Square Grouper

Small pre-crafted cocktail menu, but every single one of them is amazing. Seriously, not one bad…read moredrink out of the group and for Key West, they are fairly priced. It's a bit small inside, just a few high tops, but they do have some standing room. The vibe and decor are perfect and the musics not so loud that you can't speak to the rest of your party. The men's urinal situation, had me laughing for a long time. My friend and I became much closer

New bar in Key West, imagine that. This place has inside and patio seating. I found inside too…read moredark, I like to be able to see the floor when I'm walking. We only had a drink here, bartender was great.

Bar

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Unicorn heart and I don't know what my husband was drinking

Green Parrot

4.1(487 reviews)

0.6 mi

One of go to spots in KW! Cold beer, good peeps, and live music! Close to Duval and Hemingway area.read more

Always a great time at the Green Parrot. A little off the beat and path and more local than…read moretouristy. Live music great priced drinks and strong pours. Friendly staff. Oh and don't forget the popcorn. Had a fun time there this past Friday night with some friends that live in Key West. If you love good music and a lively atmosphere. This is the place to be.

Rum Runners: On the rocks or blended

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Outside

Tiki House

4.3(141 reviews)

Tiki House - A Must Stop KW Vibe We stumbled into Tiki House…read moreright at opening, lured in by their "street talker" promising 2 for 1 beers and wells from 12-3 PM. Who's walking past that? Not us. Inside, it's pure island charm -- rustic tiki décor, laid back energy, and a munchie menu that's perfect for a quick bite. Football season meant TVs everywhere, plus a solo musician on stage (I don't need to hear the game to watch it; music soothes the beast). Enter Mira -- The Tiki Oracle. Bartender, manager, Key West historian, and all around gem. She switched a TV to our game without hesitation and put up with me talking her ear off like a true bartender therapist. We liked it so much we came back the next day, and the vibe was just as good -- friendly, accommodating, and exactly what you hope for in a KW spot. We even dragged the rest of our group over, and they immediately asked why we didn't start there. Tiki House is so Conch Republic vibed it just makes you feel good. I highly recommend it... even though I hate giving away a place this good.

We had a few birthday celebrations in our group, so we decided to stop into Tiki House for drinks…read moreand a little dancing. The vibe for an early Friday afternoon was really good. The DJ was playing some great music that kept the dance floor going, and the bartender did a solid job keeping up with orders and taking care of everyone quickly. No complaints from our group at all. Everyone had a great time, and we'll definitely be back next time we're in the area.

JungleBird Bowl

Inside

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The Dive Bar Shirt Club

4.0(59 reviews)

0.1 mi

They pride themselves on being a dive bar but this is a good one. Such a great ambiance. Both times…read moreI have been here it's a local vibe feel. People were super friendly and it's just a fun place to hang out. The sign says dogs welcome humans tolerable, lol. I got to see the Hemingway lookalike winner being photographed along with some of the runner ups. The brisket tacos and burrito were delicious and the tacos were served with au jus for dipping. This is 5 star in a dive bar category.

Third time and the food did not a disappoint. Wonderful tacos and atmosphere. Bar tender / server…read more"seemed" nice until she came to pick-up the cups and trays. I said I was going to keep the Aluminum cup as i kept mine from last year. She then changed her attitude and said you are only allowed one per person per day. I handed my wife the 2nd cup which she purchased separately after the meal and the lady stormed off visibly upset. I walked up and told her I did not want to upset her a gave her one of the 2 cups back. Now a 5 star review becomes a 2 star. We will have to see how we feel next year when we come back to Key West. "Post the rule"

A Key West Legend.

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Open daily 11am - 11pm Kitchen 11am - 9pm

The Rum Bar

4.5(445 reviews)

0.8 mi

First trip to KW and our hotel was right across the street from The Rum Bar so we finished up there…read moremost evenings Hands down the best Pina Colada I've had .. No BS .. the best The banana daiquiri was awesome also Lindsey, the bartender is beautiful and very friendly as the others were too Highly recommended

This place is a fun stop with bartenders who know how to make all the great cocktails. This is not…read morea restaurant. Comfortable seating both indoors and out. Great people watching.

The other end of an amazing bar.

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Kenny Chesney Island Girls!! Nothing like these island girls to enjoy with the wife!

Sloppy Joe's Bar

3.9(1.6k reviews)

No visit to Key West is complete with having a cold beer or frozen drink at Sloppy Joe's Bar while…read moreenjoying the piano player slinging tunes or a performer on stage strumming the guitar. Heck, this place has been here since the 1930's and was Ernest Hemingway's favorite hangout. Pictures and memorabilia adorn the walls. A few Sloppy Ritas and Frozen Pain in the Asses and we were feeling no pain. Of course, I had the Original Sloppy Joe sandwich to fill my belly. If you're a fan of historic bars, live music, and a fun atmosphere you'll feel right at home here.

Not the original Sloppy Joe's. No Hemingway stories, other than the transplanted ones. Food is…read moreremarkable average. The signature dish? I make far better. A can of Manwich is far better. Bar is okay. Nothing special. Take pictures of the outside. That's good enough.

Famous cat in Key West.

Original Sloppy Joe sandwich

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Sloppy Rita and Sloppy Ginger

Hog's Breath Saloon

3.6(658 reviews)

0.5 mi

Cool fans at the outside bar and Coldest beer on Front Street. I'd stop here anytime I'm in Key…read moreWest.

First I want to thank all the wonderful employees that helped get my dog cooled down. You guys…read morewere the bomb! They sat us immediately near the fan and brought ice cold water. The water never stopped coming. Even tho I am a Floridian and I know better to walk around during the heat of the day , we decided to go out. Thank you so much again. The local fish dip was wonderful too. lol. Great southern hospitality. Thanks again.

Live music

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Captain Tony's Saloon

3.9(334 reviews)

Captain Tony's is my favorite place in Key West. I'm not kidding when I say I can end up here…read moremultiple times in one day. Every trip, every time. The music is always good, the service is great, and I just love being here. It's the kind of place where you walk in for one drink and suddenly you have been there for two hours. You also have to try to get a quarter in the fish's mouth. DYING TO GO BACK.

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.

Inside

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Better Than Sex

4.5(1.7k reviews)

0.7 mi

I have a sweet tooth, a tremendous sweet tooth indeed, For…read moreice cream and desserts are the things that I need. I've had dessert in the desert near Area 51, And underground in Antarctica, far from the sun. I've had it in graveyards, beneath moonlight so fair, And even in a dessert restaurant, yes, I've had dessert there! At Better Than Sex, the Fever was mine, And it tasted so splendid, so luscious, divine. I tried one of their special coffees as well, And it was so delicious, I nearly swooned under its spell. But the night's grandest moment, the finest display, Was when our waiter arrived with the desserts on a tray. He looked straight in my eyes as he named each delight, With a confidence both curious and wonderfully bright. My dessert was a huge phallus, impressive and grand, With two giant balls resting beneath it in hand. It was covered in "splooge sauce," a curious sweet stream, A dessert of such drama it belonged in a dream! I truly enjoyed this place and would gladly return If I lived nearby, where the sweet candles burn. They are masters of dessert, of flavor and flair-- A deliciously mischievous treasure tucked away there.

We went to Better Than Sex after eating a full meal at Duffy's right in front, so there wasn't much…read moreroom left in us. But oh man was it amazing. An extremely unique ambience and decoration. But it's not too much or too little. The seating is comfortable and private. Our server was very nice, he checked in at all the right times and was sweet. We only ordered one dessert and it got there promptly. Everything on the menu looked excellent and delicious. We settled on the cookie nookie cake, it was super fresh with many contrasting flavors that made every bite a pleasure. Overall had an amazing time and recommend this place for anything from a late night dessert or a full dessert meal. If we're ever around again, we are definitely going back and trying a lot more than just one dessert.

Cream in my coffee

Red velvet cheesecake

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Moscato, white chocolate rimmed glass

Halo Rooftop Lounge

4.4(9 reviews)

We came on a recommendation, and we heard the music from the street below, which made us curious…read more Popped in to have a quick drink, and stayed a bit longer listening to an amazing musician. I really wish I remember his name. Our bartender Maria was super sweet and very friendly! Cool place to relax, have a drink, listen to some great live music, and people watch on Duval Street.

The location is awesome, a balcony above Duval Street, right in the middle of the Key West action…read more If you only want basic beer or wine, *maybe* you'll enjoy yourself. They offer a *very* limited choice of cocktails, and couldn't even make a daiquiri for us. Bizarre. The bartender suggested we go to another bar with a better choice of cocktails, so we did. BTW, they only serve drinks in plastic cups, like a pool bar, if that matters to you. Halo is located in an expensive upscale hotel, but this is definitely not a high end experience.

Dinner menu

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Jeff F.

1 year ago

I recently had the pleasure of dining at the Square Grouper, and I can confidently say it was an outstanding experience! The ambiance is warm and inviting, with beautiful decor that combines modern elegance and comfort, making it the perfect setting for any occasion. The service was exceptional from start to finish. The staff was friendly, attentive, and knowledgeable, always ready to provide recommendations and ensure our needs were met without being intrusive. Now, onto the food--absolutely delicious! Each dish was expertly crafted, bursting with flavor and beautifully presented. From the appetizers to the desserts, everything was a delight to the senses. It's clear that the chefs are passionate about their craft. Overall, I wholeheartedly recommend the Square Grouper to anyone looking for a fantastic dining experience. With its perfect blend of exquisite food, top-notch service, and stunning decor, it truly deserves a five-star rating! I can't wait to return! read more

JD N.

1 year ago

I had an amazing experience at Square Grouper during my recent visit to Key West! Sitting at the bar, I was immediately impressed by the top-notch service from both the bartender and the service bartender. They were incredibly knowledgeable about the menu and made fantastic suggestions that really enhanced our dining experience. The food was outstanding! Everything was super fresh and didn't have that fishy taste you sometimes encounter. I especially loved the street corn appetizer--it was absolutely delicious and definitely a must-try! Even though they were extremely busy, the staff treated us like VIP guests, giving us individual attention and making us feel special. It's clear that they truly care about their customers. I can confidently say that Square Grouper is the best addition to Key West! If you're visiting the island, this spot is an absolute must. I can't wait to go back! read more

Tanja S.

2 years ago

Food is to die for!! Service is great. Will absolutely come back here! Highly recommend!!

Bruce H.

1 year ago

Service was very friendly and the food was great!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

Square Grouper - bars - Updated October 2026

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