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

Southwinds Motel is a tropical haven near South Beach, where you can kick back in the outdoor entertainment area or take a dip in one of two pools. Enjoy continental breakfast, bike rentals, and beach towels at your fingertips – plus helpful staff that have earned rave reviews from previous guests.

Excellent

Popular amenities

Bar
Laundry
24/7 front desk
Air conditioning

Room options

Check availability for these dates

Tonight

Oct 4 - Oct 5

Tomorrow

Oct 5 - Oct 6

All rooms

1 bed

2 beds

Showing 4 of 4 rooms

Premium bedding, down comforters, pillowtop beds, individually decorated

Standard Room, 1 Queen Bed

Very good

Highlights

Individually furnished

Individually decorated

Air conditioning

Free cribs/infant beds

Refrigerator

LED TV

Ceiling fan

Down duvet

250 sq ft
Sleeps 3
1 Queen Bed

Standard Room, 2 Queen Beds

Excellent

Highlights

Individually furnished

Individually decorated

Air conditioning

Free cribs/infant beds

Refrigerator

LED TV

Ceiling fan

Down duvet

400 sq ft
Sleeps 4
2 Queen Beds

Deluxe Room

Exceptional

Highlights

Individually furnished

Individually decorated

Air conditioning

Free cribs/infant beds

Refrigerator

LED TV

Premium bedding

Sofa bed

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

Standard Room, 1 King Bed

Very good

Highlights

Individually furnished

Individually decorated

Air conditioning

Free cribs/infant beds

Refrigerator

LED TV

Renovated in 2016

Premium bedding

300 sq ft
Sleeps 3
1 King Bed

About the neighborhood

1321 Simonton Street, Key West, FL, 33040

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 near Duval Street

Located close to South Beach and Southernmost Point, Southwinds Motel provides free continental breakfast, laundry facilities, and an outdoor entertainment area. Adventurous travelers may like the cycling at this hotel. Guests can also expect to find a bar.

You'll also enjoy the following perks during your stay:

2 outdoor pools along with sun loungers and pool umbrellas
Bike rentals, coffee/tea in the lobby, and a 24-hour front desk
Concierge services, tour/ticket assistance, and luggage storage
A vending machine, free newspapers, and outdoor furniture
Guest reviews give top marks for the beach locale and helpful staff

Room features

All 58 individually furnished rooms include comforts such as premium bedding and air conditioning. Guest reviews highly rate the clean rooms at the property.

Other amenities include:

Highchairs and free infant beds
Pillowtop mattresses and down comforters
Bathrooms with showers and free toiletries
32-inch LED TVs with cable channels
Refrigerators, microwaves, and coffee/tea makers

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

Pets not allowed

Children and extra beds

Children are welcome

Rollaway/extra beds are not available

Free cribs are available on request at the property

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

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

We have included all 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

We should mention

This property does not have elevators

Only registered guests are allowed in the guestrooms

Alcohol is not served at this property

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

Does Southwinds Motel have a pool?

Yes, this property has 2 outdoor pools.

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 7, 2025 start from $127.49, 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.

Is Southwinds Motel pet-friendly?

No, pets are not allowed at this property.

How much is parking at Southwinds Motel?

Limited spots are available.

What time is check-in at Southwinds Motel?

Check-in start time: 4:00 PM; Check-in end time: midnight. Late check-in is available during limited hours.

What time is check-out at Southwinds Motel?

Check-out is at 11 AM.

Where is Southwinds Motel located?

Located in Old Town Key West, this hotel is within a 5-minute walk of Duval Street, South Beach, and Southernmost Point. Ernest Hemingway Home and Museum and Clarence S. Higgs Memorial Beach Park are also within 15 minutes.