29 Best Italian Restaurants near Winter Garden

“My favorite restaurant in Winter Garden. Decided to do Italian for Thanksgiving and it was outstanding. My favorite is their Pork Osso Bucco and they did not disappoint. Service and owners are always on point. Thank you for enjoying my first Thanksgiving being waited on. Always recommend this place, never a bad meal. Thank you Dorina“

“Huge RAVE for La Piccolina - Winter Garden. We went to celebrate my father’s birthday and everything was wonderful. The food was delicious, so flavorful and generous portions! On top of our delicious meals the service was excellent! They went above and beyond, surprised my daughter with a fun make her own pizza, which was so fun and a sweet surprise. This place is authentic and caters to hospitality! Thank you for making our dining experience so wonderful! We can’t wait to come back.“

“We were a group of 10. Reservations honored. Antonio introduced himself and was excellent! Service was impeccable. Appetizers were brought to the table by house choice. Food choices was something for everyone. All dinners were served at the same time and to everyone’s liking. The pasta was truly homemade.Our lemonciello spritz was made just right. A requested dessert was no longer available and was surprised with a special substitute on the house. A total recommendation. Kudos to the owner for a fabulous experience. Thank you“

“Sue and I have not been to this place since they converted to sit-down and order. Finally joining the real restaurant world. We have eaten here about 20 times in the last few years and have always enjoyed the food, but felt strange with the get-your-own-drink aspect of it. Anyways, we are seated at our favorite booth, Perry Como, Elvis, Dean Martin, and Sinatra (the usual suspects) crooning at a comfortable level, with decent speakers. Oscar greeted us and took our drinks order, leaving a couple of rather impressive menus with us. We spent some time looking at the menu, as the format has changed somewhat. I ordered the shrimp marsala on linguine, Sue ordered the same on some other pasta noodle (You choose). After a reasonable interval, our food arrived. 2 huge bowls of deliciousness thick enough that it could have been called a stew. Lrt me tell you, I've been to restaurants that the orders contained little meat, little mushrooms, and a LOT of broth. Not here! These bowls were crammed with a ton of food. Shrimp, portobella mushrooms and pasta that was not overcooked. I gotta tell you, Sue and I dine out a LOT...various venues all over WG/Ocoee/Windermere/Clermont. This was probably the finest meal I ever had. The improvements the restaurant made are A+ Definitely worth dropping a hundy on.“

“The best pasta I have ever tried! On top of that it’s the customer service you receive whenever you make an order or go to the markets. A company with true customer loyalty with the best fresh pasta at its heart.“

“Local Gem We live a 15 minute stroll from Mangoni's Italian Market, but at "feels like" temps hovering around 105°, strolling to lunch hasn't been as attractive ? Sunday, hubby wanted a relaxing lunch with sangria! So, we drove (& charged our EV in the parking garage). We had the entire patio to ourselves, as diners likely expected unbearable heat. Mangoni's pergola and great ceiling fans made patio dining the experience we wanted---even when the afternoon storm blew up from the west, we were protected from rain. We enjoyed our favorite, GF goat cheese pizza, with our sangria. Unlike most places, Mangoni's GF crust is an excellent, thin cauliflower crust. And, it’s not an upcharge. We also enjoyed meeting Georgia, the regional manager, who chatted with us about the social hour (11-6pm weekdays). She made a GF garlicky cheesy Flatbread for us to try--now we have more reason to stroll (or drive) over! Oh, and take away is a frequent option. Really, Mangoni's is a local gem.“

“Great service and food😋 One of my favorite place🙌😋“

“We always enjoy lunch at this I-Drive location. The food is delicious and May, our server, is always amazing. May is extremely attentive and personable. Good job Carrabbas and May! Can’t wait to go back.“

“Great food and great service“

“I recently had the pleasure of dining at Maggiano's Little Italy in Orlando on International Drive and it was an experience worth sharing. From the moment we walked in, we were greeted warmly by the hostess, who promptly seated us at a cozy table that perfectly set the tone for the evening. The waitstaff was exceptional—attentive, friendly, and knowledgeable. They made sure our glasses were never empty and checked in just the right amount to ensure we had everything we needed without being intrusive. For the main course, we chose the Chicken Parmesan, which was cooked to perfection with a crispy exterior and tender, juicy chicken inside. The pasta was al dente, and the meat sauce was rich and savory. It was really enough for two people to share. To top it all off, they brought two plates of their famous lemon cookies to our table, to celebrate our third anniversary. Overall, our experience at Maggiano's was nothing short of excellent. The combination of outstanding service, a welcoming atmosphere, and delicious food made for a memorable evening. I highly recommend Maggiano's for anyone looking to enjoy a wonderful Italian meal with top-notch service.“

“The People are very nice and give great customers service!!! Pedro was cool when I ordered my food he make sure it was correct and fresh before I left cause it took me a little longer to pick up..and I appreciate that. I would recommend them to anyone... Stop by and get one of the best pizzas in Orlando FL“

“Visited Orlando for the weekend golfing at Bay Hill. Fresco's was recommended by the folks at the Lodge. Glad we stopped in for dinner. The food is excellent. It will be my goto on future Orlando visits.“

“Still one of my favorites. An old line Italian spot with requisite adornment, which though a bit threadbare, still evokes the full throated enthusiasm for classic service and cuisine. The food remains fantastic — the best Caesar salad after even all these years of making it the same way, meatballs so tender you'd think you were eating tofu, and carefully cooked (not overcooked mind you) seafoods. I wish I had the appetite to have the veal chop and more pastas.“

“We had an absolutely wonderful evening at Vincenzo's, and honestly, they got everything right. From the moment we walked in, the atmosphere felt warm and inviting. The lighting was spot-on — soft, flattering, without being too dim. The place was impeccably clean, from the spotless tables to the sparkling glasses and plates. You wouldn't believe how often restaurants overlook this basic detail, but at Vincenzo's, it's clearly a priority. Nothing kills your appetite faster than a dirty glass or plate — and we didn't have to worry about that here for even a second. Vincenzo himself was incredibly hospitable and gracious, making us feel like valued guests right from the start. And then there's Christina, the bartender — she suggested the perfect drink, listened carefully to my preferences, and customized it beautifully by omitting the elements I wasn't fond of. Such thoughtful service! The food was outstanding, and it's clear the chef is a major force behind the magic here. Every bite reflected skill, passion, and a deep respect for authentic Italian flavors — the kind of talent that turns good dishes into unforgettable ones. My husband ordered the risotto with mussels, and it was rich, creamy, perfectly cooked, and loaded with fresh seafood flavor. The portion was generous yet refined. I went with the Butternut Squash Ravioli featuring porcini mushrooms, sage, and a drizzle of truffle oil — and wow, what a dish! The ravioli were delicate, the filling sweet and earthy, and the sauce was pure magic. Beautifully plated and perfectly portioned — nothing overwhelming, just pure satisfaction. The prices were very fair — they reflect the high level of the dining experience without feeling over-the-top. You really get what you pay for here, and then some. If you're looking for authentic Italian food, genuine hospitality, and an evening that just feels special, Vincenzo's is the place. We're in the area on vacation, but I'd happily move here for the food at Vincenzo's! We can't wait to go back!“

“So I went to this location for the first time last week. We went after being at a theme park. First I'd like to mention this store is huge, very clean and organized. The host sat us rather quick being be had a big party. The server didn't show up for a few minutes, not too long really, but before it became an issue the floor managers had multiple people at our table to get our orders started. Once our server arrived I could tell her was overwhelmed but not rude. I watched him at his other tables, they were all big groups. Another manager came to check in on us to see if we were ok. There was a highlight to our night. A young lady that helped while she also had her own tables. I can't remember her name but she was very helpful and saw the importance of helping her coworker who was in the weeds. This location has great leadership and it shows through their staff. I highly recommend this location in a busy area of I Drive.“

“Peperoncino’s was absolutely amazing! The menu offered such a fantastic variety, and every dish was cooked to perfection. The desserts were a true delight, and the service couldn’t have been better. Our server, Daniel, was a joy—his menu descriptions were spot on and made the experience even more enjoyable. We can’t wait to come back, and I highly recommend you visit too!“

“Always a good classic wherever I go“

“Amazing food and service! I real gem to have here in Windermere!“

“Best eggplant parm I've ever had. Castello's is my new favorite restaurant. The young man who waited on us and the female chef were very polite and thanked us for coming in.“

“Amazing setting, music, and food. Everything is very presentable, and fresh.“

“I meant my five other girlfriends for dinner before a movie. The server was fabulous. Made wonderful recommendations and got us out in time for our movie. I had the sirloin which was delicious and we ordered a white pizza as an appetizer which was spectacular. My friend ordered the meatballs, which were super big and stuffed with cheese. So delicious wonderful restaurant we go there very often.“

“As someone who doesn’t take Italian food lightly, I walked in skeptical. I’ve spent years in Italy and my family are immigrants.
This place completely surprised me.
From the first bite, it felt like home. But what truly transported me were the live performances — the accordionist and vocalists moved through the room, taking requests and singing with such authenticity and heart that I found myself in tears. For a moment, I wasn’t in a restaurant — I was back in my grandparents’ home decades ago, surrounded by music, warmth, and love.
I left feeling full in every sense of the word — in my stomach and in my spirit.
A true hidden gem.“

“Food is good BUT there’s nothing more frustrating than trying to enjoy a quiet dinner with my husband only to have it interrupted by one of your servers loudly sharing her entire life story with the guests at the table next to us. Throughout our meal, we couldn’t help but overhear her talking about being a stay-at-home mom, her breakup, living with her mother, receiving an allowance, and even details about her father in Tennessee. These are not topics diners should be exposed to while trying to enjoy a meal. By the time I realized the conversation wasn’t ending anytime soon, I asked for my food to be boxed just so I could leave and have some peace. It was disappointing and unprofessional. I hope management addresses this, as staff should remain attentive and discreet so guests can enjoy their dining experience without hearing personal stories from the next table.“

“We had a celebration for my folks’ 50th anniversary here and it was so great. We really enjoyed the food and the staff were some of the kindest people I’ve ever had the pleasure of meeting.“

“Their are clearly mark take out and delivery. Do you feel the same way when you go papa johns or Dominos and there is no sitting.“

“Rene was wonderful!! He was polite, attentive without repeatedly interrupting our conversation. The food was delicious and the atmosphere was the perfect mix of a little bit casual and a little bit dressy. It really immersed us in the classic Italian feel.“

“Absolutely great food. Had pizza one night that was very good and the BBQ burger was AMAZING! Good drinks and the staff was phenomenal. Ray and Manny are the best! Highly recommend it. Tons of choices and the bar area is great for socializing or watching the game.“

“Very welcome and friendly manager and servers. The food was super italiono delicious. 👍🏻 from Thai fellows here.“

“Love this place… perfect combination of atmosphere and great food.“