By Kate Cohen
March 9, 2026
Travelers from around the world know Rosen Plaza as a beautiful, welcoming hotel in Orlando, conveniently located near the city’s most prized attractions.
Providing clean and comfortable accommodations to valued guests is the lifeblood of this beloved hotel, but its hidden gem restaurants create a well-rounded sense of hospitality for all visitors.
Whether you’re staying at the hotel as an overnight guest or simply looking for a meal that transcends the norm of “hotel food,” you’re sure to have a memorable dining experience at one of these Rosen Plaza restaurants.
Here’s a look at our signature dining establishments that are loved by travelers and locals alike.
Key Takeaways
- Jack’s Place: Where Dining Meets Originality
- ’39 Poolside Bar & Grill: Sips, Snacks, and Sunshine
- Café Matisse: The Heart of Rosen Plaza’s Breakfast Scene
- Lite Bite Express: Quick Eats Without Compromise
- Smoooth Java: Caffeinate and Rejuvenate
- Enjoy Breakfast, Lunch, and Dinner at Our Rosen Plaza Restaurants
Jack’s Place: Where Fine Dining Meets Originality
A Culinary Experience with Character
Just off the Rosen Plaza lobby, you’ll find Jack’s Place, the hotel’s signature steakhouse.
Upon first glance, you may note the cozy atmosphere with glowing amber lighting and pristine white table linens.
You’ll then notice the walls lined with framed hand-drawn caricatures of famed celebrities, politicians, and historic figures.
This one-of-a-kind art collection was created by Jack Rosen, the father of Rosen Hotels & Resorts founder, Harris Rosen.
In the 1930s, ‘40s, and ‘50s, Jack Rosen worked as a safety engineer at the Waldorf Astoria Hotel in Manhattan. Throughout his three-decade career with the renowned hotel, he met countless famous figures and began to sketch caricatures of them.
Jack Rosen had many of his pieces autographed by their subjects, creating an unrivaled collection of irreplaceable artwork.
You can find dozens of these incredible caricatures on display at Jack’s Place. Browse our gallery to see likenesses of figures like Queen Elizabeth II, Marlon Brando, Winston Churchill, Barbra Streisand, and Albert Einstein.
Check out our directory of caricatures hanging in Jack’s Place for a sneak preview of who you can see hanging on the walls and where in the restaurant you can find them.
If you’re dining with us on a Friday or Saturday evening between 5:30 p.m. and 9:30 p.m., you can have your very own caricature drawn by our complimentary caricature artist.
What to Order
Jack’s Place is known for its steakhouse fare like prime steaks and freshly caught seafood.
Begin your meal with an appetizer like jumbo lump crabcakes served with a key lime mustard aioli, or a hot bowl of baked onion soup with crispy focaccia and three cheeses.
The salads are made with fresh, thoughtfully chosen ingredients that offer a light start to your evening.
There are entrees for everyone to enjoy, from perfectly seared filet mignon to juicy rack of lamb. There’s even an Impossible filet for vegetarian and vegan guests who want to share in our signature steakhouse experience.
Some of the house specialties include seafood dishes like flavorful grilled swordfish and plump seared sea scallops served with truffle brown butter.
There are also plenty of steakhouse classic sides, including our signature Jack’s au gratin potatoes and an indulgent lobster mac-n-cheese.
Throughout the year, you’ll find rotating seasonal specials and limited holiday menus that showcase local ingredients and our chefs’ innovative approaches to classic steakhouse fare.
Pull Up a Chair at Jack’s Place Lobby Bar
If you’re looking for more relaxed lounge vibes, stop by the Jack’s Place Lobby Bar for specially crafted cocktails and a curated wine list.
Grab a spot at the bar or settle into comfortable lounge seating as you sip on something soothing.
Getting hungry? Order sandwiches, steaks, and other specialty dishes from the Jack’s Place kitchen for a casual and delicious meal in a relaxed bar setting.
’39 Poolside Bar & Grill: Sips, Snacks, and Sunshine
Relaxed Dining with Poolside Vibes
Nothing says “vacation” quite like enjoying a tropical cocktail or delicious burger on an outdoor patio overlooking palm trees and a sprawling swimming pool.
‘39 Poolside Bar & Grill is Rosen Plaza’s popular outdoor dining option, offering a perfect view of the waterfall cascading into the nearby whirlpool spa and the beautiful pool deck.
Open daily from 11 a.m. to 11 p.m., ‘39 Poolside is the perfect spot for a casual lunch or dinner (or any meal or snack in between).
Check out our Happy Hour drink menu every day from 4 p.m. to 7 p.m. for specials that will make your evening lounging poolside even sweeter.
Menu Highlights
Even the busiest travelers need to pause and unwind from time to time.
The ‘39 Poolside menu is the perfect selection of fresh salads, burgers, sandwiches, and other filling and delicious items.
Chips and dip, nachos, and our specialty giant soft pretzel affectionately nicknamed “The Big One” are ideal for enjoying on a warm afternoon with a cold beer or a refreshing mocktail.
The restaurant’s menu is ideal for families, solo travelers, or anyone looking for a breezy outdoor lunch with vacay vibes.
Let’s Do Brunch
On Sundays from 11 a.m. to 3 p.m., ‘39 Poolside hosts a bountiful brunch with a morning-inspired menu.
Enjoy an array of specialty benedicts and brunch favorites like thick-cut sourdough French toast, creamy Lowcountry shrimp and grits, and delicious breakfast tacos.
Brunch is the perfect excuse to pair your food with a delicious cocktail or mocktail. Sunday brunch drink specials include mimosas, bellinis, and bloody Mary’s, but you can also pair your midday meal with any vacation-worthy frozen drink or cocktail from our regular drink menu.
Café Matisse: The Heart of Rosen Plaza’s Breakfast Scene
Bright, Welcoming, and Delicious
Whether you’re traveling for business or pleasure, breakfast will always be the most important meal of the day.
Café Matisse is Rosen Plaza’s cozy and welcoming breakfast buffet that offers everything guests need to fuel up for a day at a convention or exploring Orlando’s theme parks.
Stop by between 6:30 a.m. and 10:30 a.m. for a hearty, wholesome breakfast every day of the week.
From made-to-order omelets to an array of breakfast meats and fresh-off-the-griddle sweet treats, everyone can start their day with something delicious.
Lite Bite Express: Quick Eats Without Compromise
Being in a hurry doesn’t mean you should sacrifice your appetite.
Lite Bite Express offers a selection of grab-and-go goodies like sandwiches, snacks, pizzas, pastries, and beverages.
It’s the perfect pit-stop for late-night cravings, on-the-go meals, and last-minute refueling.
Smoooth Java: Caffeinate and Rejuvenate
Another necessity for a long day? Caffeine.
Located in the lobby of Rosen Plaza, Smoooth Java is a coffee bar that keeps fresh Starbucks coffee brewing all day long.
Pair your drink with a freshly baked pastry for the perfect grab-and-go breakfast.
Perk up with your favorite beverage as early as 6 a.m. every day of the week. When you’re ready for your afternoon pick-me-up, we’ll be waiting for you.
Enjoy Breakfast, Lunch, and Dinner at Our Rosen Plaza Restaurants
Whether you’re visiting Orlando or a local in search of a great meal, we’ll always have a seat waiting for you at one of our restaurants.
Rosen Plaza is home to a variety of dining outlets offering cleverly crafted menus to satisfy any craving.
Come and enjoy a special steak dinner, lunch by the pool, or a cup of your favorite coffee. Whatever you’re in the mood for, Rosen Plaza has a menu you’ll love.
