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    Bobby's Monkey Bar

    4.0 (78 reviews)
    InexpensiveDive Bars, Gay Bars
    Open 12:00 pm - 4:00 am (Next day)

    Bobby's Monkey Bar Photos

    BOBBY'S MONKEY BAR ATMOSPHERE

    What's the vibe?
    Divey
    Casual
    Loud
    Happy hour specials

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    Recommended Reviews - Bobby's Monkey Bar

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    Pamela S.

    So this began as an awesome karaoke night . My husband and I were visiting Key West for a long weekend. We stopped in on ga Thursday night to find karaoke DJ Jeff setting up for the evening. Deborah was behind the bar. Both did an excellent job and both were pleasant and easy going. We had such a great time that we decided we were going to come back each night of our stay. We went back on Friday to find Deborah behind the bar and a new DJ named Aramis. He had a big personality but did not run the karaoke rotation well. I went up to ask him a simple question and that resulted in an evening of disappointment. He skipped our turns in the rotation and told us that we should not sing a duet to wasgether and then have a single turn even though the duet was only on one turn. We've been doing karaoke long enough to understand that everyone has different rules. This guy makes them up as he goes along. So we went back to our hotel and decided we would give it another try on Valentine's Day. We go back in time for karaoke to start and find a new x Vicky who is very nice and Aramis again. I was nothing but nice to him I said hello put in our song slips. This time started off well but as the night went on he started favoring his friends favoring people who slipped him money to bump themselves ahead and totally ran a rotation and skipped us entirely. We mentioned something to the bar tender and she said don't argue with him. I wasn't arguing I was trying to ask a question simply because an entire turn had gone by and we were skipped. So first my husband went up to talk to him and was greeted with a very rude response. Then I we cannt to speak with him and he said I don't follow a rotation You're not guaranteed another turn we make our money by getting tips so people that pay us to overhead go first! This was Valentine's Day and there was a huge crowd and I was just so upset that we paid the bill and walked out . We WILL NOT go back because of this rude and very obnoxious DJ. It's really sad that he chose to treat us that way. I suggest that if you choose to visit, you plan to go on a night that DJ Amaris is not hosting!

    Bar area
    Danielle V.

    Stopped here while on vacation in Key West and had a blast. We were there pretty early 9pm, they didn't start karaoke till 9:30 and it didn't get busy till 10:30. We still had fun even though it was dead. They had an old school book to pick a song and it was super dive bar. The bartender was very nice, and we had a great time. It's CASH only but they have an atm on side. Drinks were also cheap!

    Jacob T.

    If you would like to go to a nice little gay dive bar in Key West, then look no further than this place. It is an absolute dive filled with locals and some curious tourist. Every night at 9:30. They have karaoke night again it's a dive bar, but nothing to be afraid of. The bar old, excepts cash and if you didn't bring any they've got an ATM for your convenience. Drinks are strong and cheap. There's no smoking allowed inside the bar so you'll see everyone congregate in the front of the bar where the Astros sit. The staff was relatively friendly. The more you drink, and the later it gets, the better everyone's voices sounded. be sure to have a few drinks before you arrive so you can truly appreciate the karaoke.

    Gin and Tonic
    Sky T.

    A divy bar that is cash only and has nightly karaoke around 9:30-ish. The service is friendly and welcoming. Definitely come as you are and have fun. Really chill and good for a more relaxed night. Outside of that not a bad place to start off before embarking on Duval.

    My partner enjoyed singing is favorite toons. I enjoyed my favorite cocktail.
    Jason S.

    My husband enjoyed singing his favorite tunes. I enjoyed my favorite cocktail. We stayed in Keywest for four nights and made sure we stopped in for a good time. Bartender was awesome and we love the Karaoke host. Can't wait for our next visit in March

    Matt H.

    I never write reviews but this place was so great that I had to drop a quick note. We went here with my wife and her family on Tuesday of this week and had an amazing time! A very friendly bar that seems to have more locals than tourists. We made an effort to talk with the guy running the karaoke night because he was one of the best singers we've ever heard! Go see him soon before he is on Broadway, no joke.

    Matthew S.

    Love this little gay dive bar!!! Typical Key West, very laid back and very chilled. You won't find any pretentious wannabe twinks running around here. Just a solid group of locals singing karaoke with a few out of towners. Everyone is welcome. The bartender was amazing. NO CREDIT CARDS ACCEPTED CASH ONLY SMOKING IS NOW OUTSIDE If you want a chilled place to hang with the locals, have a few stiff drinks and sing a few songs, be sure to stop here.

    J at Bobbys Monkey Bar Key West Fl
    Jj P.

    I have been to this cute little bar many times over the last 8 years. Love the karaoke and the people are soooooo friendly. My next trip to Key West I will be sitting at the bar having a drink.....love the fun and smiles.

    the outside of the restaurant
    Adam C.

    Key West has a chill vibe and the Monkey Bar a great place to find it. Low key may be an understatement but the drinks are stiff and the bartender is nice. It feels like that perfect neighborhood bar where everyone would know your name. My sense was that it was more populated with locals than tourists so it is a chance to meet the real Key West. The only frustration is that they do not take cash. Come on boys this is almost 2021 (because I am so done with 2020) that you cannot expect us to actually carry cash especially in skinny jeans.

    Jeffrey M.

    Just awesome. Go here. Watch old movies. Look at monkeys. Even the monkeys from the wizard. You'll like it. A lot.

    Tess W.

    One of the best bars Key west!! We love this locals joint! Looking for a heavy pour? Look no more

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    7 months ago

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    2 months ago

    Fun place to hang and get some required day drinking in....met some locals and chilled for a while....

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    7 months ago

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    4 years ago

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    1 year ago

    We had a blast doing karaoke here during our trip to the Keys. A fun place with good service and drinks.

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    2 years ago

    Had an absolute blast!! karaoke was on point! Everyone so very friendly! I highly recommend!!

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    3 years ago

    Karaoke bar at its finest! And the bartenders will shock you with their choices of amazing songs to sing all genres. I love this bar!

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    3 years ago

    Looking forward to karaoke tonight at Bobby's monkey bar, right atmosphere great drinks and great service

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    4 years ago

    Fun times and great drink prices! Love having a place that kinda caters to locals. We loved being just "back up" singers!

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    3 years ago

    Great spot for karaoke! Staff was extremely friendly and Dj was awesome! Will come back in the future!

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    Page 1 of 2

    Ask the Community - Bobby's Monkey Bar

    Review Highlights - Bobby's Monkey Bar

    If you would like to go to a nice little gay dive bar in Key West, then look no further than this place.

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    Captain Tony's Saloon - Pirate punch

    Captain Tony's Saloon

    3.9(334 reviews)
    0.6 mi
    $$

    I stopped by Captain Tony's Saloon and it was such a fun, classic Key West experience…read more The vibe is exactly what you'd want, laid-back, a little quirky, and full of character. There was live music playing, pool tables, and even some video games, so there's plenty to keep you and the family entertained while you hang out. Kids are allowed in, but they aren't allowed to sit at the bar. It definitely feels like one of those places where you can lose track of time in the best way. They also have a merch area with hoodies, stickers, and other souvenirs if you want to take a little piece of the experience home. And knowing it's one of the oldest bars in the Keys just adds to the charm and history of the place. The service was quick, you walk up to the bar and order then find a place to sit. Super chill and laid back. One fun thing you have to try is tossing a quarter into the fish's mouth outside... test your luck and see if you can land it! Can't forget the drinks! The rum punch is to die for... super refreshing and perfect for the Key West heat. Overall, such a fun stop if you're in town. Definitely worth checking out! Fun fact: - it used to be a morgue and ice house back in the day. it also used to be the original home of Sloppy Joes, before they moved to Duvall St.

    We were with friends from CO who were visiting Key West for the first time. After walking around…read moreMallory Square and down Duval Street, we decided to have a drink at Captain Tony's before going out to a different restaurant for dinner. Of course it is an attraction because it is supposedly the original Sloppy Joes where Ernest Hemingway hung out. It is dark inside with low ceilings. People have hung paper currency all over and you will also see lots of bras hanging from the ceiling. There is live music and lots of people watching. We enjoyed our drinks and the fun atmosphere.

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    Captain Tony's Saloon
    Captain Tony's Saloon - Inside

    Inside

    Captain Tony's Saloon

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    Bobby's Monkey Bar - divebars - Updated August 2026

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