Sleepy Hollow Bar

  4.4 – 316 reviews   • Bar

Sleepy Hollow Bar 32506

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Sleepy Hollow Lounge | Dive Bar Karaoke

5701 West Jackson St. Pensacola, FL, 32506, US,. 850-455-9288. Sleepy Hollow Lounge. Monday: 8 PM Pool Tournament

Sleepy Hollow Lounge in Pensacola, FL, a family-owned bar since …

Sleepy Hollow Lounge in Pensacola, FL. Opened sometime in the 50’s. Still open and I’m third generation in the bar my son is 4th.

Sleepy Hollow Lounge, 5701 W Jackson St, Pensacola, FL 32506, US

Sleepy Hollow Lounge is a lively dive bar located in Pensacola, FL, known for its vibrant karaoke nights and welcoming atmosphere.

Reviews

Devon Peacock
DJ Hei-Hei is a great Dj knows how to keep a good vibe, makes sure everyone is having a good time. Just a good place to go out , do karaoke, have some drinks and hang out.
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Hope Callen-woody
Kj hei hei is awesome i love her to death and she is great at karaoke and great at keeping the crowd entertained and happy i would come out on her days all the time and have a great time
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Zachary Cloud
Gave this place a chance last night 05/02/25 after a friend recommended it to me. I love Karaoke and have checked out a few bars in town. I was told this one does it 6 days a week. At first it was great. Good vibes, bartender was nice and the few people at the bar were cool. It didn’t seem busy which was a plus cause I wanted to sing. It’s what I came for. I waited almost two hours, and nothing. From the looks of the screen there was less then 6 people singing. Only 1 person sang in that whole 2 hours. Why even advertise karaoke at this point?
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Jennifer Newton
Dmitri is a very good friend of mine! He does the karaoke on saturdays. It is definitely a lot of fun to go and hang out. The service there is also great. The bartender works are butt off.
To take good care of you.
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Brian Jacobs
Im a American citizen and got barred for someone else acting out i know the owner would never stand for this. Can’t bar people just because we don’t have the same beliefs. Tammy finds a reason just to kick someone out. . She has a authority problem and im sick of it. I never caused a problem but she made one. Horrible place if she is working. Much love to the owner because they normally set her straight. All the other girls I respect you . Thank you
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Lisa Meyers
This establishment is dirty, terribly laid out, and every piece of “furniture” in this place is mismatched, including the poorly home-made 2×4 scrap piece “bartop” butted right up next to the designated dart lane. I watched someone open the side door of the pool table repeatedly and drop it to the ground so the balls could be accessed like it was broken. Anything ordered to drink other than beer was inconsistent and poorly made. Sound setup was terrible. We went to attend a karaoke contest, could barely hear the vocalists, and then it took them close to 2 hours to tally and announce the winner out of only 20 contestants. When some in our group left and others inquired what was taking so long the owner got confrontational. It was evident they were using the opportunity of the event to generate additonal revenue they otherwise wouldn’t be, so the obvious agenda was to keep people there longer so they’d buy more drinks. West side is already sketch…this place fits right in.
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Brian Swauger
The Sleepy Hallow is a hometown dive bar that has a mix of all people types, colors, and back grounds. When your there your family, and they look loo out for their patrons.
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Kenneth kessenger
Enjoy our visits to the Hollow. Service and prices are great. KJ Hei Hei is amazing.
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Chris Rhoads
Love this place. Owners are great. Bartenders are great. KJ Hei Hei is the best
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Oleander
I love the sleepy hollow. The owner Jennifer is so sweet. The atmosphere is friendly, diverse and welcoming. There is a variety of music and amazing bartenders. Really just a great place to relax and hang out while you forget about the day you had at work.
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