Unwind in style at Prosperous Penny, an intimate bar in Westlake Village offering handcrafted drinks, fine wines, and a curated selection of premium spirits. Located within Four Seasons Hotel Westlake Village, this elegant lounge exudes classic charm with a warm, inviting ambiance. Guests can enjoy expertly mixed cocktails, a well-stocked wine bar, and elevated small bites in a sophisticated yet relaxed setting. Whether you're looking for a refined night out or a cozy spot to sip and socialize, Prosperous Penny stands out among the best bars in Westlake Village for a truly memorable experience.
Felt nice to sit in this swanky, dimly-lit, beautiful bar. The live music was great and not too loud to also enjoy conversation. Charcuterie was decent and came with a delicious quince treat.
AA
Alana
Oct 31, 2025
5.0
Tucked away behind a blue door, is a classy speakeasy-themed bar with smashing decor, fabulous drinks, and mixologists with finesse. This clean, sleek gem of a place is my favorite place to have a unique cocktail and bites. The lighting is cozy and on certain nights they have live music. Go, check it out. You can stop by the main restaurant and/or step back in time and enjoy this spiffy and sophisticated spot. Love it.
AC
Alan Ching
Nov 18, 2023
5.0
The food and service is always great. We had a fantastic appetizer sampler and highly recommend it.
MP
Mary Powers
Jul 29, 2023
5.0
Her Majestyπ-- the perfect libation for a "royal lady"!π
Lovely, tasty, and light!πͺ
Thank you, Tate!ππ
PS: Prosperous Penny DEFINITELY needs to be open more days!!π₯πΈπΉ
DS
Deepa Samuel
Aug 5, 2019
5.0
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!
What signature cocktails are available at Prosperous Penny?
Her Majesty, Barrel Aged Vieux Carre, Chi-Tini.
Does this bar in Westlake Village offer a selection of local or international wines?
Yes, Prosperous Penny offers a robust selection of local and international wines.
Are there any small plates or food pairings available?
Yes, Prosperous Penny offers a delightful selection of small plates and food pairings.
Does this cocktail bar in Westlake Village feature live music or entertainment?
Prosperous Penny provides life music through Jazz nights, every Thursday.
Is there outdoor seating or a lounge area for guests?
There is an outdoor seating area.
Do I need a reservation for this Westlake Village bar, or are walk-ins welcome?
Reservations are not required, walk-ins are more than welcomed.
Is there a dress code at Prosperous Penny?
Dressy-casual is the prefered dress code at Prosperous Penny.
Are there any whiskey or spirit tastings available?
At this time, there are no whiskey or spirit tastings available.
Does this Westlake Village bar offer private event hosting?
Yes, Prosperous Penny is available to be booked for private events.
Is there an age restriction for entry into Prosperous Penny?
Yes, guests must be ages 21 or older to enjoy Prosperous Penny.
What signature cocktails can I enjoy at Prosperous Penny?
You can try signature cocktails like Her Majesty, Barrel Aged Vieux Carre, and Chi-Tini at Prosperous Penny.
Does Prosperous Penny offer a selection of local or international wines?
Yes, Prosperous Penny offers a robust selection of both local and international wines.
Are small plates or food pairings available at Prosperous Penny?
Yes, the bar offers a delightful selection of small plates and food pairings to complement your drinks.
Is there live music or entertainment at Prosperous Penny?
Yes, Prosperous Penny features live Jazz music every Tuesday and Thursday from 7:00 PM to 9:00 PM.
Does Prosperous Penny have outdoor seating options?
Yes, there is an outdoor seating area available for guests.
Do I need a reservation to visit Prosperous Penny or are walk-ins welcome?
Reservations are not required; walk-ins are more than welcome at Prosperous Penny.
What is the dress code at Prosperous Penny?
The preferred dress code is dressy-casual.
Are there age restrictions for entering Prosperous Penny?
Yes, guests must be 21 years or older to enter and enjoy Prosperous Penny.
Can you recommend some nearby places to visit before or after your time at Prosperous Penny?
Nearby attractions include the California Jazz & Wine Fest for music lovers, Encinal Canyon for outdoor activities, and the Four Seasons Hotel for accommodations or spa visits.
Is Prosperous Penny conveniently located near transportation or other amenities in Westlake Village?
Yes, it is near amenities like Hertz car rental and various restaurants such as Coin & Candor and The Bar, making it easy to plan your visit and dining options nearby.
Are there wellness and health-related facilities near Prosperous Penny?
Yes, nearby facilities include the Center of Health and Wellbeing and California Health & Longevity Institute, perfect for health and wellness activities before or after your visit.