Sang karaoke for my first time here! DJ was amazing and so supportive. Bartender Deborah was great too! You have to pop in and grab a drink and some tunes! When in Key West you got to try something you've never done! read more

A very locals bar, food and service was fantastic. And the ambiance makes you want to keep going back.

LOVE this spot. Walking distance from our house, always fun (karaoke YAY!) but don't tell anyone because then everyone will go and it won't be a dive bar any more LOL JK! Go! read more

Wonderful people Great a karaoke A local bar so don't expect Hollywood but Great crowd Friendly bartender live crowd I love it the first time Will be back if in key west again read more

Bobby's Monkey Bar - Dive Bars Near Me - Key West, Florida

We walked in & almost walked right back out due to the smoke. The place will leave you smelling of cigarettes after just a few minutes. The drinks we're reasonably priced, but we couldn't stay for longer than just one due to the smell and the smoke. read more

Rude bartender! Ask me to pay for every drinks as we go, because they couldn't/wouldn't start a tab (even if I give them my CC AND iD). Dive bar, yet they act like they don't need customers. Bartender would even speak to us. We are locals, and Not coming back. read more

For a bar listing itself as being open and inviting, It was quite the opposite. From the moment I walked in with friends and family, we received dirty looks by staff. After using the bathroom for three minutes there is pounding on the doors hurry up. The DJ who works with karaoke skipped us multiple times and let others go ahead. Also made a scene on stage when one of us didn't put our name on the slip for the song chosen. Stated "I can't fucking help you if you don't put your name in". Just an overall vibe of get out of our establishment. Drinks were mediocre. Unfortunately the taxi driver recommended this place. They will not be recommended by me or receive one more penny from me or anyone I know.. read more

We stop here for a drink every time we go to Key West. Love the neighborhood feel. Met some other friendly locals and had a nice chat. Will return here in the future. read more

This was our third visit to Bobby's and we ALWAYS have an awesome time. It always starts slow, then gets busier and the more people you talk to the better time you have. We are karaoke lovers so when the music gets going it's always a blast. Ever single trip we have met new friends! The bartender each time we have been was Elaine, who always seems super grumpy and even at times rude, but somehow she always grows on me by the end of the night. One drawback, as others have mentioned, is this is a cash only bar. Other than that, it's a great night out! read more

Thinking about it a bit more over the years, this is DEFINITELY the best monkey bar in south Florida

Cheapest and strongest drinks on the island. Shitshow karaoke. Tons of fun. Friendly bartenders. Cash only. read more

Got in late to Key West.. and walked to the closest bar for a drink Walked into Bobby's Monkey bar. Now this is an old school Bar.. Pool Table, Smokey, and pouring strong drinks.. Of course.. Thursday nite was Karaoke night. I'm not a singer but just had to join in the fun.. what was going to be a few drinks turned into a few hours of a bunch of fun with new friends. Hah The locals were great and are straight friendly. This bar is a little bent to the left but... like Homer Simpson said.. I like my Beer Cold and My Homosexuals Flaming.. but it's Key West... read more

One of the things everyone kept telling us before we went to the Keys, especially Key West, was how gay friendly it was. Being a gay couple on our honeymoon this was an extra win for us. I quickly pulled up yelp and searched for places I wanted to go. I chose Bobby's Monkey Bar because it wasn't a big tourist bar. I much prefer the small, more dive bar feeling places to the gay clubs. After wandering around for a bit we were hot and in need of a cold drink. We just happened to be a block away from Bobby's. We went in and got (almost) exactly what we were looking for. It was a small, smoky, and very loved place. It was only the bartender and a usual at the bar. It was perfect for my husband because he is a social creature. He was bursting at the seams to talk to someone. We spent 2 hours in that bar talking to the bartender about Key West and what to do. The bartender explained that while this bar technically could be called a gay bar, over the years it has morphed into more of a locals bar that just happens to have a lot of gay patrons. It was the model of a neighborhood bar. People came and went quickly. Mostly they were just dropping by on a walk to say hi to the bartender or to drop things off for later. Everyone was very welcoming to us too. I think that many people touched on the fact that they got a odd vibe from the locals. I think that odd vibe is the want to preserve their local bar. It is like having a secret surfing spot. Once everyone knows about your spot they all want to come. I think they have a fear that non locals will be rowdy drunk tourists that walk Duval street, or that their little piece of quiet will be disturbed. Show them respect and that you aren't some drunk ass and you will be just fine. Bobby's made our day with a quiet afternoon, good drinks, and excellent conversation. A hidden gem that deserves respect and patronage. 88/100 read more

I'm realizing quickly that hanging out with the locals/semi-locals, you see a whole different (and frankly interesting) side of Key West. This bar is nestled among the residential areas of Key West back in a neighborhood. This was the first stop after flying in that afternoon and it was time for a cocktail. This bar did not disappoint. Small and dark, it was definitely a little dive bar, but in a somewhat charming sort of way. Cash only, but if you show up without, they have an ATM right there. Drinks were cheap and plenty strong. They have a u-shaped bar right inside the door, but if it is full, there is a rail that runs around the place where you can set your drink and talk. They also have a pool table in which several friends took part. If you're looking for a cheap drink with a kick, this is your place. read more

Small bar a few blocks from Duval Street. Cash only, which I'm not thrill about -- and frankly, makes no sense whatsoever given that Key West's economy relies almost entirely on tourism. The bartender was friendly, though. They have a pool table, but you run the risk of whacking people at the bar with the cue. read more

OMG!!! I have been going to key west for years and years and I how come I haven't been to this gem of a place!?!?! There's only a few gay bars in Key West and my husband and I stumbled upon this place on a Sunday night for karaoke after a long day deep sea fishing (dolphin was on the menu). Anyway, Bobby's Monkey Bar has, by far, the cheapest drinks on the island, the sweetest and most lovely bar-maid (don't forget to tip her good!), the strongest drinks, jovial and fun locals, and ice cold air conditioning!!!! Pool table is available for a dollar in quarters and is cash-only. I have no idea why people on yelp complain that its cash only.....at least you know how much your spending on drinks and not blindly swiping your card! But will most definitely ditch the other bars (gay or other-wise) and come back to this place because I think I have found my dive. read more

This bar is the best jump bar key west has.. Its from the busy,craziness on Duval .. the karaoke was fun the beverages are moderate and there's a pool table .. certainly suggest this jump bar it's one of only a handful barely any great spots key west has read more

Was excited to find a local bar to grab drinks and have some fun. Walked in and bought one round of drinks, put the change on the bar, sat at the bar, went to sip my first drink, and bartender came over, pushed our change back to us and said that if we were only going to leave the change, that we could leave. I've been a bartender for 25 years and never treated customers that rude. Had the bartender been reasonable considering we didn't even sip our first drink, we would have stayed and bought more drinks at this establishment. Needless to say, we left a good tip and didn't even finish our drinks, but won't be back. read more

Love a good dive bar!!!!!!!!!! Fantastic place, great happy hour. If you want to avoid tourist traps and drink in a more local joint, come here. read more

Best off duval gay dive bar ever. We always make sure to have a drink, or ten, every time we are on the island. A key west classic!!!

I am sorry to say this but according to this wanna be bartender you wouldnt give a fuck anyways. His words!! I hope this is not true as the owner of this business. I love kareoke and was getting used to place. I will find an alternative and if not i will find my own and wouldnt hire such unworthy candidates. Please note that everone esle has been a peach only that unhumble a hole.. good luck with ur business. U could use it and shity emplyees dont help. I am sorry for being so aggravated but thought u should know the truth... lmk if u wanna discuss..plz and thk u... read more

This is an excellent local watering hole. The only reason they didn't get a 5 star was they are a cash only bar. Convenience is key. I loved the atmosphere and the value. It's on the small side, but that's part of the charm. The locals' banter with the bartender wad hilarious. I'd definitely be a regular if I lived here. Thank you for making me feel like a regular. read more

We read another review that described this as the "Gay Cheers," and it did not disappoint. Great place to chill out and plan your next move, after a day of beach and roaming the city. We got a handful of useful tips from the locals, several of which we tried out later - they were spot-on. Folks here were awesome. read more

I absolutely love this bar. As soon as you enter, you get a wonderfully welcoming. Normal, everyday people who just want to hang out. Some nights, karaoke and reasonably priced beer and cocktails. Highly recommended !! read more

We went here a few times throughout my vacation. Great local place and very friendly staff. They only accept cash, but they do have an ATM. Also Wii bowling is always on and it's likely, you'll see a dog or two with their owners. Very fun place overall! read more

This place could be a lot if fun, but there's limited seating. Unless you're sitting at the bar, you have limited interaction with others. Our bartender wasn't particularly friendly or outgoing, either. read more

I wish this bar were here in Austin; so much fun! Very local, no loud music or naked dancers, simply a bar full of friendly locals lorded over by the very funny, salty, and charming bartender Eileen (I think her name was..) read more

This place was so much fun! As a straight person, you definitely need to be thick-skinned to some uncomfortable glares, but for the most part, the staff and crowd were friendly and accommodating to us "out of towners." Expect a low-lit, dive bar atmosphere with a very attentive bartender and a phone book thick book of every karaoke tune. Guaranteed fun time! read more

Our B&B manager told us this was the "locals" watering hole. Down the street and we walked by, sat on a bench across the street and decided that we were probably to touristy to go in. read more

This is a great place to visit. Only the locals seem to know about it. Great karaoke. Cash only. Eileen, our bartender, was a riot.

Non welcoming cash only bar! Crossed this off the list! Came here over 13 years ago and had fun in this dive bar. Obviously. The bartender was more interested in the locals vs being inclusive. A local said this was a racist bar. But I didn't pick up that vibe. If you travel in a group and like karaoke, this might work read more

We had a good time at Bobby's Monkey Bar. They had karaoke, and if no one was singing then the guy in charge of it would sing. The bartender was nice, but out of our group of 6 I was the only one who didn't order a drink so I didn't get the chance to talk to her. Definitely a fun place to visit at 3am! read more

We had a great time we did Karoake and had a blast time my favorite things was Matateaus hottest bartender ever!! I am coming back for Tropical Heat!!! I loved also the puppy dogs I t felt like a real neighborhood bar can't wait to come back in August!! read more

We loved this place. Not touristy at all and you couldn't ask for a nicer crowd of locals! My bf and I went twice and had a great time. If you're looking for a nice low key place for a drink this is the place to go. read more

Loved this place! Bartenders are very friendly and it had a great atmosphere with cheap drinks. came with my boyfriend and played pool for hours. We'll definitely be going back read more

Definitely a place the locals congregate at, but tourists are welcomed with open arms. Bartender is awesome and fast. We went on a Tuesday night, and they were doing karaoke. (Not sure if it's only on certain days or if it's a nightly thing.) Karaoke host was great. Everyone in there was really cool, crowd was a lot of fun. Cash only, but there is an ATM on site. read more

Great fun place. Rusty behind the bar is a HOOT!!!!! Locals are friendly regardless of your orientation or the time of day. Always sopt by for a drink whenever we are in town. read more