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Best Historic Restaurants in South Eola

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16 restaurants available nearby

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A photo of KRES CHOPHOUSE restaurant
1. KRES CHOPHOUSE
4.9
Exceptional(5652)
££££
• Steak • Downtown Orlando
Booked 53 times today
The present and past pair beautifully at Kres Chophouse, a classic, top tier Steakhouse with a modern eclectic flair. This premier Steakhouse embodies the heart of Orlando's historic district, featuring chic and elegant décor within the striking architecture of a 1930's landmark. A thoughtful layout with luxurious banquettes and private dining options create an intimate dining atmosphere.Kres Chophouse specializes in house aged, hand cut prime steaks and the freshest seafood, sourcing quality ingredients that emphasize authenticity over pretension. The full bar boasts a diversified and well-curated wine list as original as the art on the walls, with a weeknight happy hour featuring half priced appetizers at the bar.Easy valet parking and the bustling nightlife of Orlando's legendary Church Street create an extraordinary dining experience for a night on the town!
A photo of Russell's on Lake Ivanhoe restaurant
2. Russell's on Lake Ivanhoe
4.5
Awesome(1426)
££££
• Contemporary American • Downtown Orlando
Booked 9 times today
Located on the historic Lake Ivanhoe, Russell's offers an upscale casual dining restaurant and bar featuring an innovative and fresh menu, all with an amazing view and atmosphere.Chef Emmanual Clement has created a varied and exciting menu based on his international experience.Some of our favorite suggestions include:Artisan Charcuterie Board, Roasted Beets & Burrata Napoleon & Octopus Escabeche (we cure our own meats)Entrees: Grilled Swordfish with Sorrel Sauce, Crispy Duck Confit & Tenderloin Au Poivre (all sauces made fresh in house)Desserts: White Chocolate Bread Pudding with Whiskey Sauce & Cranberry Crème Brulée (all our desserts are made in house)Awards:Top Tables 2020Best Burger 2021 Orlando Sentinel Foodie AwardBest Ambiance; Editor's Choice Orlando, The City's MagazineBest Brunch: Readers' Choice Orlando, The City's MagazineIf you any dietary requirements just let us know ahead of time and we will try and accommodate you.See you soon!
A photo of The Chapman restaurant
3. The Chapman
4.8
Exceptional(728)
££££
• Contemporary American • Winter Park
Booked 23 times today
Nestled in the heart of Winter Park, The Chapman enjoys a prime location on the charming and vibrant Park Avenue, surrounded by the city’s rich history, upscale boutiques, and picturesque lakes. The Chapman brings a fresh perspective to fine drinking and dining, where discovery meets comfort and indulgence. Warm, stylish, and artful with a distinctive Winter Park Florida look and feel, we invite you to celebrate the best of Florida while our hospitable team strives to pamper you and make every gathering truly memorable.
A photo of Charley’s Steak House-Orlando, FL restaurant
4. Charley’s Steak House-Orlando, FL
4.7
Exceptional(6765)
££££
• Steakhouse • I Drive / Sand Lake
Booked 57 times today
Charley’s Steak House on Orlando’s iconic International Drive has been a Florida favorite since 1992, proudly owned by the Woodsby family. Specializing in USDA Prime and Choice Angus beef from three-year-old steers, each steak is aged 4–6 weeks, hand-cut daily by the management team, and flame-grilled over a 1,200º Florida citrus and oak wood fire for unmatched flavor. The ambiance is upscale yet inviting, with rich wood accents and a lively energy. Guests can also enjoy outdoor dining on the spacious patio, perfect for soaking in the Florida breeze. Charley’s boasts a world-class wine list with nearly 1,000 selections and has earned accolades including Wine Spectator’s “Best of Award of Excellence,” DiRōNA, and Orlando Magazine’s “Best Steak House.” Charley’s Steak House delivers top-notch service and exceptional dining experiences—come taste the difference and discover why it's considered the #1 steakhouse in America.
A photo of The District Gastrobar restaurant
5. The District Gastrobar
3.7
Very Good(244)
££££
• American • Downtown Orlando
Booked 4 times today
The District GastroBar has an innovative design that starts in the restaurant's entrance, a well ­curated modern speak easy with a nostalgic vintage ambiance and an eclectic array of "one ­off" pieces of Prohibition and 1940 era inspired artwork. Walk past the restaurants front door, guests encounter a antique bronze tin ceiling wrapped around historic 1900 brick, custom vintage lighting, but only the adventurous will discover all that The District GastroBar has to offer. With a distinct dining room, grandiose bar layout, an open air patio and a women’s bathroom complete with a salon inspired feel and antique perfume bottles. The cuisine, much like the design, is intended to set a new course. Chef Lamond Cooper and menu creator Andre Walton have adapted to the new shared plate dining trend that has swept the nation, and with The District GastroBar menu, they have created waves on the food scene better known as GASTRONOMY!
A photo of The Old Jailhouse restaurant
6. The Old Jailhouse
4.6
Exceptional(718)
££££
• American • Sanford
Booked 12 times today
Coming Soon!
A photo of VINIA Wine & Kitchen restaurant
7. VINIA Wine & Kitchen
4.7
Exceptional(104)
££££
• Italian • Winter Park
Booked 6 times today
Recognized as one of the Most Romantic Restaurants in Orlando, VINIA Wine & Kitchen is a locally owned, family-run wine bar and restaurant in Historic Winter Park. Steps away from Park Avenue and Hannibal Square parking lot. Perfect for date night, girls' night, and private events, enjoy a complete wine-pairing dinner experience with a boutique wine list and European-style menu, accommodating all dietary preferences, including creative plant-based and gluten-free options.Embrace The VINIA Way of Life! Relax at the bar, outdoor seating, or cozy table. Enjoy small plates for Happy Hour, Live Music Thursdays, and 3-course dinner including wines, for $59!On select Spring, Fall, & Holiday dates, join THE VINIA TABLE, an elevated 5-course wine dinner experience offering both traditional and vegan menus.Founded in 2018, now proudly owned by Rafael and Marina Lima, carrying on the legacy, beloved recipes, and commitment to great wine, and food. Reservations recommended. Walk-ins welcome.
A photo of Chef's Table at the Edgewater restaurant
8. Chef's Table at the Edgewater
4.9
Exceptional(2781)
££££
• American • Winter Garden
Booked 7 times today
In historic downtown Winter Garden, a few miles from Orlando’s theme parks, an intimate gourmet dining experience awaits you. Local residents rave about it, and foodies come from all over to sample the superb cuisine and intimate service of The Chef's Table at the Edgewater. Our 3 Course Prix Fixe Dinner is priced at $74.99 per person, consists of 4 choices/course. Pricing may vary on holidays. Guests must be over the age of 8 to dine at the Chef's Table, which generally takes 2 hours.Brunch is now served on Sat & Sun at our Tasting Room. Recent awards include the Florida Trend Golden Spoon, Orlando Magazine Dining Awards, winning Best Restaurant, Best Kept Secret, Best Wine Pairing Dinner, Most Romantic Rendezvous, & Best Chef's Table. For diners wanting a more casual evening, our Tasting Room serves brunch, small plates, large plates & craft cocktails, and does not require a reservation.Group dining features dining areas for group sizes 10-60.
A photo of Blue Flame at The Daytona restaurant
9. Blue Flame at The Daytona
4.4
Awesome(298)
££££
• American • Daytona Beach
Booked 4 times today
Sip and savor in style at the Blue Flame bar, the ideal destination to unwind and mingle amongst the best brews and creative cocktails reflecting the historic excitement of racing.
A photo of Amare at Walt Disney World Swan Reserve restaurant
10. Amare at Walt Disney World Swan Reserve
4.7
Exceptional(723)
££££
• Mediterranean • Lake Buena Vista
Booked 16 times today
Amare, which means “to love”, is a casual upscale venue inspired by the tastes and cultures of the Mediterranean region. The menu focuses on highlighting fresh premium ingredients popular in the area, including a wide variety of seafood, citrus, olive oils, pasta and pitas.

See what locals rave about

From verified diners like you
From verified diners like you
  • ChelseaGold
    Orlando / Central Florida East •27 reviews
    5.0
    Dined 3 days ago
    10/10 experience, can’t wait to go back! My girlfriends and I met for a celebratory dinner and we all had a wonderful time. The food was INCREDIBLE, coursed out perfectly, cooked perfectly and with impeccable flavor profiles on every dish. The service was awesome as well! No water glass unfilled, silverware replaced and laid by course, and consistent check ins without being overbearing. We were there to celebrate the publishing of my first book and they brought out a special dessert AND a card signed (specifically about my book…not pre-signed!) by all the staff. That touch right there pushed the evening over from a wonderful night to a perfect one. Thank you all again!!
    More info
    The Chapman$$$$• Contemporary American• Winter Park
    •
    4.8
  • ashley
    Raleigh / Durham / Chapel Hill •1 review
    5.0
    Dined 4 days ago
    The service was top notch! Our server was fabulous and extremely attentive. The food was delicious and the filet, beef wellington and salmon were all cooked to perfection. The cheesecake infused with espresso and the molten lava cake were out of this world. Definitely one of the best restaurants I have dined in.
    More info
    KRES CHOPHOUSE$$$$• Steak• Downtown Orlando
    •
    4.9
  • Sherri
    Greater Boston •3 reviews
    5.0
    Dined on 26 May 2026
    Food and drinks were superb - only outdone by the top notch service. Will be back again!
    More info
    The Old Jailhouse$$$$• American• Sanford
    •
    4.6
  • MaudGold
    Orlando / Central Florida East •2 reviews
    5.0
    Dined on 16 May 2026
    We always enjoy going there with our little one. I had the short ribs for the first time with the alligot potatoes and it was truly delicious. The service was excellent. There was just a loud group right next to us swearing all the time which wasn’t the greatest. Once they left we were able to enjoy ourselves again
    More info
    Russell's on Lake Ivanhoe$$$$• Contemporary American• Downtown Orlando
    •
    4.5
  • Linda
    Orlando / Central Florida East •3 reviews
    5.0
    Dined on 17 Apr 2026
    This place never disappoints. We frequently go before Magic games and it’s always delicious. Owner is friendly and service is always good.
    More info
    The District Gastrobar$$$$• American• Downtown Orlando
    •
    3.7

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