Italian Restaurants in Winter Park


Select Local Merchants

  • Tolla's Italian Deli Cafe
    Chef and owner Gary Tolla selects dishes from a large rolodex of family Italian recipes to fill out the menu at Tolla’s Italian Restaurant. Veal and chicken receive the parmigiana, marsala, and piccata treatments, and raviolis are stuffed with cheese to create little pillowy pockets almost identical to actual dollhouse pillows. A selection of wine helps wash down hot and cold subs or pizzas concocted from shareable 12-inch disks or personal 10-inch crusts. On Friday and Saturday evenings, live entertainment—from bands to a Rat Pack balloon artist—entertains patrons inside the eatery.
    Read More
    240 N Pennsylvania Ave
    Winter Park, FL US
  • Pannullo's Italian Restaurant
    Stucco walls arranged to reveal the brick underneath frame tall, arched doorways and give Pannullo's Italian Restaurant the air of the old country. The Tuscan-style décor accents a menu of traditionally prepared veal, seafood, and chicken entrees, each doused in marinara, wine, or cream sauces. Beneath the awnings in the front of the restaurant, diners can enjoy al-fresco meals surrounded by wrought iron and leafy plants that have been trained not to beg for scraps.
    Read More
    216 S Park Ave.
    Winter Park, FL US
  • Pizzeria Valdiano
    Voted best pizza in town by the Orlando Sentinel for seven years in a row, Pizzeria Valdiano unleashes a welcome avalanche of dough, cheese, tomato paste, and freestyle-snowboarding cherry peppers upon the burgundy-boothed slopes of the restaurant’s interior. The pie-centric menu democratically offers a motorcade of non-pie starters such as fried mozzarella ($4.95) and garlic-bread parmigiana ($3.75) to take down those who lack the drive to take a piece of the cheesy disc. Try an artichoke-hearty pizza Fiorentina ($9.50 for 10", $16.95 for 16"), a peppery pizza piccante ($9.50/$16.95), or a pizza stella ($10.95/$17.95) with melted mozzarella, eggplant, and feta cheese.
    Read More
    510 N Orlando Ave
    Winter Park, FL US
  • Papa Joes of Winter Park
    We are a full service Italian restaurant serving fresh salad, delicious pasta, and outstanding pizza.
    Read More
    501 N Orlando Ave
    Winter Park, FL US
  • Olive Garden
    For spaghetti and meatballs that tug at the heartstrings, Olive Garden creates a warm atmosphere perfect for two. Life is all about choices, and they are not limited here with plenty of gluten-free and low-fat dishes. Take a peek at the drink menu here, and make sure to sample something off the list. Olive Garden is well-known for being able to seat large parties. Casual dining at its best, Olive Garden customers are free to enjoy themselves in jeans and a T-shirt. If you need to get somewhere fast, the restaurant also serves up grub to go. Cyclists are in luck. Olive Garden provides bike parking. Meals at Olive Garden are moderately priced — most diners spend about $30 per person.
    Read More
    665 N Orlando Ave
    Winter Park, FL US
  • Prato
    For pasta with a twist, try Prato, a stylish spot for Italian cuisine. Enjoy a low-fat or gluten-free meal at Prato, a local favorite. Enjoy a drink with your dinner — Prato has a full bar to serve up a glass of wine, beer, or more. The patio tables outside of Prato are the perfect spot for a summer meal. It doesn't get much more laid-back than Prato, so dress for comfort when you come. Always five minutes behind schedule? Pick up your food to go instead. Drivers heading toward Prato's N Park Ave residence will be pleased to know that this location offers valet parking. Prato offers safe bike parking outside. Prepare to spend about $30 per person when dining at Prato.
    Read More
    124 N Park Ave
    Winter Park, FL US

Groupon Guide