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    Calypso's Pool Bar & Grille

    3.5 (51 reviews)
    Open 11:00 am - 10:00 pm

    Calypso's Pool Bar & Grille Photos

    Business Info

    CALYPSO'S POOL BAR & GRILLE ATMOSPHERE

    What's the vibe?
    Casual
    Touristy
    Live music
    Good for groups

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    Recommended Reviews - Calypso's Pool Bar & Grille

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    Reviews With Photos

    David R.

    The renovated and wonderful Caribe Royale! This resort does just about everything well enough that you don't have thoughts of wanting to leave for other adventures nearby in Theme Park land. However, on this May Saturday a few thoughts came into my mind that I will share here. First, the pool staff are very helpful and when asked kindly, will help search for a 2 seats for you when none look to exist. Thank you pool staff! Also, they were constantly folding towels on the chairs and making sure all cups and garbage were picked up from guests. Now comes the source of my concern here. There is indeed what appears to be dedicated service from Calypsos to everyone in the pool area on a lounge chair. You could see waiters carrying several drinks at once and dropping them off one by one to the next person almost as if they all asked for something as the staff walked by. However, no such staff showed up to our area which was on the other side of the pool by the bathrooms. It was nearly 100 degrees that day but no worries, I live in this town! We simply walked back across to the Calypso Pool Bar & Grille to find that the to go line was several folks deep and that they would shun you away if you tried to get a beverage from the bar. If I'm a Bar Manager or even the hotel owner, this is a good thing. I would funnel as much staff as I could to help alleviate the seemingly never ending line of people looking for something to quench their bodies. Nevertheless, not wanting to stand in line forever (I did later to get another bottle of Champaign for a friend), we opted to have lunch and sat at a table. The server was prompt and friendly. We went with the hummus which came with pita and carrots/celery, French fries that came with ketchup, and hot wings. This lunch was obviously not a heathy one save for the hummus, but it was about what you would expect from a pool bar at a resort.

    Skillet Mussells
    Karen B.

    Fun outside pool bar, music in the background not too loud. Margarita perfect. We started off with the skillet mussels. I had to remind myself I was at a pool bar. These were so flippin' good! Best mussels I remember having in a long time. Be sure and ask for extra bread to sop up all that goodness. We also enjoyed the Smashburger, the steak sandwich and the Nashville chicken sandwich. They were all good served with piping hot fries. Portions are huge, recommend sharing. Did I mention those mussels! Our server Manny was fantastic, attentive, kept the drink full

    Seating area.
    Steve M.

    We came here to try it out and was a good experience. Manny the waiter was very good. I had the the pichos pichos which is skewers of beef and chicken with green beans and rice. It was very good and they have a nice sweet tea . Wife had the hummus citron which was very good as well. We clear under umbrellas over tables and the restaurant wasn't too crowded. It's on the hotel grounds so have to have a reservation to access this. But prices were reasonable and worth a try.

    Smash Burger and Fries
    Mike S.

    First time staying the the Caribe Royale and Calypso's Pool Bar & Grille is for sure where we spent most of our time when getting a drink or bite. I will say if I could I would give them 3.5 stars but as we know that isn't an option. I will say drinks are pricy and tips in included when you order as well as other resort fees I believe. My go to drink was the Caly Margarita and is mad which the good stuff which I normally don't use but it was for sure tasty. They were $17 each and when I got 2 the total came to $42. For sure I got the Seared Grouper Sandwich for $21 and comes with locally sourced grouper, lettuce, tomato, homemade Tarragon Aioli, on a Hawaiian Roll. This was actually very good and I really enjoyed it. One of the better grouper sandwiches I have had lately. The fish was perfectly cooked and I really liked the flavor of the Tarragon Aioli and the sweetness of the Hawaiian Roll. We also had the Chicken Tenders. These were pretty bad. They were way over cooked and had no flavor. Our food was hit or miss but they and go to the hits. The Smash Burger also looked very good. It's a resort so it's gonna be pricey so just remember that.

    Just learned of these refreshing lil drinks. So good when it's hot out!! We outside!
    Cheryl M.

    The food is very good. Lots of variety from appetizers, shareable items, salads and hearty burgers etc. great pool food. The service is a little slow but it's worth the wait. There's loud music and flat screens everywhere that makes you enjoy the people and your time here! Everything is made to order so be patient. The servers are hospitable and they aim to please. I'll be back tomorrow!!

    Caribbean Jerk Chicken Wrap
    Darren R.

    The Caribbean jerk chicken wrap was ok but it was my bartender that made my experience 5 stars. Her name was Aisha and she was the life of the party! She had people laughing and her service was top notch. She was so authentic just being herself and having fun. I never felt like she didn't love her job and her customers! She brought the energy up in that place. Of all the bartenders I've encountered in my years, her vibe is unmatched!! Aisha made that atmosphere what it was! Fabian was a really cool bartender as well the few times I spoke with him. I loved this place and the staff. I wasn't crazy over the food, although it was good, it just wasn't anything special or unique, but the people behind the bar, that's what kept me coming back. Thank you Aisha and Fabian for making the Super Bowl so fun!! Keep vibing! P.S. I hope ownership does something to recognize these 2 bartenders because they are the reason I kept coming back and spending a lot of money, especially on all the beer and bourbon I drank. You have to invest in your people and recognize them when customers have experiences as great as mine was. Good people are hard to come by when it comes to recruiting employees nowadays, and these 2 are exceptional!! They deserve some sort of recognition and I would love to hear from ownership that they did something for them, or at least, if anything, they should read them my review, so they can feel good about the impact they have on their customers and can understand the level of appreciation that comes with it. Awesome people/bartenders! I can't say enough about how great they made my stay on my business trip!

    Queen J.

    The only thing good about the hotel was this restaurant. Food was good and service was prompt. If you are swimming at the pool I can see why it would be a good go to, since it's right next to the pool. Everything was clean, restaurant had a nice set up and seating was comfortable. All in all it was a great place to dine.

    Virgin Pina Colada & Spicy Pineapple Margarita
    Cindy L.

    We went to Calypso's Bar & Grille for lunch in Orlando. We got Virgin Pina Colada & Spicy Pineapple Margarita. We ordered Poke Bowl & Fish Sandwich. Pretty good.

    Apple S.

    I really enjoyed lunch by the pool in the hotel here but the service was slow and the prices are very high. The frozen drinks were sweet but good. We weren't rushed. The wings were good and the fries too. They were not hot but had flavor.

    two tacos
    Katie H.

    Bartenders are amazing, food is shockingly fresh and delicious. Drinks are strong. Gratuity is included, but they deserve the extra. Must try the tacos or tuna poke bowl , both were amazing

    Steak
    Mahmut E.

    It is an outdoor bar type restaurant with some tables outside and some are inside with no walls. They have selected food, overall it was okay food. Service was little slow because it's also a bar and many trying to get drinks. I actually enjoy sitting there and watching the pool. Price was little high for a bar kind restaurant.

    Addy A.

    I left a review a couple of days ago on Google and I wanted to put one again today. If I want to list the names of the members who are outstanding, I will be here all week! The food was excellent high quality. Shrimp quesadilla was very rich with shrimp and the smash Burger was delicious. Special thanks to Wes, Jonathan, Tami, Manuel Sarah and Fabian. Really awesome people

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    2 months ago

    Paula, Colombia, muy buena mesera, su atencion increíble! Bonito carisma y personalidad

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    5 years ago

    Stale, dry food with bad service--if there were negative stars, I would give them that! Please avoid!

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    Ask the Community - Calypso's Pool Bar & Grille

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    I rarely leave negative reviews, but this experience was so disappointing that I feel compelled to…read moreshare it. From the moment we arrived, we felt unfairly judged. As the hostess walked away from our table, she commented that our group was going to be "nothing but a problem." The basis for that assumption? One member of our party had simply helped clear and organize the table to make the seating process easier and faster for the staff. Yes, we were a lively group. We were on vacation, having a great time at Disney, laughing and enjoying each other's company. What we were not was intoxicated. The situation escalated when one of our friends was accused of being drunk and our entire party of 10 was asked to leave. The problem is that she wasn't intoxicated at all. What makes this especially troubling is that our friend has worked incredibly hard to maintain her sobriety and recently celebrated 12 months alcohol-free through AA. To be publicly accused of being drunk after reaching such a significant milestone was humiliating, heartbreaking, and completely unnecessary. When we brought our concerns to the General Manager, Scott, we expected leadership. We expected someone who would take a moment to assess the situation, listen to both sides, and use his own judgment. Instead, he simply stated that he trusted his employees and made no effort to independently evaluate what had happened. A manager's job isn't to blindly accept accusations. A manager's job is to gather facts, assess the situation, and make informed decisions. In this case, Scott failed to do that. As a result, the restaurant lost a party of 10 customers. More importantly, they deeply hurt someone who has spent the last year fighting for her sobriety. That's the part of this experience we won't forget. Everyone makes mistakes. Great restaurants acknowledge them, learn from them, and treat people with dignity. Unfortunately, this experience was defined by assumptions, poor judgment, and a complete lack of empathy from both the staff and management.

    Photos
    Dining area near one bathroom
    Dining area near one bathroom
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    Cannelloni Al Quattro Formaggi
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    A speakeasy in Kissimmee... I was surprised but I was excited to try it…read more. Definitely different from others I've been too, the entrance was cute & fun to discover our way inside... Interesting space... I see the vision but this is why space planning is so important. Or maybe it's the designer in me. I found the seating very uncomfortable and awkwardly positioned. The services was good and the empanadas were tasty (little greasy) Drinks were yummy... The old fashion was presented in a box while it was being smoked, very cool concept. Overall I dig the concept and I was glad to check it out since I was in the Kissimmee area.

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    Photos
    Bar area
    Bar area
    Pulled Pork Sandwich
    Pulled Pork Sandwich
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    Crispy Bussell Sprouts

    Calypso's Pool Bar & Grille - cocktailbars - Updated June 2026

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