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Best Fun Restaurants in Winter Garden

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267 restaurants available nearby

A photo of Matthew's Steakhouse restaurant
4.6
Exceptional(193)
Price: Very Expensive
• Steakhouse • Winter Garden
Booked 20 times today
ELEVATED DINING EXPERIENCE. Discover the unique culinary experience of Matthews Steakhouse, where locally-sourced ingredients meet exceptional service. Our dishes are not only delicious, but also nutritious! Come and join us for an unforgettable dining experience in Downtown Winter Garden. Our sommelier Eddie Gaunt is always on hand to help you select the perfect wine pairing for your meal.​Book Your Dining Experience: Reserve Your Table Today at Our Family Owned and Operated Reservation-Only Restaurant.
A photo of X Sushi restaurant
4.9
Exceptional(36)
Price: Expensive
• Sushi • Winter Garden
Booked 6 times today
The best Japanese cuisine restaurant in Orlando.A gastronomic experience elevated to each piece.Come and try a symphony of refined flavors! Explore unparalleled flavors in our fresh and exclusive sushi.
A photo of The Attic Door Bistro restaurant
4.4
Awesome(73)
Price: Expensive
• Bistro • Winter Garden
Booked 6 times today
The Attic Door in downtown Winter Garden is a charming neighborhood bistro with an eclectic atmosphere. The menu choices provide a delicious variety of small plates, sliders, dinner specials, and dessert. Great choices for wine or craft beer to pair with the savory menu and talented local musicians add to this popular destination. Our food is sourced locally whenever possible, by Chef David Lampman. Our Afternoon Tea Experience provides tiered plates with scones, clotted cream, finger sandwiches, savories, dessert and a premium pot of loose leaf tea. Also a perfect setting for showers and birthday celebrations. Our venue is perfect for large groups wanting to host a private event in our entire space as well.
A photo of The Boathouse restaurant
4.7
Exceptional(15572)
Price: Expensive
• Seafood • Lake Buena Vista
Booked 255 times today
The Boathouse is a fun-filled, waterfront dining experience. It's not just about the food, but the overall experience. From live music and guided Amphicar rides to a dreamy setting with floating artwork from the 30's, 40's & 50's, this place is a treat for all senses. The reviews are full of praises for its 'fun atmosphere', 'vibrant' ambiance, and 'great food'. The service is exceptional, and the overall experience is a 'great fun'!
A photo of The Cake Bake Shop at Disney's BoardWalk restaurant
4.6
Exceptional(540)
Price: Expensive
• American • Bay Lake
Booked 268 times today
Discover this new restaurant and bakery with a whimsical atmosphere that complements the idyllic charm of Disney’s BoardWalk. Discover an array of sensational dishes and desserts—along with afternoon tea—in this beautiful dining room and bar. Upon entering the bakery, you’ll find counters lined with handmade cakes that are one-of-a-kind in beauty and taste, attractively displayed on French porcelain platters topped with glass domes.
A photo of Summer House on the Lake - Disney Springs restaurant
4.7
Exceptional(3042)
Price: Moderate
• American • Lake Buena Vista
Booked 342 times today
Booking a table for more than 6 people? Please reach out to our parties team at summerhouseorlandoparties@lettuce.com or by calling 407-598-8645, Ext. 2. Due to the limited number of tables that can accommodate 7+ guests, we reserve these spots for private groups to ensure the best experience. If your group is able to split up into multiple tables, you are able to make a reservation through OpenTable. We cannot guarantee that your party would be sat all together. The team will do their best to accommodate. Discover Summer House on the Lake at Disney Springs in Orlando, FL. Chef Ben Goodnick brings you a California-inspired menu made with simple, sustainable ingredients, offering artisanal pizzas, pasta, fresh salads, sandwiches, and more. Make a reservation to enjoy seasonal cocktails and the best wines from California, including the signature Summer House Rosé. Choose from indoor or outdoor seating with direct lake views.
A photo of Cafe Tu Tu Tango - Orlando restaurant
4.7
Exceptional(6995)
Price: Moderate
• Tapas / Small Plates • I Drive / Sand Lake
Booked 114 times today
For over 30 years, Café Tu Tu Tango has been the go-to spot on Orlando's International Drive for food, art, and fun. Featuring a tapas-style menu packed with shareable small plates, guests can enjoy live entertainment while resident artists create right before their eyes. Sip on art-inspired craft cocktails, signature sangrias, and more from the drink menu. Open daily for lunch and dinner, with bottomless brunch available every Friday through Sunday.
A photo of Raglan Road Irish Pub restaurant
4.8
Exceptional(12476)
Price: Moderate
• Irish • Lake Buena Vista
Booked 108 times today
Raglan Road Irish Pub is a fun place to be with its lively atmosphere and great entertainment. As one reviewer put it, the 'traditional music & dancing make for an amazing ambiance & a unique experience.' Another reviewer noted that the 'Irish music and dancers displayed incredible talent and energy.' Plus, the food is delicious with 'exciting house bands imported from Ireland' and 'surprising diversity on the menu.' It's a great place to eat and be entertained at the same time!
A photo of Hard Rock Cafe - Orlando restaurant
4.4
Awesome(5220)
Price: Moderate
• American • I Drive / Sand Lake
Booked 156 times today
Hard Rock Cafe is a global phenomenon with 185 cafes that are visited by nearly 80 million guests each year. The first Hard Rock Cafe opened on June 14, 1971, in London, England, and from there the brand has expanded to major cities and exotic locations around the world. Hard Rock Cafe is the world's largest location!
A photo of JoJo's Shake Bar - Orlando restaurant
4.1
Excellent(379)
Price: Moderate
• American • I Drive / Sand Lake
Booked 27 times today
JoJo's Shake Bar in Orlando is a blast! It's known for its fun, energetic ambiance that's perfect for family affairs, first dates, and casual nights out. As one reviewer put it, 'The aesthetic in this place is amazing. Food, drinks, music all were a vibe.' Another said, 'Such a fun place, totally great vibe, delicious food and drinks, don't skip the shakes!'. Plus, the menu offers a wide variety of creative desserts and elevated diner favorites. So, if you're looking for a vibrant dining experience, JoJo's Shake Bar is the place to be!
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you
From verified diners like you
  • Nichole
    Los Angeles •1 review
    5.0
    Dined 1 day ago
    It was a wonderful experience. The food was delicious and the waitress was lovely. I just wish it wasn’t so loud. But it was a very busy place for a reason, It is a great place.
    More info
    The BoathousePrice: Expensive• Seafood• Lake Buena Vista
    4.7
  • Shaina
    Indiana •4 reviews
    5.0
    Dined 1 day ago
    Our experience was absolutely amazing! Being from Indy, we already knew how wonderful Cake Bake was, but visiting the Orlando location exceeded all our expectations. From the sparkling lights outside to the warm and helpful staff, every detail was magical. Our server (Julian M) went above and beyond, making each moment extra special. The Indiana touches, like the Cake Bake Lemon Shakeup and Gwendolyn’s Cosmopolitan, brought a nostalgic charm to the experience. The food was phenomenal! The crab cake was exceptional—packed with huge chunks of crab and no filler. The pomme frites with the garlicky aioli were irresistible, and the po’ boy was both massive and delicious. We ended with the chocolate peanut butter pie, which was absolutely divine. The perfect finale was the Glitter Wish—such a whimsical and memorable touch! We never felt rushed, and the entire experience felt like an extraordinary event. Cake Bake is a true gem and 1000% deserves a spot in Disney. It was worth every second, and we’ll cherish this unforgettable experience!
    More info
    The Cake Bake Shop at Disney's BoardWalkPrice: Expensive• American• Bay Lake
    4.6
  • Lisa
    South Carolina •11 reviews
    5.0
    Dined 5 days ago
    We went to Matthew’s for our wedding anniversary celebration. The food was excellent, service was good, nice ambiance too. We had a table for 2 that was large, and the restaurant was very busy, so it was hard to talk. Next time we will request a booth. Highly recommend the lobster bisque and filet mignon. Delicious! Owner was present and she was very attentive and personable. We will be back!
    More info
    Matthew's SteakhousePrice: Very Expensive• Steakhouse• Winter Garden
    4.6
  • CarolinaVIP
    Orlando / Central Florida East •19 reviews
    5.0
    Dined 7 days ago
    I love this place! It’s my second time there. You need to try the Salmon Carpaccio and the Otsu sushi. The service it’s amazing they explain the menu and give you a lot of recommendations. The place itself it’s really nice inside.
    More info
    X SushiPrice: Expensive• Sushi• Winter Garden
    4.9
  • Ed
    Tampa / Central Florida West •1 review
    5.0
    Dined on Dec 20, 2024
    Mgr Kim very aware and accommodating of our food needs. She personally analyzed the menu and suggested food choices. Addison was an attentive and cheerful server the food was excellent and wellprepared. A great experience for my wife and I.
    More info
    The Attic Door BistroPrice: Expensive• Bistro• Winter Garden
    4.4
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