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Best Historic Restaurants in Kissimmee

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21 restaurants available nearby

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A photo of Charley’s Steak House-Orlando, FL restaurant
1. Charley’s Steak House-Orlando, FL
4.8
Exceptional(6790)
$$$$
• Steakhouse • I Drive / Sand Lake
Booked 46 times today
Charley’s Steak House on Orlando’s iconic International Drive has been a Florida favorite since 1992, proudly owned by the Woodsby family. Specializing in USDA Prime and Choice Angus beef from three-year-old steers, each steak is aged 4–6 weeks, hand-cut daily by the management team, and flame-grilled over a 1,200º Florida citrus and oak wood fire for unmatched flavor. The ambiance is upscale yet inviting, with rich wood accents and a lively energy. Guests can also enjoy outdoor dining on the spacious patio, perfect for soaking in the Florida breeze. Charley’s boasts a world-class wine list with nearly 1,000 selections and has earned accolades including Wine Spectator’s “Best of Award of Excellence,” DiRōNA, and Orlando Magazine’s “Best Steak House.” Charley’s Steak House delivers top-notch service and exceptional dining experiences—come taste the difference and discover why it's considered the #1 steakhouse in America.
A photo of Il Mulino New York Trattoria - Orlando at the Walt Disney World Swan Resort restaurant
2. Il Mulino New York Trattoria - Orlando at the Walt Disney World Swan Resort
4.4
Awesome(3595)
$$$$
• Italian • Lake Buena Vista
Booked 56 times today
The acclaimed Il Mulino New York Trattoria offers its superior signature dining experience in a relaxed and vibrant setting. Guests can enjoy fragrant wood-fired pizzas, fresh fish, chicken, pastas and meats, all bursting with hearty blends of seasonal ingredients drawn from the Abruzzi region of Italy. Join us at Trattoria Il Mulino for an exquisite culinary experience where each bite evokes the skill, dedication and passion that has made Il Mulino New York an international icon for over 35 years. This restaurant is one of our Signature Dining experiences. Guests are expected to dress accordingly in attire that respects the restaurant's sophisticated and upscale aesthetic. Clothing should be clean, neat and in good condition, free from offensive language and/or graphics. Please no swimwear.
A photo of The Old Jailhouse restaurant
3. The Old Jailhouse
4.7
Exceptional(724)
$$$$
• American • Sanford
Booked 14 times today
Coming Soon!
A photo of KRES CHOPHOUSE restaurant
4. KRES CHOPHOUSE
4.9
Exceptional(5691)
$$$$
• Steak • Downtown Orlando
Booked 64 times today
The present and past pair beautifully at Kres Chophouse, a classic, top tier Steakhouse with a modern eclectic flair. This premier Steakhouse embodies the heart of Orlando's historic district, featuring chic and elegant décor within the striking architecture of a 1930's landmark. A thoughtful layout with luxurious banquettes and private dining options create an intimate dining atmosphere.Kres Chophouse specializes in house aged, hand cut prime steaks and the freshest seafood, sourcing quality ingredients that emphasize authenticity over pretension. The full bar boasts a diversified and well-curated wine list as original as the art on the walls, with a weeknight happy hour featuring half priced appetizers at the bar.Easy valet parking and the bustling nightlife of Orlando's legendary Church Street create an extraordinary dining experience for a night on the town!
A photo of Amare at Walt Disney World Swan Reserve restaurant
5. Amare at Walt Disney World Swan Reserve
4.6
Exceptional(740)
$$$$
• Mediterranean • Lake Buena Vista
Booked 12 times today
Amare, which means “to love”, is a casual upscale venue inspired by the tastes and cultures of the Mediterranean region. The menu focuses on highlighting fresh premium ingredients popular in the area, including a wide variety of seafood, citrus, olive oils, pasta and pitas.
A photo of The Chapman restaurant
6. The Chapman
4.8
Exceptional(761)
$$$$
• Contemporary American • Winter Park
Booked 51 times today
Nestled in the heart of Winter Park, The Chapman enjoys a prime location on the charming and vibrant Park Avenue, surrounded by the city’s rich history, upscale boutiques, and picturesque lakes. The Chapman brings a fresh perspective to fine drinking and dining, where discovery meets comfort and indulgence. Warm, stylish, and artful with a distinctive Winter Park Florida look and feel, we invite you to celebrate the best of Florida while our hospitable team strives to pamper you and make every gathering truly memorable.
A photo of Chef's Table at the Edgewater restaurant
7. Chef's Table at the Edgewater
4.9
Exceptional(2784)
$$$$
• American • Winter Garden
Booked 12 times today
In historic downtown Winter Garden, a few miles from Orlando’s theme parks, an intimate gourmet dining experience awaits you. Local residents rave about it, and foodies come from all over to sample the superb cuisine and intimate service of The Chef's Table at the Edgewater. Our 3 Course Prix Fixe Dinner is priced at $74.99 per person, consists of 4 choices/course. Pricing may vary on holidays. Guests must be over the age of 8 to dine at the Chef's Table, which generally takes 2 hours.Brunch is now served on Sat & Sun at our Tasting Room. Recent awards include the Florida Trend Golden Spoon, Orlando Magazine Dining Awards, winning Best Restaurant, Best Kept Secret, Best Wine Pairing Dinner, Most Romantic Rendezvous, & Best Chef's Table. For diners wanting a more casual evening, our Tasting Room serves brunch, small plates, large plates & craft cocktails, and does not require a reservation.Group dining features dining areas for group sizes 10-60.
A photo of Russell's on Lake Ivanhoe restaurant
8. Russell's on Lake Ivanhoe
4.4
Awesome(1432)
$$$$
• Contemporary American • Downtown Orlando
Booked 17 times today
Located on the historic Lake Ivanhoe, Russell's offers an upscale casual dining restaurant and bar featuring an innovative and fresh menu, all with an amazing view and atmosphere.Chef Emmanual Clement has created a varied and exciting menu based on his international experience.Some of our favorite suggestions include:Artisan Charcuterie Board, Roasted Beets & Burrata Napoleon & Octopus Escabeche (we cure our own meats)Entrees: Grilled Swordfish with Sorrel Sauce, Crispy Duck Confit & Tenderloin Au Poivre (all sauces made fresh in house)Desserts: White Chocolate Bread Pudding with Whiskey Sauce & Cranberry Crème Brulée (all our desserts are made in house)Awards:Top Tables 2020Best Burger 2021 Orlando Sentinel Foodie AwardBest Ambiance; Editor's Choice Orlando, The City's MagazineBest Brunch: Readers' Choice Orlando, The City's MagazineIf you any dietary requirements just let us know ahead of time and we will try and accommodate you.See you soon!
A photo of Arabellas Italian Ristorante restaurant
9. Arabellas Italian Ristorante
4.6
Exceptional(1729)
$$$$
• Italian • Winter Haven
Booked 17 times today
Welcome to Arabellas Ristorante, located in Times Square at the heart of historic downtown Winter Haven. Arabellas offers an elevated Italian dining experience where timeless culinary tradition meets refined elegance. Chef Jay’s thoughtfully curated menus showcase the finest ingredients, artfully prepared and beautifully presented in an intimate, sophisticated setting. Guests return time and again for our signature dish, Vitella di Arabellas, a house favorite that perfectly reflects our dedication to classic Italian excellence.Proudly recognized as a 2025 OpenTable Diners’ Choice Award winner, Arabellas is known for its romantic ambiance, attentive service, and exceptional attention to detail — creating memorable evenings for celebrations, special occasions, and elegant nights out.Enjoy live piano entertainment every evening, Monday through Saturday, from open to close, enhancing the warm and luxurious atmosphere.
A photo of The District Gastrobar restaurant
10. The District Gastrobar
3.3
Good(248)
$$$$
• 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!

See what locals rave about

From verified diners like you
From verified diners like you
  • Paula
    Orlando / Central Florida East •2 reviews
    5.0
    Dined 2 days ago
    Charley’s Steakhouse has been our favorite Orlando restaurant since the 1980’s starting with the OBT location and now the Charley’s on International Drive. Tara, our server was exceptional and made our dinner special. Old school ambiance combined with exception service and food ensures a memorable dining experience. The steaks are always cooked to perfection and the Fried Shrimp is an item you cannot find anywhere. Trust me I have tried to find Shrimp but Charley’s fresh shrimp and timeless recipe is outstanding. Thank you Charley’s and Talk of the Town for a great evening.
    More info
    Charley’s Steak House-Orlando, FL$$$$• Steakhouse• I Drive / Sand Lake
    •
    4.8
  • Martin
    Lancashire •2 reviews
    5.0
    Dined 3 days ago
    Staff exceptional from victor on welcome desk to Steven & Jamie our servers. Great job chefs
    More info
    Il Mulino New York Trattoria - Orlando at the Walt Disney World Swan Resort$$$$• Italian• Lake Buena Vista
    •
    4.4
  • Lauren
    Orlando / Central Florida East •7 reviews
    5.0
    Dined on Jul 3, 2026
    I took my 6 year old daughter here to have a special mommy-daughter fancy dinner night and everything was amazing! Everybody was so sweet to her and helped to make it a very special evening. From the hostesses to the server and manager and even the chef……they all made her feel like a princess. Chef Mary made her a special dinner and dessert that was delicious and of the very best quality. Kres remains the best restaurant in Orlando, capable of handling business dinner and date nights and diners with the most distinguished of tastes……..children :) 5 stars across the board as usual!
    More info
    KRES CHOPHOUSE$$$$• Steak• Downtown Orlando
    •
    4.9
  • sarah
    New York City •2 reviews
    5.0
    Dined on Jun 30, 2026
    We had the most wonderful dinner. Shannon’s service was exemplary. She made the meal memorable and special. Highly recommended!
    More info
    Amare at Walt Disney World Swan Reserve$$$$• Mediterranean• Lake Buena Vista
    •
    4.6
  • Joel
    Orlando / Central Florida East •14 reviews
    4.0
    Dined on Jun 20, 2026
    Food was nice and hot, tasted good and was plentiful.
    More info
    The Old Jailhouse$$$$• American• Sanford
    •
    4.7

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