Located in the Old Town section of Key West, our top rated motel puts you right in the middle of some of the most popular restaurants and nightlife in town.
A vacation to the Florida Keys wouldn’t be the same without fresh local seafood and waterfront dining. With nearly perfect weather year-round, you’ll find plenty of outdoor options with an emphasis on island flavors. You’ll also find a wide variety of international dishes, vegetarian cuisine and island specialties including conch fritters and Key Lime pie. In typical Old Town Key West style, dining options can range from food trucks to candlelit dining rooms with spectacular ocean views.
Camille’s: Just one block from Southwinds Motel, Camille’s Restaurant has been a local favorite for over 20 years. Their quirky pink building on Simonton serves breakfast, lunch and dinner and offers a Wild Alaskan Snow Crab special on Tuesday, Wednesday & Saturday.
Southernmost Beach Café: At the southern end of Duval Street, Southernmost Beach Café is located directly on South Beach. Enjoy a casual dining atmosphere and specialty cocktails at this open air restaurant offering one of the best views in town.
Caroline’s: Located right on Duval Street, enjoy people watching at this open air restaurant while dining on some of the best Conch fritters in town. Caroline’s offers a cool, relaxed atmosphere, fresh local ingredients and a bar where the staff serves up all your favorite libations.
Blue Heaven: A free spirited outdoor restaurant, Blue Heaven is famous for their colorful tables and chairs, great food, and local chickens and roosters that may stop by to say hello to diners. Located in Bahama village, its eclectic menu includes items such as Caribbean shrimp deglazed with Red Stripe beer and jerk chicken.
A&B Lobster House: For a special night out, plan a meal at this elegant 2nd floor restaurant located on the Bight Marina. With white tablecloths and spectacular harbor views, A&B Lobster House can be counted on for the freshest local seafood and an unforgettable culinary experience.
Conch Republic Seafood Company: Also located on the Bight Marina, Conch Republic Seafood Company (known as “Conch Farm” to the locals) is a favorite for fresh seafood, happy hour specials and fun, Key West ambiance.
Half Shell Raw Bar: The cover art for Kenny Chesney’s “When I See This Bar” single, Half Shell Raw Bar is a favorite for fresh seafood and casual atmosphere at the Historic Seaport. It’s also the only seafood restaurant in Key West that runs its own Fish Market.
Turtle Kraals: Turtle races, oyster bar and fresh seafood ceviche are just a few of the specialties at this Historic Seaport bar. Head up to the upper deck and enjoy unbeatable views of the marina and a front row seat to the sunset.
Duffy’s Steak & Lobster House: Open since 1948, Duffy’s arguably serves the finest steaks and seafood in Key West in a casual atmosphere at affordable prices. From prime rib to whole fresh Maine or Florida lobster, Duffy’s decadent menu won’t disappoint.
The Commodore Waterfront: Another Historic Seaport option, the Commodore is located on the second floor above The Boat House restaurant. The premiere waterfront view is complemented by excellent service and delicious menu items like yellowtail snapper “Cayo Hueso” and bone-in rib eye steak.
Abbondanza: The winner of “The People’s Choice” for favorite Italian restaurant in Key West for many years, Abbondanza offers an extensive selection of pasta and other Italian favorites. Its Old Town Key West location, friendly atmosphere and great service make this a top choice for locals and visitors alike.
Mangia Mangia: Known for their fresh homemade pasta, Mangia Mangia’s delicious menu offers spaghetti with green-lipped New Zealand mussels and a variety of other pasta dishes. Mangia Mangia is located in the heart of Old Town at the corner of Southard and Margaret streets and offers both indoor and outdoor patio seating.
Antonia’s: Located on Duval Street, Antonia’s is a Key West landmark serving handmade pasta created in-house daily. They specialize in finely crafted sauces, pristine local seafood and a carefully curated bar to ensure a delicious meal you won’t soon forget.
Bien: At the corner of Eaton and Grinnell, this Caribbean Latino restaurant is a top choice on TripAdvisor for good reason. Try the slow roasted pork shoulder, steak, and/or chicken breast sandwiches with a side of fire roasted corn and black beans & rice.
El Siboney: A bit of a hidden treasure, El Siboney is located in the small mid-town neighborhood on Catherine Street. The Cuban cuisine menu features a variety of authentic Cuban meals including pork, beef, seafood and chicken dishes.
El Mason de Pepe: Located in Mallory Square, El Mason de Pepe has been crafting authentic Cuban food and drinks for over 30 years. Dine in or visit their patio bar after the sunset celebration for a fresh mojito and live music performance.
Ambrosia Sushi: Right across the street from Southwinds Motel you’ll find Key West’s most popular Sushi Bar, Ambrosia. Open since 1998, Ambrosia meticulously crafts the finest sushi and Japanese food on the island. Elegant décor and its prime location make Ambrosia the perfect choice for a celebration.
Origami Sushi Bar: For a Key West casual option, Origami Sushi Bar is located in Duval Square and offers a quaint garden patio looking out onto the square. This Japanese Bistro complete with fresh sushi bar is the perfect casual dining option.
Bad Boy Burrito: Featured on the Food Network’s “Diners, Drive-Ins and Dives”, Bad Boy Burrito is only 2 blocks from the motel and is our top choice for delicious burritos or homemade soft corn tacos packed with fresh local seafood.
Amigo’s: A tortilla bar with casual bar counter seating, Amigo’s is the perfect place to people-watch while sipping a cold Corona and enjoying a Baja fish burrito. They’re also the “Home of the Square Taco”, a taco machine they invented to hold more fillings with less spilling!
Garbo’s Grill: At the Northern end of Duval, you’ll find another “Diners, Drive-Ins and Dives” sensation: Garbo’s Grill. The eclectic menu also features fresh local seafood, but it’s known for its Umami burger featuring ½ pound of Angus beef, Applewood bacon and chipotle Gouda.
Banana Café: Back at our end of Duval, Banana Café is known for their rooftop terrace and authentic French flavors. Their breakfast, lunch and dinner menu offer a wide variety of options including delicious homemade crepes & quiches.
Key West is also well known for its world famous nightlife scene. Though the island is only 4x2 miles in size, there are over 360 liquor licenses, providing you with plenty of options to de-stress. From low-key bars to clubs, Key West’s nightlife never has a shortage of fun, cocktails or live music.
Sloppy Joe’s: As the slogan states, it’s a “Key West Tradition” to stop at Hemingway’s favorite local bar who even gave it its name while he was living in Key West. Now the bar is one of the main attractions in town serving up food, cocktails and live music every day of the week.
Captain Tony’s Saloon: The oldest bar in Florida, Captain Tony’s Saloon was also the original location of Sloppy Joe’s from 1933-1937. This bar gets its extra flair from bras hanging from the ceiling and business cards covering the walls.
Green Parrot: Though you can find live music pretty much anywhere in Key West, the Green Parrot bar has been named one of the best live music venues in Florida. Bands from around the world perform onstage during Friday, Saturday and Sunday 5:30 to 7pm “soundchecks” followed by a second late night performance.
Irish Kevin’s: “I came, I drank…I don’t remember” is not only the slogan, but also likely a warning! Entertainers encourage audience participation in their performances at this fun Irish themed bar.
Hog’s Breath: This world famous bar is a popular Key West watering hole complete with shop, restaurant and bar. Conveniently located at the corner of Front and Duval streets, they stand behind the fact that “Hog’s Breath is Better Than No Breath at All!”
Schooner Wharf: A Key West classic, the Schooner Wharf is located in the Key West harbor providing patio seating and live band performances. They serve breakfast, lunch, dinner and late night snacks in this low-key bar on the water.
The Porch and The Other Side: The old Porter Mansion on the corner of Duval and Caroline street houses 2 different bars on the 1st floor with porch seating. The Porch has a laid back vibe and features craft beer and wine, while The Other Side offers a lounge-like atmosphere and signature cocktails.
Vino’s: This quaint wine bar has an extensive wine collection that is constantly changing to keep selections fresh and exciting. Enjoy a glass on the porch overlooking Duval Street or in its cozy, vintage setting.
Rick’s: Key West’s largest entertainment complex features 8 bar venues, each offering a different experience from the rest. Options include a dance club, live music & sports bar, tree bar on Duval and more.
Fat Tuesday’s: A world famous chain, Fat Tuesday’s frozen daiquiris are guaranteed to cool you off after a long day on the town. This lively venue has a DJ every night and is one the hot dancing venues on Duval.
La Te Da: This downtown cabaret is only 3 blocks away from the Southwinds Motel. La Te Da features an outdoor bar and restaurant as well as nightly performances from Christopher Peterson, Randy Roberts and more.
Aqua: At this popular Key West bar & nightclub, “Reality is a Drag” and drag is a reality! Nightly shows include performances from the Aquanettes with singing, dancing and comedy.