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    Charley's Pub

    4.2 (5 reviews)
    Open 4:00 pm - 2:00 am (Next day)

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    The Vintage Speakeasy

    The Vintage Speakeasy

    4.0
    (56 reviews)
    7.6 mi
    $$$

    From the outside it does not give "speakeasy" vibes but once inside they did a good job with the…read moredecor and ambiance. Plus you need a password to go in. Looking at the menu I was bit surprised they did not have more signature drinks on the menu, mainly mojitos, but then realized this is a Latin speakeasy, with music playing to match. Once I had my coconut mojito I was very pleased. They really do know how to make them. They also have a full bar so anything you want they can make, The bartender and servers were super nice and friendly, and they worked quick to get all drinks out. They also had some food, that looked delicious, and hope I get the chance to come back to try some. After seating in the lounge/ speakeasy area for a while, we moved to the bar for a last drink. The bartender said Espresso Martinis were her specialty so we order those. She was not lying, one of the best we've had.

    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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    Inside (one angle)
    Inside (one angle)
    The Vintage Speakeasy
    The Vintage Speakeasy

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    Sir Harry's Lounge

    Sir Harry's Lounge

    5.0
    (2 reviews)
    8.7 mi
    $$

    While the lobby bar, Peacock Alley, gets very crowded and noisy, Sir Harry's Lounge is tucked away…read moreand a great place to get a drink in a quiet room. In contrast to the bright and airy lobby, Sir Harry's is dark and surrounded by rich, luxurious, wood furnishing giving it a very clubby feeling. It also helps that the bar is only open on Friday and Saturdays, so it's easy to miss unless you are here on the weekends. As some say that the Manhattan was invented at the original Sir Harry's Lounge at the Waldorf in NYC, I had to try one here, and while they didn't have the greatest selection of rye, they had a few and the price was right (on average $8-$12). Unfortunately, I checked in on a Saturday evening, so I was only able to stop by once, but I would have liked it even better if it were open more than two nights!

    This place is a hidden gem in the Waldorf Astoria Hotel. Very few people know this bar, a copy of…read morethe famous Sir Harry's bar in New York. As soon as you get in, you're in a chic and cozy place with leather seats, wood tables and a very romantic ambience. If you want to impress your date, THIS is the bar you definitely have to go! As for the service, a very nice waiter introduced himself and asked me what I'd like to drink and my name. I was a bit surprised but when I was almost finishing my drink, the waiter came to me and said "Ms Daniela, would you like to have the same drink?". The service is 100% personalized even if there are more than 45 people at the bar! The manager of the bar, Manny Belete was there and checking that the service would be just perfect. I had the chance to talk to him and he is a very nice person with a lot of experience! He has travelled all over the world. I also tried some hors-d'oeuvres and canapes specially prepared by the Waldorf Astoria, complimentary of Eva Cooper, Director of Leisure Sales since I was planning to organize some other events there. I was astonished by the quality and originality of the food. Since it was a long party evening and that I had to drive more than 30 minutes from my house with quite a few drinks, I decided to stay and see how where the rooms. I was lucky to get a special fare for the night and was even upgraded to their Suite! I'll write a comment about the hotel which is definitely one of my favorites here in Orlando. One recommendation for the Harry's Bar: if you want to go, please call before because since it is a hidden place, it is only open when the hotel is almost full or when you make a reservation for a private party.

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    Sir Harry's Lounge
    Sir Harry's Lounge

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    Charley's Pub - bars - Updated July 2026

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