Incredible. Bartending service.. highly attentive and very skilled mixologists! I especially love that they have Japanese whiskey which I have not found elsewhere and maybe it's because I'm not much of a drinker, but I was so impressed with the quality of cocktails and cocktail choices that vibe with the historic flapper theme. It's a really beautiful place to take a date or have an intimate setting and especially love how chill it is. read more

Prosperous Penny - Cocktail Bars Near Me - Westlake Village, California

The ambiance embodies a refined speakeasy aesthetic--intimate, stylish, and thoughtfully curated. The service was exceptional; our waitress delivered a seamless and attentive experience throughout the evening. The standout recommendation is the Wagyu beef burger--rich, indulgent, and executed to perfection. The drink menu is well-balanced and appropriately priced for the caliber of the establishment. My only critique: the absence of a smoked Old Fashioned, which would have elevated an already impressive cocktail program. read more

We stopped by Prosperous Penny while waiting for our reservation at another restaurant in the hotel, and it turned out to be such a great pre-dinner spot. It's a speakeasy-style bar inside the Four Seasons Westlake Village with a really sophisticated, cozy vibe. Dim lighting, elegant décor, and it feels intimate without being stuffy. The drinks were well done..handcrafted and balanced. I ordered a dirty martini and it hit the spot. For food, we shared the Chips & Caviar, which came with French onion dip, caramelized onions, crème fraîche, topped with caviar (wish there was more of it) and house-made chips. It was rich, salty, and perfect to snack on with cocktails. Overall, it's a great place for drinks if you want something upscale and relaxed. Definitely a nice stop for cocktails before dinner or for a chill night out. read more

Prosperous Penny - Chips and caviar - Cocktail Bars Near Me - Westlake Village, California

This place def is a hidden gem. I didn't realize it was inside the four seasons hotel until we arrived. Once you enter the hotel it's left from the lobby and there is a blue door that is to the bar. From the start, I immediately love the ambience. The dim moody lighting was perfect for a relaxing evening. It's not a large bar but it's intimate and cozy. There are comfortable leather chairs at each table and leather sofas where you can easily pass the time with a cocktail. The drinks were amazing, worth the price. I believe the first drink I ordered was called La D Paris. The service was good as we were provided our own bowl of olives and nuts To have with our drinks. I always appreciate establishments that have someone dedicated to making sure you have water at all times. We never had to ask once. Our server Courtney was great and even ask questions about our tastes upon ordering specific drinks. She was very personable as well. Overall great experience. The only reason why I didn't give it 5 stars was because I noticed we had an additional charge on our credit card separate from what we had a receipt for. However, after a few days that pending charge disappeared. It could have been an accidental charge so I'm giving them the benefit of the doubt, more that it didn't actually go through. I would come back again. read more

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Loved the drinks and layout. Good customer service. We just came from dinner so we didn't get any food. Next time I'd like to try something from their food menu. read more

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In my lifetime.... I have found all types of Pennies. And you better believe, if I find a Penny... I am, 100% picking it up! (Yeah, I'm that guy!!) I have found: -Shiny Pennies -Tarnished Pennies -Lincoln Pennies -Wheat Pennies -Steel Pennies -Pennies that are heads up (a Lucky Penny) -Pennies that are tails down (an "Unlucky" Penny) And for the first time ever..... On April 17th 2025.... I found..... The one, the only, Prosperous Penny!!! ----------------- Here's the backstory... My wife and I wanted, No, We needed a Date night out! So she suggested going to our local wine bar that we are members of and happen to be friends with the owners. Earlier that day, I texted my buddy and said, "hey what's going on at the wine bar tonight, we are thinking about coming through." Sadly, our friends said they weren't going to be there that night and that their cousin was filling in for them... Womp Womp Womp O.k., Now what!? I let my wife know the bad news and I immediately went on my 'ol trusty Yelp App. I scrolled... And scrolled..... And I scrolled some more... And then suddenly ..... There. It. Was. THE PROSPEROUS PENNY After looking at the virtual menu, checking out the pics and reading a few of the reviews.... I knew immediately that the... Crisis about our wine bar had been averted and we were back on track for our Date Night. So I texted my wife and said, "I found us a place, be ready, see you tonight!'" After work, I rushed home, got ready myself, fed the kids, made sure grandma was good and off we went! Side note: Let's just say, my wife was more than excited that I did all the planning for our spontaneous date night and she couldn't wait to see where I was taking her. Located inside the Four Seasons, Westlake Village Hotel, the Prosperous Penny awaited our arrival..... Wait! Why is it so dark in here??? Yes, just my luck! (I never should have picked up that penny that was tail sides up)... Right before we walked into the hotel lobby, there was a power outage at the hotel and the backup generators were in the works of getting switched on. I asked the concierge if the Prosperous Penny was still open despite the lights being off and she said yes, but the kitchen is down so probably wouldn't be able to order any food. So we decided to give it a shot... Hey the battery operated candles they set out are Romantic right, Right? We looked at each other and said, "well we're here, let's make the best of it!" So we sat at the bar and each ordered a drink. A whiskey sour for me... A "Her Majesty" specialty cocktail for the Mrs. And despite the lack of proper lighting... The mood, the vibe, the ambiance was just what we needed. After approximately 20 minutes or so and us talking about finishing our drink and going somewhere else as we wanted dinner and the lights were still off and the kitchen was still closed... Our Luck suddenly changed!! If you believe nothing else today..... BELIEVE THIS! The barkeep came up to us and she saw our glasses were empty and she said, "how about another drink?" (Mind you, we were planning on leaving so we could go elsewhere to get dinner) And just like that...... The lights came on!!!! So I told the barkeep, "well if that's not a sign to get another drink, I don't know what is!" She laughed, I laughed... And we were instantly back in the game! Round 2: A glass of Red Wine for me, another Her Majesty for the wife. As soon as the lights came on, the jazz player started doing her thing and within 30 minutes, the Prosperous Penny was: The. Place. To. Be. For dinner (pub style eats), we split their Crispy Campania Artichoke and Double Smash-cheeseburger with fries and they were both fire! So much so... That the guy next we to us (who didn't look like a cheeseburger kinda guy) asked how the burger was and after sharing our opinion, he opted in for one too. Hey, I'm a trend setter, what can I say? ;) After another glass of red wine for me and an espresso martini for my wife.... We looked at each other and said, best date night ever!!! During our time here, we had such a nice conversation with our bar tender and despite the night starting off in the dark, it turned out to be an evening we will never forget. And let me tell ya... We. Did. Damage. Two Hundred and Fifteen shiny Pennies later.... But you know what? The Prosperous Penny was worth it! It was worth.... Every. Single. Penny. read more

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One of my favorite places to unwind after a long week in the Westlake/Thousand Oaks area! Such a vibe. Amazing food, and cocktails. Ask for Sherry she is an absolute gem read more

Prosperous Penny - Celebrated my "Burlesque" birthday here- it was the perfect ambience for the theme - Cocktail Bars Near Me - Westlake Village, California

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This speakeasy/lounge is located inside a Four Seasons hotel. The decor is super fancy, the servers were fast, and the drinks were delicious. We were able to find a couch to sit on before the Lounge got busy. As the DD, I ordered a very delicious mocktail and a caffeine welcome mocha. Friends described the cocktails as tasty and strong. Each drink ordered had a colorful and beautiful presentation. The bartender service was fast and friendly. He would make drinks, walk around the room and ask if another drink was wanted, and then make and bring them to our couch area. A lady would walk around pouring more water into our glasses. My glass never got more than half empty with water. She was on top of it. Seriously, I was in awe of the service considering the large size of the crowd. Unfortunately, the drinks are expensive, but let's be honest. What isn't nowadays especially considering a lounge inside a Four Seasons hotel. This is perfect for a special event. It was in honor of my husband's birthday, so Happy Birthday husband. See you next year (hopefully sooner) Prosperous Penny! read more

The drinks and live music on Thursdays are excellent, but the best part about this place is the service. Heaven and Edixon are especially kind, acomodating, conversational, and make me want to come back week after week. read more

Prosperous Penny - Cocktail and live music - Cocktail Bars Near Me - Westlake Village, California

I was walking through the Four Seasons on the way to the spa when my eye was caught by the open door of the Prosperous Penny blocked by and elegant rope. A standing sign advised the Prosperous Penny would be open on Friday and Saturday evenings for libations and an assortment of finger foods. My anticipation heightened and I knew I had to make sure to spend some time here later in the trip! We went Friday and Saturday and had great time surrounded by the dark wooden fixtures and elegantly clad chairs. The clientele was upscale and friendly. The service was amazing and they must have all been to charm school (you can tell when someone enjoys their career and it shows). Have them bring some complementary warm nuts to munch on while you're sipping your perfectly prepared cocktail. read more

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IYKYK! This place is such an amazing local gem. I *love* that they have live jazz musicians a few times per week to set the ambiance right. Great swanky spot with artisan drinks. The perfect place to immerse yourself in another world for the evening. read more

Hidden gem in Westlake Village. Don't tell anyone. Perfect atmosphere. Great drinks and great food from the Coin & Candor.

For the last month the Prosperous Penny has been my weekend place to go to for drinks in evening. Janis, Heven and Connor are always very friendly and provide outstanding service. They always acknowledge me when I arrive and I must say the drinks and service are always spot on. My drink of choice is always Jameson Rocks. They are inside the Four Seasons Westlake Village therefore, if you are in the area, check them out. read more

Prosperous Penny - A perfect Friday evening - Cocktail Bars Near Me - Westlake Village, California

They recently added a mixology class called "libations with penny" and I went by myself, with an open mind and had the best time. It's a newer class so it ended up being a nice 1 on 1 with my instructor Janis. I was taught how to make two drinks, their history, and a few other fun facts along the way! I can imagine this would be a fun class to take with a group of people or even on a solo date:) I'm currently sitting outside on the patio with a beautiful view and a wonderful summer breeze. I can't wait to bring my friends here so they can experience the ambiance of the one and only Prosperous Penny! read more

Prosperous Penny - Balcony view - Cocktail Bars Near Me - Westlake Village, California

I went to this bar after a nice dinner. My husband and I ordered a couple of drinks, he got an old fashioned and I got some citrus type of drink. Both were very strong but great! It did take a while for us to get our orders, so I can't comment on the service much. They also mentioned that they could not make an espresso martini because their machine was down, which tends to happen often there. We went around 8:30 pm and by the time we left at 10ish- the place was packed. read more

Prosperous Penny - Cocktail Bars Near Me - Westlake Village, California

Prosperous Penny will forever hold a memorable place in me and my wife's hearts. We celebrated with brilliant cocktails here after our wedding and we couldn't have picked a better place to end our special day. The bartender made us a drink that I only wish I could replicate at home, a twist on the original penicillin I believe. To top it off, an older gentleman bought us a round of drinks for our wedding party. The music, ambience and the drinks were just what we needed after a long year of wedding planning. Make this your last stop when you're in the area. read more

Prosperous Penny - Cocktail Bars Near Me - Westlake Village, California

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Beautiful ambiance with a blue wood paneling bar that has a speak easy feeling. The gold leaf ceiling however tells you, that you are in a very nicely appointed venue. The cocktails were expertly crafted and the generous spacing between the tables ensured you can have a private conversation with your company. Super comfortable chairs will allow you to hang out for as long as the bartender will serve you. See you there! read more

Prosperous Penny - a glass of alcohol and a drink on a table - Cocktail Bars Near Me - Westlake Village, California

I had a blast with Heaven my server! It was a live jazz night!! I'm vegetarian and I got a delicious cheese board. The cocktails were AMAZING! Definitely will be back for their jazz night 100000% read more

Heaven & Janis were awesome! Their service was great and they were knowledgeable on suggestions. I came on a date night and the ambience was romantic, definitely coming back soon! read more

This bar in the Four Seasons is finally reopened. Atmosphere is nice, and they have good drinks. Seemed a bit overpriced, but what we had was still good. Wouldn't make a drive to come here, but I would return if I was in the area. read more

Prosperous Penny - Bacon Old Fashioned - Cocktail Bars Near Me - Westlake Village, California

Prosperous Penny is only open on Friday and Saturday nights in the Four Seasons in Westlake Village. The vibe is chic but dim. There's seating at the bar, but there are a few other couches to sit on. It feels very cozy, mellow but an elevated experience. I have never tried to order food here, and I don't know if they serve any. I've popped in after I've eaten at Coin & Candor for drinks. The drinks are great, as are the bartenders. read more

We popped in last night after being left hungry by the tiny portions at WeVino, and as always, this place hit the spot. The bartenders were super friendly and attentive. We ordered a cheese and charcuterie board curated by our bartender--so good! The sourdough with butter was also excellent. This bar has become one of our favorite spontaneous stops--always a great vibe and consistently delicious bites. read more

Cute little hidden gem! The staff and vibe were remarkable! All of our drinks were carefully crafted, very presentable, and most importantly strong. Worth every penny--will definitely be back! read more

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Awesome small bar! Heaven was an amazing server. Very kind and extremely knowledgeable. Good small bites.

Great ambiance, service and drinks! It was pretty busy the night I went but mostly bc of someone's birthday that brought in a lot of people. Highly recommend for a nice dark, romantic with small sitting areas around. read more

Really cute place. Good drinks and cool vibe. It's a lounge vibe so you can hear your company talk and there was enough room for everyone for a small gathering. Great service! Bartenders were really friendly. read more

The vibe is incredible and the service is unmatched compared to other local establishments. 10/10 would recommend giving it a try!

Ambiance, food, and service are all amazing. Love the decor and vibe, and it's refreshing to see people out in Westlake past 9 pm!

I think this might be a great place to host my 40th. We walked in today and immediately was sold on this location and vibe! read more

Prosperous Penny - Bar Top & tables and chairs. - Cocktail Bars Near Me - Westlake Village, California

12/16/22. Lobby bar vibe. Meh, a bit stuffy, but decent spot. Overpriced drinks. Recommended by my boyfriend's client. Holiday menu was not updated, and 3 of the drinks we ordered were unavailable. Female bartender, short hair, sold us a peppery red somehow skirting around the "increase in price," when I directly inquired. Glass cost $27 per bill at close. Deceptive. Lame, next. Disappointing for such an upscale and beautiful hotel. Will not be back. read more

Prosperous Penny - 12/16/22. Decent spot but silly prices. Dishonest female bartender. Only found out glass was $27 after given the check. - Cocktail Bars Near Me - Westlake Village, California

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If it's possible to up the ante on 'grabbing a drink', Prosperous Penny has succeeded. Whether you are local or visiting from out of town, the personalized service you receive here is what is key. Before the end of your visit, the bartenders will know your choice of libation, know your name and remember more about you than you realized you'd told them! I challenge you: if you are an Old Fashioned person, ask Bob for the Smoked Old Fashioned. Or try the Apple infused Tequila Old Fashioned. Broaden your martini borders: try the Cucumber Martini. Likely the best I've had: so smooth I don't even realize I should have stuck with one! If you are looking for someone to talk shop (alcohol shop), Bob is the conversationalist you hope to find behind the bar at a place like PP. The patrons are just as conversational as the staff, looking to enjoy an evening out and make friends to join them back for another night at PP. Cole and Austin are wonderful servers. I don't think I have ever seen them frown and they are always on their toes. The are also very knowledgeable, don't be shy to ask them for their opinion! George and Sen are also ensuring that both staff and patrons alike are well-taken care of. It's good to see a team working so well together to make the experience of the PP a memorable evening. Thank you Austin, Bob, Cole, Eric, George and Sen! read more

Spent a bit of time in here waiting for a friend and I have to say I was pleasantly surprised. Sort of a speakeasy-style bar with bites to eat as well and plenty of room to sit comfortably. The decor was tasteful and clean and the drinks were phenomenal. Nothing, however, compared to the service I experienced and the conversation shared with Cole, my server. He was friendly from the minute I walked in the door, extremely knowledgeable on the wines available and which would best match my taste, and encouraged my other guest to try a cocktail that he very thoughtfully helped her pick out. She LOVED it. From a normally very picky drinker, she has wanted to return since for that very drink! I would highly recommended the Penny to anyone in or around the 4 Seasons, and will definitely return, myself. Never would I thought I'd say this: but I hope to be waiting on a friend at a hotel for an hour and a half again! Thank you Cole for your knowledge, thoughtfulness, and humor. read more

Great time here at Prosperous Penny. Bob the bartender was amazing. He made us great cocktails and hooked it up with dat popcorn. read more

Prosperous Penny - El Diablo, spicy popcorn, and Dilly Dally. - Cocktail Bars Near Me - Westlake Village, California

Had an amazing time here! Beautiful decor and ambiance, drinks that were creative and oh so tasty, and a cheese board that just made the whole night even better! Amazing and sweet staff! Bob the bartender is a very attentive and talented mixologist that pushes the limit with flavors and presentation! Try the cucumber martini for a cool refreshing drink, cucumber watermelon martini that reminds you to relax because it is summer, and lastly the espresso martini to wrap the evening! Will be coming again. Perfect place for a date night or a fun night with friends! read more

Made it to the Prosperous Penny last night located at the Four Seasons hotel in Westlake Village. The interior is decorated with blue colored walls, low light, and just a couple of flat screens for those who like to glance up at sports scores. The volume level inside is comfortably quiet. They serve beer, wine, and cocktails. Their cocktails are more in the speakeasy style. I enjoyed the Money Penny (and the Bond reference even if it wasn't intentional). The bartenders are creative mixologists in their own rights. I had fun ordering drinks by requesting a specific color. "Surprise me with something red." "How about something blue to match the walls?" The bartenders rose to the challenge by creating great tasting concoctions in the specified colors. I didn't have any complaints about the food either. We enjoyed the bruschetta and skirt steak tacos. Our bartender, Ryan, was even nice enough to hook us up with reservations at the restaurant next door (Coin and Candor) then escorted us over when our table was ready. Nice touch! The Prosperous Penny is worth stopping by for quiet cocktails and easy eating. read more

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Stumbled upon this little gem while staying at the Four Seasons Hotel. Our server, Cole was very attentive and anticipated our needs--he gave a great recommendation when I (vaguely) asked for a sweet drink! We ordered a cheese board and it exceeded our expectations! Great place, great environment and even greater service..highly recommend this place read more

Prosperous Penny - Delicious charcuterie board!! - Cocktail Bars Near Me - Westlake Village, California

Great experience! Friendly, skilled staff. Cannot go wrong with the food and drink selection-everything is tasty! The avocado and pistachio dish is great! The staff is warm, considerate, and want to make sure you have a good time - George, Sen, Bobby, Austin, Cole, Grace! Will be coming back! read more