I have been going to Jack Willes 's for years. The atmosphere is always welcoming and the food is outstanding.

Our server was great, prompt & attentive. But it really felt like everyone working was in a bad mood - probably because everything indicated they were short staffed on a Holiday (Memorial Day) which blows for them. We came here in 2024 and it was really mid-tier. Came back today & while the menu has expanded a little, it's still not great. The ranch dressing on the 'dinner salad' (that is the size of a side salad) was incredibly salty. The burger was half undercooked and the blue-cheese was more 'potent' than normal, husband said it tasted like paint thinner. Beers from the outdoor bar were only slightly cold. Just kind of disappointing. We probably wont be back - 1. Because we're moving further south & 2. It's just don't worth the money or time, go to TBBC down the road, or hit Safety Harbor if you're really itching for a water view. read more

Love the late afternoon weekend vibe with some great live music. A hidden local gem where you find more locals than tourists.

This is a total divey, adorable, tiki bar and grill right on the water. Our entire soccer team and all of their families were coming down here for national and I contacted the establishment few weeks before we were to head down here. Not only did they accommodate us, they set up a special menu just for our party. The food was great and the servers were amazing. Thank you Pete and the Jack Willie's staff!!! read more

Jack Willie's Bar - Look at how the accommodated our group! - Bars Near Me - Oldsmar, Florida

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A very casual, divey place. It's on the water, which is nice, but the live music did make it a little hard to socialize. I didn't see any games except a ring toss, but the way it was positioned, the rope with the ring kept hitting the wall behind the pole, so I don't believe the toss is solvable. There was a sign off to the side that mentioned gator bites, but they didn't have any when we went (was more of a door prop than an advertisement). We did a split appetizer share with garden salads, fried calamari, boom boom shrimp, and fried scallops. While it may have been a mistake on our part to have so much fried food, they were all good and hearty portions and great for sharing. The food was reasonably priced, so if you stay inside or are coming for the music instead, it can be a nice place to meet up with friends. read more

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This is a nice place, good service but my issue is there was a 20% unchange for 8 of us plus a 2% for using my card. Just an FYI is that I or anyone else in the party did not leave an additional tip. You would have made much more money if you'd let us choose what that tip amount should be and the amount would have been very positive for the server and more than the 20% you charged. I know that's probably something everyone wouldn't do but we were a gay gaggle and we are known for great tipping. read more

Top notch all the way around. Music was good (Mike Kremer was on acoustic) the waitress Bella was really great... She Kept checking on us, Super friendly ! Will definitely be back read more

Jack Willie's Bar - Bars Near Me - Oldsmar, Florida

When we have guest in town our first stop is always Jack Willie's. The outdoor seating is fun and alway friendly staff and helpful about menu. The seafood is great here and large portions. The prices are also very good. Really feel like you're in Florida with laid back water front views. I have had many items on the menu and it's always consistent and fresh. read more

The food was good, but everything else was a mess. We ordered Rum buckets that had little to no alcohol. When I mentioned it to our waitress, her response was, "Well, I made it. You'll feel it later," instead of fixing the issue -- which was strange and dismissive. Although they close at 10:30, the lights were turned off on us outside at 9:45. We literally sat in the dark. Service felt rushed, careless, and unprofessional. We paid $40 for two Rum buckets and felt absolutely nothing, even after finishing them within an hour. Good food, bad drinks, worse service. Not worth it. read more

Great and plentiful food. Our Server, Bella, was absolute wonderful and very attentive.

The wait staff is not friendly, and we asked a bar tender for some Togo boxes and he said "that's not my job". It was just extremely rude. Gratuity was added to parties of 6 or more. Which isn't unheard of, just wanted to let you know. The food was just okay, I got the fish tacos, and it was caked in so much coleslaw that the fish was almost nonexistent, the fish was there but it just tasted like coleslaw. The crab fries was okay, the cheese was too melted that it was hard, and some of the table had a sauce drizzled on it and some didn't, so not sure what that was all about. We did get the seafood stuffed mushrooms, and the filling tasted frozen, not fresh. Over all I was just disappointed with the food. I wouldn't go back the next time I am visiting Florida. It was a neat atmosphere, it was a rustic tiki bar feel, we asked to sit inside. There's not a lot of setting inside, way more outside. read more

Jack Willie's Bar - Fish Tacos with crabmeat fries - Bars Near Me - Oldsmar, Florida

Fun tiki bar dive bar. On a quiet water inlet. Cheap beer, ok food, fun ambiance. Shannon our server was spot on. Go for the wings. Excellent. For a tiki bar hush puppies killed it Sorry, to say but today I was picking 1" spines from my Mahi, which was dry. Friends burger was good but a little overcooked But again a fun on the water dive bar. read more

Fun Bar And the band we saw was called tangerine cream they were a great band, fun and played a great selection of good music plus they could play...... Food was good and our waitress Did a great job keeping up with us. Thank you 10/8 /2025 read more

Went with a few friends and they started closing at 730 pm. We were out by 8. My suggestion is to call first. Don't expect too much of staff. read more

I've been to Jack Willies many times with a great experience, but went Thursday, Oct 24, and the dish I always get was terrible. My grilled red fish was so crunchy I had to pick it up and eat it. The hush puppies were delicious as was my sweet potato fries. My friend got the same meal but with spinach. Her fish was also very over cooked and the spinach had so much oil in it, she drained it and had about 1/4 cup oil. This isn't normal for this restaurant so we're caulking it up to a bad cook; but it'll be awhile before we return. Service was ok, but slow, and the young male waiter really didn't know what he was doing. Ambiance is the best vibe so I'm hoping for improvements. read more

Great service , food and drinks in a fun atmosphere. We go several times when we're in the area for a month or so.

Hadn't been for awhile. Food and service was very good. Live music on a Sunday afternoon. We will be back soon! read more

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Jack Willie's is one of our go to's for a good burger or sandwich and cold beverage! It's kind of tucked away, so it's definitely more of a local hangout which is great! They have live music on the weekends and draw a fun crowd! read more

Jack Willie's Bar - Philly beef sandwich - Bars Near Me - Oldsmar, Florida

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Have been here many times, most recently 3 times in the past month alone. It's a fun tiki bar with live music on weekends. It's almost hard to find (behind the barber shop) if you don't know where it is. I always order various seafood menu items, especially the shrimp, mahi or grouper. Stick with them and you won't go wrong. My wife and son have ordered the burger and tell me its great. The shrimp are the absolute best, huge fat, juicy and fresh no matter how you get them prepared. Grilled, jerk, fried, bang bang, buffalo, in a basket, wrap or po-boy. I've had them all. The menu is actually pretty big with a variety of apps, sandwiches, bowls, wraps, entrees.. The service has always been great with a waitress stopping by every few minutes. Your glass is never empty and you won't leave hungry. read more

It has been maybe 15 YEARS since we've eaten at Jack Willie's and I can't understand why. We would eat here all the time and then when it changed hands I think we lost interest... until today. We were with a large group of friends who had seen it driving into the city and asked about trying it for lunch. We did, and I'm sooo glad! They immediately made space for our large party in the back room, and our drinks and food came out so quickly. Our group ordered scallops, soups, salad, kids chicken fingers, a club sandwich, a Philly, a BLT, a couple orders of fried clam strips, and I had the French Dip. EVERYONE was impressed with the quality of the food! Even the French fries were (in the words of my 10 year old grandson) "pretty much perfect" -- thick and crispy with no grease. The au jus for my sandwich was savory and not overly salty, the roll was fresh with a slight toast, and the meat and mushrooms were more than enough. The wait staff were really attentive, and we didn't have to ask for anything as they kept drinks full and kept making sure we were taken care of. We also have a large group of guys that meet for breakfast each month, and at lunch we decided to move breakfast to lunch at JW's from now on! We will be back -- I love that it's yet another great place to eat here in Oldsmar!!! (I can't believe I didn't take pics!!!) read more

Great food and service. Good bunch of people. Uhĥhhhhhhhhj. They want more thoughts before I can post this. I'm old. Have brain fog. Have no more thoughts but I love this place. read more

Service was good, shrimp excellent, if you're a fisherman and know fresh fish, you'll know the grouper and Mahi is frozen. Grouper gets a little funky tasting if it's been frozen for a while. But it wasn't bad. I'd give the fish 3 stars. Great outdoor vibe.. I'd do it again. read more

I had a dinner date at Jack Willie's the other night and wasn't disappointed. I had a glass of Cabernet (I think they told me it was the Josh?, and for dinner I had the blackened shrimp with broccoli and another side I can't recall. The hush puppies were good. My date had the combo platter (the platter where you pick two or three seafood items). He enjoyed his meal. The ambiance is very casual and chill. I felt a touch overdressed but staff welcomed us kindly and let us sit where we wanted. The parking lot (as others have noted) is a little bumpy and could use some repair. I only glanced at the tab but it didn't look like it broke the bank based on our drinks and food order. There was a pretty lively tiki bar outside, but we didn't visit it. Overall JW's is a cool, casual seafood joint tucked away from large crowd dining. read more

Been coming here for years, love the laid back atmosphere, great place for live music and sunset. Awesome tiki bar and a killer menu. Love the hushpuppies, spinach salad is so good, so is the burger, shrimp and gator bites. It gets crowded but in all our years, I can only remember one time the service wasn't top notch- and I honestly think that was a her problem and not a JW or lack of training issue because I never saw her there again. Every time before and since has been great! We've never sat inside- why would you?! LOL read more

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We were on our way to Oldsmar and were feeling like getting a drink so we decided to stop at Jack Willie's Bar. Here's my take on the experience: Quality of drinks: meh. We got the "rum bucket" that was extremely sweet and mostly filled with ice. It tasted like it was made in a hurry and had a healthy dose of the sweetest juice cocktail that one can find. Although the bucket looks big, after I finished it, I felt that I had maybe a rock glass sized drink. Décor: boring. We sat outside and the view was pretty terrible. The water didn't really look clean, smelled bad, and stayed stagnant. There were some metal sticks sticking out of the water in the middle that made the views even worse. Cleanliness: good. The tables and general area was being kept clean. Service: not good. The host/waitress was pretty dry in her responses and did not smile when she seated us down. Price: expensive. They don't have prices listed on any of the drinks and you have you ask individually for the price and all you get are "best guess" or "let me check." Drink and beer prices don't fluctuate like the stock market so just please put it on your menu. It also looked like they don't have a happy hour. I don't know if I'll ever be back here since the drinks were expensive and the views were bad. Most of the time, a place so hidden like this turns out to be a gem but in this case...my experience here was a dud. read more

We had the best service last night from Lizzie! She was so friendly and always checked in on us. We had the redfish that she recommended and the speciality drink was delicious. Looking forward to coming back soon! read more

Super super good! Affordable food that is also delicious (pictured is a plain super burger which comes with fries). I also got garlic bread which was yummy and we sat right by the water! It's shaded but warm :) read more

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Cool dive tiki bar with solid food! Staff was attentive and customers kind. We took our 1&3 yo who loved the acoustic solo show. read more

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Gosh darn it! I really wanted to say nice things about Jack Willie's. But it's not gonna happen. I'll tackle the food first. My Grouper sandwich was $16. It wasn't worth it. I'm used to Grouper being light, flaky and very tasty. This one missed on a 3 counts. It was served with a tomato slice and some lettuce. No cheese, no tarter sauce... nothing. Wife had a chicken sandwich.... Same problem. No condiments served or offered. Our server brought out some tarter sauce after being reminded. Speaking of our server, she was nice, but dealt with our outside table by standing on a nearby deck and, for the most part, conducted business with a railing between she and us. Odd. It's the little things that get me to put a "no go" check in a restaurant's column. Jack Willie's will not see us return. read more

Jack Willie's Bar - Busy deck area. - Bars Near Me - Oldsmar, Florida

I had a great time with some coworkers, but this joint has some warts.... Just to get it out of the way, it's on the water, so of course there are mosquitos. I didn't dock points, that's to be expected. Our server was friendly but the poor guy was not set up for success. When we were there, the inside beer taps were broken, so the only choices were the few beers that were on tap in the outside bar. The beer coming out of those taps could definitely have been colder. They also didn't have a bartender, so our server had to run to the outside bar to fill beer orders, then run to the inside bar to make the cocktails. He also was the one assembling the salads. All in all, he did a good job with an 8-top, but He had to work way harder than he should have to take care of us. The fried appetizers were just okay, though the fried shrimp were large and delicious, probably the best thing I had all night. I had the grilled grouper and a side Caesar salad. The lettuce in the salad was kinda gnarly, several pieces had begun to get slimy. The fish was a bit undercooked and under seasoned. Maybe if the back of house gets straightened out and all, I would give it another try on a future business trip. read more

We absolutely love the prices of their drinks, the atmosphere and the live music! Food is good, if not a little pricey, but still worth the visit! read more

Always the best service and atmosphere at the bar! Beautiful waterfront views and great food for an amazing value! read more

Jack Willie's Bar - Outside boat bar! - Bars Near Me - Oldsmar, Florida

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First time back since May. Food was very different and not the prior quality. We were told they didn't have enough cole slaw for two orders. The fish in the taco's was over cooked and did not resemble Mahi, was some kind of nugget. Server was pleasant! Very few people inside or outside should have been a clue. No entertainment. Came home and researched that it changed hands in July. Doubt I will return, and they probably won't make it. read more

We had dinner at The tiki bar. This is an iconic Florida Tiki bar with inside and outside seating. It was rather chilly tonight so we ate inside. The ser ice was wonderful Lizzie and Laura could not have been nicer or more helpful. Our order came out surprisingly fast. He had an oyster Po boy that he said was one of the best he's had. I was on the fence about a burger or the French dip. I asked Lizzie for her recommendation and settled on the dip. It was very good. We were very pleased with everything. I had an inventive mojito made with coconut rum and it came in a surprise bonus. I got to keep the tiki glass with a mermaid on the front in bas relief. It will make a nice vase in my guest bath that has a mermaid theme. read more

Went there for dinner last night for the second time in 2 weeks. Both times the food was delicious, prices reasonable, and the service was excellent. Great atmosphere too. This will become my go to place. read more

We met some people from out of town there , and I didn't realize how far out it was. But we'll be worth the drive . The shrimp tacos were the beat I have ever had. My husband got the stuffed shrimp, which was good, not great. Service was excellent. I would like to stop again. read more

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Called on Friday, asked if cigars were permitted outside at the tiki bar where cigarette smoking is permitted. The person answering the phone said absolutely. Today is Saturday and was just asked to leave for smoking a cigar. Was told a different manager. Lol. We won't be back! read more

Terrible experience here for a lunch. The place itself is a run down shack on an inlet on the water. You would think it would be nicer being on the water, but it's a dump. Limited seating inside the barely conditioned bar area. There is a slightly larger outside area that's too hot to sit during the day. Our server was high or on something, wasn't completely there and fumbled throughout the service. That wasn't even the worst part, the food! I got the blackened Mahi with fries and broccoli and the fish came out charred and tasted spoiled. Didn't get any of my sides and neither did some of the others that were in our party. We got waters to drink, were asked about regular drinks, ordered them and they never came throughout the entire meal. We didn't bother to ask, just wanted to get out of here as fast as possible. We had a party of 8 so they added their own tip to the bill, otherwise it would have been $0. read more

Showed up this evening with my wife for a few drinks and some munchies. The young blonde hostess told us that we cannot be seated because "the kitchen is backed-up." Seriously? So the whole restaurant is officially closed until your kitchen gets caught-up? How many times a night then do you close and refuse to seat customers because of the kitchen? Was the bar backed-up as well? Never even going to try going there again! read more

Food is excellent, service was first class, and outside seating very pleasant The sweet potato fries are the best