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Island Wing Company - Rolling Oaks, your go-to Bar & Grill and American Restaurant in Kissimmee, FL! Located at 3267 Rolling Oaks Blvd, 34747, we're dedicated to serving up mouth-watering dishes and a fun atmosphere that'll make you feel like you're on island time. At Island Wing Company - Rolling Oaks, our menu features a wide variety of American classics, including our signature wings, burgers, sandwiches, and salads. Whether you're in the mood for something spicy or savory, we've got you covered. Pair your meal with a cold beer or cocktail from our fully-stocked bar, and you're in for a treat! Our restaurant is the perfect spot to catch up with friends, watch the big game, or simply enjoy a night out with the family. Our friendly staff and casual atmosphere make us a local favorite, and we can't wait to welcome you to the Island Wing Company - Rolling Oaks family!

Island Wing Company - Rolling Oaks Review Summary

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4.2
(770 Reviews)
5
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1
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Destinee Bunn
Destinee Bunn -Google user
a year ago
This was my families first stop after getting off of the Auto Train in Florida. There was 13 of us and we were seated immediately. We had several children with us ranging from 7 months to 15. The drinks were delicious we got the fishbowls...Read More
Dine inLunch$10–20Atmosphere: 5Baked WingsThere are a few games jenga, cornhole, pool, and fooseball. Also the live DJ takes requests for kid songs as well!
Regina Howard
Regina Howard -Google user
6 months ago
Wings and the big boss burger I selected was absolutely delicious. The cocktails was half off and they were delicious
Dine inDinner$20–30Atmosphere: 5Big Boss Burger, French Fries, Garlic Parmesan Wings
Jessica Agront
Jessica Agront -Google user
2 years ago
This is our new favorite wing place. We had the sweet Hawaiian BBQ wings and I had the Honey Stung BBQ.and we took home to my kids the teriyaki and Korean BBQ wings. They were delicious AND The fries were the perfect saltiness and crispness....Read More
Take outDinner$20–30
Yossel Rodriguez
Yossel Rodriguez -Google user
a year ago
Lovely family restaurant to visit and dine in. Caribbean food style with lots of good choices. Good server today, hope it stays like this for a while.
Dine inDinner$10–20Atmosphere: 5
Stephen Marquez
Stephen Marquez -Google user
3 years ago
A friend of ours was in town and invited us out to dinner with some of their family. They chose this place and I was mostly unfamiliar with it. I had driven by as I've been to most every place around it at this point....Read More
C Fish
C Fish -Google user
3 years ago
The place is immaculate! It has just opened and is worth a try. We just had drinks this time but the menu looked great. There is indoor and outdoor seating. There are fire pits outside and lots of seating inside and a large bar. Prices...Read More
Casey Saiz
Casey Saiz -Google user
a year ago
The drink specials are great! The service is great. Every once in a while, the food can miss. Overall, fantastic atmosphere.
Nancee Manula
Nancee Manula -Google user
3 years ago
I am so glad Island Wing has moved to this side of town. Normally when we visit the other location we stick to the norm of salad and wings but tonight we went big. Our server Sanchez was patient with my indecision and went with...Read More
Mark Sullivan
Mark Sullivan -Google user
Edited 2 years ago
I chose this place due to its look and outdoor seating. Sent me vibe and the vibe checked out. Outdoor seating was perfect, very comfortable. The food was a homerun. No fried foods - baked everything from fries to wings. Fried pickles, …
Sean Milliner
Sean Milliner -Google user
3 years ago
I am the grill cook in restaurant. The menu is amazing and atmosphere environment is comfortable and family oriented. Come down check out Over 60 TV's Burgers , Tacos , Flatbreads , Salads , Apps and More !!!
David Baalbergen
David Baalbergen -Google user
a year ago
Cora was a great server! Super friendly and willing to go back and forth the with the kitchen to ensure an allergy was avoided! Coconut shrimp was a little over done, but still tasted good. Would highly recommended the Caribbean Shrimp. Also, it was dead Monday night. Apparently...Read More
Dine inDinner$30–50Atmosphere: 5Caribbean ShrimpOptions for dairy free individuals.
Charles Moore
Charles Moore -Google user
3 years ago
Good food, good service, clean, and tables are generously spaced. The menu has a nice selection. Healthier casual dining with traditionally fried items baked. Good daily specials with generous happy hour. Our server Hilary was friendly and attentive. They have a fun SoS card to...Read More
Maria Rose
Maria Rose -Google user
3 years ago
Stopped in here for the first time today and really enjoyed it. It had a great vibe, delicious food and awesome service. I was greeted the second I came in, and then by my waiter Isaiah and his trainee. They were helpful and patient with...Read More
Patrick K
Patrick K -Google user
3 years ago
The food was amazing. The drinks were strong. Everything was reasonably priced came out to around 30 a person with tip including 2 drinks. Our server Noah did an amazing job.
Tracy Shulick
Tracy Shulick -Google user
2 years ago
We happened to stumble across this place by accident and so glad we did! The staff on duty that day was top notch and the food was yum! Drinks were on point! If you get a chance stop on in. You won’t be disappointed. Jamie...Read More
Dine inDinner$20–30
Alan Aronson
Alan Aronson -Google user
5 months ago
4-14-25 I enjoy coming here. The atmosphere is great, and the food is wonderful. Today I had the 10 baked wings, which were gigantic, and flavorful. And my server Jenni was very quick to return with drink refills and check on us often. If you are...Read More
Atmosphere: 5
Amber Shults
Amber Shults -Google user
3 years ago
Love, love, love this place! The food is great and the service is top notch. They also have several specials throughout the week. Great menu options to ensure you can try something new on each visit. PS - the Baja Fish tacos were esp delicious!...Read More
Ian Davis
Ian Davis -Google user
2 years ago
Service was great, friendly servers and attentive! First time in the chain and will return! Good specials and love to see they support local breweries. …
Leigh Vaticano
Leigh Vaticano -Google user
a year ago
Great place. Service, waitress, gm and food all fabulous. Would highly recommend if in the area. Will return next time in Florida. Had buffalo mac and cheese give it a 10 outta 10.
Wendy Rivera
Wendy Rivera -Google user
6 months ago
Dine-in for the first time today. Husband and I were greeted immediately by Hallee, although she was multi-tasking; she was sure to acknowledge us and take our order in a timely manner. I must say she did a great job!!! Food was great as well....Read More
Dine inAtmosphere: 5

Features

Service options

check icon Outdoor seating
check icon Delivery
check icon Takeout
check icon Dine-in

Highlights

check icon Fast service
check icon Live performances
check icon Sports

Popular for

check icon Lunch
check icon Dinner
check icon Solo dining

Accessibility

check icon Wheelchair accessible entrance
check icon Wheelchair accessible parking lot
check icon Wheelchair accessible restroom
check icon Wheelchair accessible seating

Offerings

check icon Alcohol
check icon Beer
check icon Cocktails
check icon Coffee
check icon Comfort food
check icon Food
check icon Food at bar
check icon Happy hour drinks
check icon Happy hour food
check icon Hard liquor
check icon Late-night food
check icon Quick bite
check icon Small plates
check icon Wine

Dining options

check icon Brunch
check icon Lunch
check icon Dinner
check icon Catering
check icon Dessert
check icon Seating

Amenities

check icon Bar onsite
check icon Restroom

Atmosphere

check icon Casual
check icon Trendy

Crowd

check icon Groups
check icon Tourists

Planning

check icon Accepts reservations

Payments

check icon Credit cards

Children

check icon Good for kids
check icon High chairs
check icon Kids' menu

Parking

check icon Free parking lot
check icon Free street parking
check icon Parking

Pets

check icon Dogs allowed outside