Southwinds Motel

Hotel with 2 outdoor swimming pools, steps from South Beach

Choose dates to view prices

Where to?

Dates

October 2025

21

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
‪Seaside Cafe at the Mansion - ‬3 min walk
‪La Te Da - ‬5 min walk
‪Southernmost Point Bar in the USA - ‬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

$206 nightly

Nov 4 - Nov 5

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

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

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 21, 2025, prices found for a 1-night stay for 2 adults at Southwinds Motel on Oct 26, 2025 start from $144.53, 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 South Beach. You'll also find Southernmost Point and Ernest Hemingway Home and Museum less than a mile away.

Is there parking available 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.

Does Southwinds Motel have a hot tub?

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.