By Kate Cohen
Updated July 14, 2026
It’s that time of year again! Are you ready to join us at Harry’s Poolside Bar & Grill for Magical Dining 2026?
Stop by and enjoy our special three-course prix-fixe Magical Dining menu anytime between August 15 and September 30.
For the awesome price of $40 per person, this experience allows you to curate a delicious meal full of bold tropical flavors and fresh ingredients. And you’ll be supporting an Orlando non-profit.
Here is a look at what you can expect from your Magical Dining dinner date at Harry’s Poolside Bar & Grill.
Key Takeaways
- Starters
- Entrees
- Desserts
- Support our Local Orlando Community with Magical Dining
- Enjoy a Refreshing and Relaxing Three-Course Meal at Harry’s Poolside Bar & Grill
Starters
Treat your taste buds to a variety of exciting flavors with one of four appetizer options.
The Mexican Street Corn Dip is a twist on a street food favorite. This zesty dip blends juicy sweet corn with tangy tajin spices, lime, and cream cheese. Scoop up every morsel with a side of colorful tortilla chips.
Feel like starting your Magical Dining experience with some seafood? The Cayman Island Calamari, breaded in panko, is perfectly crispy and served with a flavorful aioli.
The Oh My Gorgonzola Dip is a Harry’s classic app, made with caramelized onions, fresh garlic, roasted tomatoes, and artichokes. It’s served with baked roti bread, the perfect vessel for this popular starter dip.
Or start simple yet flavorful with Harry’s Salad. It combines mixed baby greens and ripe fresh berries with balsamic vinaigrette.
Entrees
The main course presents an array of delicious options from which to choose.
If you’re craving steak, the Grilled New York Steak is a great choice.
This thick cut of meat is marinated in chimichurri for an extra herby tang. Sauteed mushrooms and onions finished with a rich gorgonzola sauce add layers of flavor stacked on the steak.
The steak is served with creamy mashed potatoes and sweet plantains, creating Harry’s signature tropical twist.
The Jamaican Jambalaya will warm your soul with its blend of tender chicken, plump shrimp, spicy chorizo, vegetables, and rice and beans. A zesty Creole sauce punches up the flavor.
Mojo Chicken & Gambas al Ajillo is a dish of garlicky mojo marinated chicken breast and juicy jumbo shrimp. Served with queso fresco, tropical salsa, and Mamposteao rice (Puerto Rican fried rice), this entree is Harry’s flavorful version of a poolside surf and turf.
Last but certainly not least, the Ropa Vieja, a Cuban classic. Braised beef is stewed wtih onions, peppers, and tomatoes in a red onion mojo sauce. This final main course option is served with Mamposteao rice and fried yucca.
Desserts
Last but never least is dessert, and our Magical Dining menu truly delivers when it comes to sweet treats.
The sponge cake in the Tres Leches martini is served not shaken, not stirred, but soaked in three different kinds of milk. The serving is topped off with fresh whipped cream, colorful berries, and pistachios for an added crunch.
If you’re craving cocoa after your first two dishes, the Chocolate Flan is for you. Delight in this chocolatey twist on a classic Latin American custard. It’s topped with fresh berries, whipped cream, and a caramel drizzle.
Indulge in the richness of NY Style Cheesecake, a traditionally prepared classic with a sweet sponge cake crust.
Finally, crunch into Taza De Churro for a sweetly satisfying end to any meal. These crispy cinnamon-sugar-coated churros are complimented with Dulce De Leche Gelato and a side of chocolate sauce.
Support our Local Orlando Community with Magical Dining
When you participate in Magical Dining, not only are you getting an incredible three-course meal for an amazing price; you’re also helping to support local Orlando nonprofits.
For 21 years, Magical Dining has partnered with Central Florida restaurants to offer exclusive prix-fixe menus. For every Magical Dining menu ordered, the organization will donate up to $2 to deserving local nonprofits.
This year’s nonprofit recipients are Children’s Safety Village, The Daily Bread, Nathaniel’s Hope, NextStep Orlando, The Nurture Place, and Victim Service Center of Central Florida.
You can support these amazing causes simply by dining at Harry’s Poolside Bar & Grill during Magical Dining 2026.
Enjoy a Refreshing and Relaxing Three-Course Meal at Harry’s Poolside Bar & Grill
There’s nothing better than a day lounging by the pool in sunny Orlando, and the vacay vibes don’t have to end when it’s time for dinner.
Harry’s Poolside Bar & Grill at Rosen Centre keeps things relaxed and refreshed with Caribbean-Cuban inspired cuisine and a light and airy ambiance.
Whether you’re dining indoors in our chic, contemporary restaurant or al fresco on the patio, you’ll enjoy views of the scenic outdoor pool deck and swaying palm trees.
At Harry’s Poolside Bar & Grill, we are waiting for you to join us with open arms and a tropical drink in hand. Bring your appetite and get ready to experience fresh new flavors and a contemporary poolside ambiance.
If you’re ready to make your reservation, you can do so on OpenTable or by calling (407) 996-1787.
