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Bobby's Monkey Bar

4.0 (76 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
Good for groups

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Recommended Reviews - Bobby's Monkey Bar

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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.

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.

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.

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

Marissa N.

Local or semi-permanent local bar. Smoking allowed inside, kareoke allowed inside, pool, drinking, fun and laugh all allowed. The folks were very welcoming, chatty, friendly and full of applause when people sang.

Entrance

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11 months 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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6 years ago

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7 years ago

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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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4 years ago

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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

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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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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

(332 reviews)

$$

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.

Green Parrot

Green Parrot

(484 reviews)

$$

While roaming around Old Town we stopped in here on a recommendation from a local. He said it's his…read morefavorite spot on the island. It's a dive bar through and through but I happen to be a big fan of dive bars! However, this one fell flat on it's face with the service. I wouldn't say the place was packed but there were not any open seats at the bar. I posted up the best I could but for the better part of 15 minutes both bartenders didn't even come to my side of the bar. I then moved to the other side and waited another 10 minutes to be served (at which point the bartender said "Didn't I just serve you?" Um, no, you most definitely did not. This place has two saving graces: 1) A water jug full of cold water for the taking, off in the corner. Love that. 2) A popcorn machine that had DELICIOUS popcorn! YES. If you can manage to get a beverage then I think you won't mind Green Parrot's (very) relaxed atmosphere and delightful little perks. My takeaway is for the staff to mix in some work to go along with their chatting with the regulars...

I found this to be a great classic place to hang out. Good live music, a lively crowd with a mix of…read morelocals and tourists. They have a great beer selection (including Lagunitas IPA from California, WTF?), good service...what's not to like? The location is a reasonable walk from the cruise ships too. Plus, there are pool tables and a dart board and free popcorn. This will be a definite stop the next time I'm down there.

The Dive Bar Shirt Club - Girls night out overtaking the Dive Bar Shirt Club.

The Dive Bar Shirt Club

(55 reviews)

A night at Shirt Club is less about going out for drinks and more about embracing whatever strange,…read moremagical chaos the island decides to throw your way. This is a true dive bar in the best sense--dark, loud, unapologetically weird, and absolutely unforgettable. The drinks flow, the stories blur, and at some point you realize you're no longer entirely sure how you ended up where you are... but you're fine with it. Now. The ladies' room. If you know, you know. Let's just say there was a handsome fellow, a conch shell, and an air of mystery that felt very on-brand for Key West. Details are intentionally vague--some things are better left unexplained--but whatever was happening worked. Worked very well. My nieces? They fell for it hook, line, and sinker. Completely enchanted. Equal parts confused and delighted. A core memory was made, whether they asked for it or not. Shirt Club is the kind of place where stories are born, logic is optional, and you leave with inside jokes you can't fully explain to anyone who wasn't there. It's chaotic, hilarious, and 100% Key West. Would we go back? Absolutely. Would we ever expect to understand everything that happens there? Not a chance -- and that's exactly the point.

As someone visiting from up north, this place instantly felt like one of those spots you wish you…read morehad back home. The Dive Bar Shirt Club has the kind of laid-back, no-frills vibe that feels like hanging out in your best friend's backyard--the one who somehow has all the toys, great music, and everyone ends up there without planning it. The ambience is pure Florida Keys: relaxed, fun, and welcoming, like you're part of the crew the second you walk in. Then there are the tacos... easily some of the best tacos in the Keys. Fresh, flavorful, and exactly what you want with a cold drink in hand. On top of that, the prices are more than fair, and the selection--drinks, merch, food, all of it--is absolutely top tier. It's the kind of place that makes you understand why people never leave the Keys... and why visitors like me keep coming back. Here's my breakdown Food 5/5 Location 5/5 Price 5/5 The foodie ninja shall return

Bobby's Monkey Bar - divebars - Updated May 2026

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