Southwinds Motel Key West Exterior photoSouthwinds Motel Key West Room photoSouthwinds Motel Key West Exterior photo

SOUTHWINDS MOTEL, Key West

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Check rooms and rates
From$153 /night
Check-in
20Aug
Check-out
21Aug
Rooms and Guests2 Guests, 1 Room

About the Hotel

1321 Simonton Street, Key West, 33040-
Close to the beach

Key Highlights

Two outdoor pools, including one heated pool, with towels and sun loungers provided.

On-site bar and liquor store (Tipsy Rooster) with live music and a food truck offering pizza and ice cream.

Free beach passes for South Beach (5-minute walk) including chairs and towels.

Complimentary continental breakfast with coffee, tea, juice, and fresh muffins.

Free guest laundry with washer, dryer, and detergent provided.

Private on-site parking included in the daily amenity fee.

Hotel Details

Location

Located in Old Town Key West, a 2-minute walk from Duval Street and a 5-minute walk to South Beach.
The motel sits one block from the quieter southern end of Duval Street and one block from South Beach, offering easy access to dining, bars, and attractions without being in the loudest party area. The Ernest Hemingway Home and Museum is a 12-minute walk away, and Mallory Square is a 15-20 minute stroll. For longer trips, the free Duval Loop bus stops nearby, and bike rentals are available on site. Key West International Airport is a 10-minute drive; no shuttle service is provided, but taxis are readily available. Private parking is included in the amenity fee and is available on site with no reservation needed, though spaces can be limited during peak times.

Accommodation

Ground-floor rooms with private bathrooms, air conditioning, and essential kitchenettes; some include porches.
All rooms are on the ground floor and feature a microwave, small refrigerator, coffee maker, and a flat-screen cable TV. Bed options include queen, king, and rooms with two queen beds or a queen bed with a pullout sofa. Some rooms have private porches, while king rooms do not. Bathrooms are private but often described as compact, with limited counter space for toiletries. Room sizes vary - standard doubles are approximately 220 sq ft. Storage is minimal: most rooms have a hanging rack rather than a closet or dresser. Rooms at the front of the property may experience noise from the on-site bar's live music, while back-facing rooms tend to be quieter. The property is older and the decor in some rooms reflects this, but cleanliness is generally maintained.

Dining

Complimentary grab-and-go continental breakfast in the lobby; on-site bar with pizza and live music.
The morning breakfast is included in the amenity fee and consists of individually wrapped muffins from a local bakery, coffee, tea, orange juice, and sometimes hard-boiled eggs or yogurt. This is a self-service setup with items collected from the lobby. For other meals, the on-site Tipsy Rooster bar serves pizza and drinks, and a food truck called Rooster Treats offers ice cream and doughnuts. Across the street, Ana's Cuban Cafe provides full breakfast and lunch options. Numerous restaurants are within a 2- to 5-minute walk, including Ambrosia, The Lobster Shack, Camille's Restaurant, and Louie's Backyard. The motel does not have a full restaurant or room service.

Wellness and Leisure

Two outdoor swimming pools, including one heated pool, with complimentary towels and sun loungers.
The motel offers two outdoor pools: a larger main pool and a smaller, quieter heated pool located near the back of the property. Both are open year-round and are surrounded by sun loungers and beach towels. Guests also receive passes to South Beach, a 5-minute walk away, which include the use of chairs and towels. The property has outdoor seating areas with tables, chairs, and umbrellas. Bike rentals are available from a third-party vendor on site for exploring the island. For dry Tortugas excursions, the Yankee Freedom Ferry or seaplane services are accessible from the island.

Facilities and Services

24-hour front desk, concierge service, luggage storage, free laundry, and private parking.
The motel provides a 24-hour front desk with concierge assistance for restaurant recommendations, tour bookings (e.g., snorkeling trips), and transport arrangements. Luggage storage is available free of charge. Guest laundry facilities with one washer and one dryer are provided at no extra cost, including detergent. Private on-site parking is included in the daily amenity fee and does not require a reservation. Wi-Fi is available throughout the property and is covered by the amenity fee. The front desk can also help arrange bike or scooter rentals. The property does not have an elevator as all rooms are ground-level, and ramps can be added for accessibility upon request.
Highly rated by guestsof Southwinds Motel
Clean roomsFree breakfastQuiet locationConvenient place
  • Guest Parking

    Parking Paradise

    “Free parking right outside our room made everything so easy. No more circling the block!”

    Kevin from Canada
    Review on
  • Dining

    Morning Treats

    “The free breakfast offered a good start to the day, with coffee, muffins, and yogurt.”

    Mei from China
    Review on
  • Room Features

    Homey Comforts

    “Our large room had a fridge, microwave, and coffee maker. Very convenient!”

    Rajesh from India
    Review on
  • Spa & Leisure

    Poolside Bliss

    “Two clean pools offered the perfect way to cool off after a day of sightseeing.”

    Isabelle from France
    Review on

Critical Operational Notes

  • Check-in from 16:00, check-out by 11:00; early check-in is not guaranteed.
  • A daily amenity fee of $22.50 covers parking, Wi-Fi, breakfast, beach passes, and pool towels.
  • Housekeeping is provided only every three days; request additional service at the front desk.
  • Pets are not allowed; only certified service animals with proper paperwork are accepted.
  • Smoking is permitted only in designated outdoor areas.
  • Wi-Fi is available at an additional charge unless covered by the amenity fee.
  • A refundable security deposit of $150 may be required at check-in.
  • No cots or rollaway beds are available on site.

Most popular facilities

at Southwinds Motel
Paid Wi-Fi
Parking
Luggage storage
24-hour services
Food/ Drinks
Swimming pool

Top Strategic Tips

  • 01

    Book a room at the back of the property to avoid noise from the bar's live music which continues until midnight.

  • 02

    Use the free Duval Loop bus or rent a bike on site to explore the island; the motel is a 20-minute walk from the Key West Express terminal.

  • 03

    Plan for limited in-room storage; rooms lack closets and dressers, making them better suited for short stays.

  • 04

    Request a room with a porch if outdoor seating is preferred; not all room types include one.

Choose your room type

Southwinds Motel — double rooms, family rooms, and suites. Breakfast options and free cancellation available on selected rates
  • Queen Room Two Queen Beds
    2 persons
    30 sq. feet
    2 King Size Beds
    Air conditioning
    Coffee machine
  • Standard King Room
    2 persons
    19 sq. feet
    1 King-size bed
    Air conditioning
    Coffee machine
  • Standard Queen Room
    2 persons
    19 sq. feet
    1 King-size bed
    Air conditioning
    Coffee machine
Show all rooms

Hotel Price Calendar

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August 2026 - August 2027
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Check-in/ Check-out

Facilities

What's included at Southwinds Motel — facilities and services available during your stay
Facilities: Very good
7.8/10Review score

General

  • Non-smoking rooms
  • Paid Wi-Fi
  • On-site car park
  • Handicap parking
  • 24-hour reception
  • No pets allowed
  • Luggage storage
  • Vending machines

Services

  • Laundry
  • Tours/Ticket assistance

Dining

  • Bar/ Lounge area

Spa & Leisure

  • Heated swimming pool
  • Outdoor swimming pool
  • Sun loungers

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Patio
  • Garden furniture
  • Ironing facilities

Bathroom

  • Free toiletries

Media

  • Flat-screen TV
Show more

Southwinds Motel Location

1321 Simonton Street, Key West, 33040
Explore Key West
Local Highlights
  • Top Attractions
  • Activities
  • Dining
  • Entertainment
The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum
11 minutes' walk
Hemingway's former residence, featuring guided tours and lush gardens, an essential cultural visit.
Southernmost Point
Southernmost Point
11 minutes' walk
Iconic buoy marking the southernmost point in the continental US, perfect for photo ops.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
A serene habitat with hundreds of butterflies, offering educational tours and a beautiful experience.
Mallory Square
Mallory Square
25 minutes' walk
Famous for its sunset celebrations, shops, and street performances, offering a lively atmosphere.
Snorkeling Tours
10 minutes' drive
Exciting snorkeling trips available at nearby coral reefs, with gear rentals and guided options.
Yoga on the Beach
8 minutes' drive
Relaxing sessions on the beach, suitable for all levels. Check local listings for class times and prices.
Kayaking
10 minutes' drive
Guided kayaking tours through mangroves and estuaries, perfect for nature enthusiasts.
Southern Most Deli
2 minutes' walk
Casual eatery offering fresh sandwiches and local specialties. Great for a quick and tasty meal.
The Green Pineapple Cafe
7 minutes' walk
Charming cafe known for its healthy options, organic ingredients, and vibrant atmosphere.
Flamingo Crossing
8 minutes' walk
Vibrant spot with Caribbean flavors and a lively setting, perfect for casual dining with friends.
Green Parrot Bar
12 minutes' walk
Popular bar known for live music and a laid-back vibe. Ideal for enjoying local tunes and drinks.
Tropic Cinema
20 minutes' walk
Charming independent cinema showcasing recent films and classics in a cozy setting, great for a relaxed night out.
Getting around
  • City Centre
    Key West 18 min  ·  5000 ft
  • Airports
    Key West International (EYW) 8 min  ·  2.9 mi
Book early and pay less
See available rates for your dates
Check Rates
Property information and rules
Check-in
from 16:00-23:59
Check-out
from 08:00-11:00
Guest Parking
Private parking is possible on site at .
Internet
Wireless internet is available in the entire hotel at .
Breakfast
At the hotel Southwinds Motel guests are invited to a full breakfast served for free.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are not allowed.
Languages
English, Spanish, Russian, Latvian
Number of rooms:
58
Former name
Southwind Motel

Guest Reviews and Ratings

What guests said after staying at Southwinds Motel
Review score
Based on 1441 verified reviews
8.1 /10
Great
80 %
Recommend
Breakfast
6.2/10
Cleanliness
8.1/10
Comfort
8.1/10
Facilities
7.8/10
Free WiFi
8.5/10
Location
9.2/10
Paid Wi-Fi
8.4/10
Staff
8.6/10
Value for money
7.5/10
Pros
Clean room
Great location
Comfortable bed
Cons
Hollow door
Small bathroom
Noisy music
Guest reviews
based on 1584 reviews
4.5/5
based on 1562 reviews
7.9/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews
FAQs
About Southwinds Motel
What are the check-in and check-out times at Southwinds Motel?
Check-in is from 16:00 and check-out is by 11:00.
How far is Southwinds Motel from Key West International Airport?
The hotel is located 5 km from Key West International Airport.
What dining options are available at Southwinds Motel?
Guests can enjoy a daily continental breakfast along with drinks at the Tipsy Rooster Bar and Liquor Store.
What are some nearby attractions to Southwinds Motel?
Nearby attractions include the Ernest Hemingway Home and Museum (1 km) and Fort Zachary Taylor Historic State Park (3 km).
What amenities can guests expect in the rooms at Southwinds Motel?
Rooms include air conditioning, a flat-screen TV with cable channels, a microwave, and a refrigerator.
Does Southwinds Motel have any pools for guests?
The hotel features two outdoor pools, including a heated pool.
What languages are spoken by the staff at Southwinds Motel?
The staff is multilingual and primarily speaks English.
Is there bicycle rental available at Southwinds Motel?
Bicycle rentals are available on-site for guests to explore the area.
What kind of breakfast does Southwinds Motel serve?
Breakfast includes fresh fruits, coffee, and muffins.
How far is Southwinds Motel from the beach?
The hotel is located 0.5 km from South Beach.
What type of view can guests enjoy from Southwinds Motel?
Many rooms offer views of the lush tropical landscapes surrounding the property.

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