stayed 2 nights in Jun 2025

6/10 Okay

Janet

Jun 30, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Bathroom too small

Stayed 3 nights in Jun 2025

10/10 Excellent

Stacey

Traveled with family

Jun 28, 2025

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

Stayed 3 nights in Jun 2025

10/10 Excellent

Susan

Traveled with family

Jun 28, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

This property is amazing. Two pools, one heated. Free laundry (with detergent!). Front desk did magic and got me my room for a second night. Coupon for free umbrella and towels at the beach around the corner. Go get a Classic Cuban from Ana’s Cafe right across the street. Right on the Duval Loop Trolley. Great value for money. Highly Recommend!

Stayed 1 night in Jun 2025

10/10 Excellent

Amy

Jun 26, 2025

Stayed 4 nights in Jun 2025

10/10 Excellent

Cyrenah

Traveled with family and small children

Jun 25, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Was very clean, air conditioner worked very well, pool was good, but closed pretty early. Great value considering its one of the cheaper places in Kwy West. Will definitely be staying there for our next trip.

Stayed 4 nights in Jun 2025

10/10 Excellent

Steven

Jun 25, 2025

Liked: Cleanliness, amenities, property conditions & facilities

My room was very clean and the bed was extremely comfortable. The bathroom was a little small for me but im a 6'4" big guy. Great bar right on the property. Close proximity to just about anywhere a tourist would want to go. Very nice pool. Every guest was very friendly. Staff is extremely helpful and friendly. I loved my stay. I recommend to anyone who wants to visit key west.

Stayed 5 nights in Jun 2025

10/10 Excellent

Linda

Traveled with partner

Jun 24, 2025

Liked: Cleanliness, amenities, property conditions & facilities

The location was perfect! Everything is right there, it's safe and the staff was wonderful!

Stayed 1 night in Jun 2025

10/10 Excellent

Andreanna

Traveled with family

Jun 21, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Clean, great location, and stay.One of the most affordable options in Key West.

Stayed 3 nights in Jun 2025

10/10 Excellent

Mary

Traveled with partner

Jun 20, 2025

Liked: Cleanliness, amenities, property conditions & facilities

This is a wonderful little motel with a great location and very accommodating staff. The rooms are just as advertised and the bed is very comfortable. The bathroom is small but cute. We were pleasantly surprised and very happy with our stay. Both pools are amazing, close to so many key locations for site seeing and oh, the ice cream truck!

Stayed 3 nights in Jun 2025

6/10 Okay

Tequesta

Traveled with partner

Jun 20, 2025

Disliked: Amenities

Location is excellent. Property needs updating especially if they are charging the same rates as fees as surrounding hotels. The check in lady was very rude. Looks like she wanted to go home and busy speaking to others instead of completing my check out. The AC unit in the room barely blew cold air and when we said something they brought us a fan.

Stayed 3 nights in Jun 2025

8/10 Good

Denise

Jun 19, 2025

Disliked: Property conditions & facilities

A little rundown and could be cleaner but area was awesome and very convenient.

Stayed 2 nights in Jun 2025

10/10 Excellent

Thalia

Traveled with family

Jun 18, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

The property has so much parking and even let us park our golf carts that we rented. The staff is so nice.

Stayed 1 night in Jun 2025

8/10 Good

Maximo

Traveled with family

Jun 17, 2025

Liked: Cleanliness, property conditions & facilities

Great location close to everything around old town key west

Stayed 4 nights in Jun 2025

8/10 Good

Dawn

Jun 15, 2025

Stayed 1 night in Jun 2025

10/10 Excellent

Daniel

Jun 14, 2025

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

It is not fancy, but the price was right. A block from Duval. Rent a bike and you will rule! Pool was cleanand well maintained. Pretty 420 friendly. At least no one bothered me about smoking on the property.

Stayed 7 nights in Jun 2025