Book on our site
Up to 10% cheaper
than Booking.com
Check rooms and rates
From153US$ /night
Check-in
18Jan2026Select date
Check-out
19Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

1321 Simonton Street, Key West, Florida, United States, 33040
-
Close to South Beach
Very good
7.9
8.6
/10
3.8
/5

Location

Southwinds Motel is situated just one block from Duval Street and a short stroll to the Atlantic Ocean. Guests can explore popular attractions like the Hemingway Home and Fort Zachary Taylor State Park within walking distance. The hotel also offers bicycle and electric scooter rentals for easier navigation of the island.

Rooms

Accommodations at Southwinds Motel include various room types featuring Eurotop mattresses for a restful sleep. Guests can choose from Standard Queen, Standard King, and family-friendly rooms with sofa beds, all outfitted with microwaves and mini-fridges. Each room includes complimentary Wi-Fi and cable TV for entertainment.

Amenities

The hotel boasts two outdoor pools offering a refreshing way to relax after exploring the area. Enjoy access to the nearby beach complete with complimentary chairs and towels. Additionally, guests can start the day with a Continental breakfast featuring muffins, pastries, and fresh fruit.

Dining

While Southwinds Motel does not have an on-site restaurant, it is strategically located near an array of dining options. Guests can enjoy fresh seafood, key lime pie, and local specialties at nearby acclaimed eateries. The Tipsy Rooster, located just blocks away, specializes in handcrafted cocktails and local spirits.

Activities

Southwinds Motel's central location allows guests to easily explore the vibrant nightlife of Key West along Duval Street. Visitors can participate in water sports such as snorkeling and jet skiing at Fort Zachary Taylor State Park. The hotel concierge is available to assist in arranging various local adventures.

Highlights

Location: one block from Duval Street

Rooms: Eurotop mattresses

Amenities: two outdoor pools

Dining: fresh seafood

Activities: water sports

Must-do experiences

  • Catch sunset at Mallory Square for live music and local art.
  • Savor a slice of Key Lime Pie at Kermit's for a local favorite.
  • Explore the Ernest Hemingway Home and Museum for literary charm.
  • Visit the haunted Key West Cemetery for a unique historical tour.
  • Check out the Farmers Market on Thursdays for fresh local goods.
View all

Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Queen Room Two Queen Beds
2 persons
325 sq. feet 
2 King Size Beds
Coffee machine
Air conditioning
Standard King Room
2 persons
205 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
Standard Queen Room
2 persons
205 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
Queen Deluxe
2 persons
500 sq. feet 
1 King-size bed
Coffee machine
Air conditioning
Click button to see more rooms
Show all rooms
Show all roomsLess

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • Non-smoking rooms
  • Paid Wi-Fi
  • 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

Location

1321 Simonton Street, Key West, Florida, United States, 33040
Map view
1321 Simonton Street, Key West, Florida, United States, 33040
Nearby
South Street Corner of South and Whithead Streets
Statue Of Bishop Albert Kee
1000 ft
Gallery
Alan S Maltz Gallery
1500 ft
Gallery
Key West Pottery
1700 ft
Gallery
Island Arts Co-op
1700 ft
Gallery
Frangipani Gallery
2000 ft
Restaurants
Southern Most Deli
500 ft
1330 Simonton St
Southernmost Smoothie Shop
1500 ft
1219 Duval St
The Green Pineapple Cafe
1800 ft
1130 Duval St
Flamingo Crossing
2100 ft
1105 Duval Street
Papa John's
2100 ft
538 Truman Ave
Sinz Burritos
2600 ft
500 Truman Ave Unit 1
Key West Cuban Coffee
2000 ft
517 Truman Ave Key West
Tropical Juices & Drinks
2400 ft
925 Duval St
Viva Saloon
2700 ft
903 Duval St
Dons' Place
2100 ft
1000 Truman Ave
Explore Key West
Explore Key West
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 beautiful gardens and guided tours showcasing his life and works.
Duval Street
Duval Street
11 minutes' walk
Famous street buzzing with shops, restaurants, and nightlife that offers a lively atmosphere to soak in.
Key West Butterfly and Nature Conservatory
Key West Butterfly and Nature Conservatory
11 minutes' walk
A serene environment filled with hundreds of butterflies and tropical birds; ideal for nature lovers.
Mallory Square
Mallory Square
25 minutes' walk
Historic waterfront area, renowned for sunset celebrations featuring street performers and local vendors.
Snorkeling at Western Dry Rocks
15 minutes' drive
Thrilling underwater exploration with vibrant marine life; local operators offer gear rentals and tours.
Yoga at the Beach
6 minutes' drive
Relaxation-focused yoga sessions are available at nearby beaches, perfect for unwind and rejuvenation in nature.
Southern Most Deli
Southern Most Deli
2 minutes' walk
Charming deli known for fresh sandwiches and smoothies; ideal for a quick bite before heading out.
The Green Pineapple Cafe
The Green Pineapple Cafe
7 minutes' walk
A cozy spot serving breakfast and brunch with delicious farm-to-table dishes; vegetarian options available.
Flamingo Crossing
Flamingo Crossing
8 minutes' walk
Vibrant atmosphere with a diverse menu; don't miss their signature flamingo pasta dish.
Green Parrot Bar
15 minutes' walk
Iconic bar with live music and a lively crowd; great for enjoying local bands and a casual vibe.
The Waterfront Playhouse
25 minutes' walk
A cozy theater featuring local plays and performances; check their schedule for family-friendly shows.
Getting around
City Centre
Key West20 min  ·  1.0 mi
Airports
Key West International Airport (EYW)8 min  ·  3.0 mi
Want to see Exclusive Early Booking Rate?
Get exlusive rates right now!
Check Rates
Property information and rules
Check-in
from 16:00-23:59
Check-out
from 08:00-11:00
Guest Parking
Paid Private parking is possible on site.
Internet
is available in for additional charge.
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
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 5 km from Key West International Airport.
What amenities are available for guests at Southwinds Motel?
Amenities include two outdoor pools, a bar/lounge area, luggage storage, and free Wi-Fi.
Are bikes available for rent at Southwinds Motel?
Bicycles can be rented on-site for guests to explore the area.
What dining options are available near Southwinds Motel?
Nearby restaurants include Ambrosia (0.5 km), Southernmost Beach Cafe (0.5 km), and Camille's Restaurant (0.5 km).
What is included in the breakfast at Southwinds Motel?
Breakfast includes fresh fruits, coffee, and muffins.
Is parking available at Southwinds Motel?
On-site parking is available for 20 USD per day, and reservation is not needed.
What types of room amenities can guests expect at Southwinds Motel?
Rooms feature air conditioning, flat-screen TVs, microwaves, refrigerators, and plush eurotop mattresses.
How close is Southwinds Motel to the nearest beach?
The nearest beach, South Beach, is 0.5 km away.
Are there laundry services available at Southwinds Motel?
A launderette is available at the property for guests.
Is there a pool available at Southwinds Motel?
Guests can enjoy two outdoor pools at the hotel.
What is the distance from Southwinds Motel to the Ernest Hemingway Home and Museum?
The Ernest Hemingway Home and Museum is 1 km away, about a 12-minute walk.

Next best alternative

Consider them for your next trip.
Check-in
18Jan2026Select date
Check-out
19Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near Southwinds Motel
Santa Maria Suites Resort Key West Exterior photo
Mobile-only price

Santa Maria Suites Resort Key West

9.3
Perfect669 reviews
102m from property
USD 190USD 171
per night
The Southern Cross Tropical Village Key West Exterior photo
Mobile-only price

The Southern Cross Tropical Village Key West

10.0
Perfect1 review
111m from property
USD 872USD 784
per night
Blue Marlin Motel Key West Exterior photo
Mobile-only price

Blue Marlin Motel Key West

8.8
Great4603 reviews
123m from property
USD 143USD 128
per night