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About the Property

Havana Cabana is a Cuban inspired waterfront hotel in Old Town Key West. The pool is where everything happens. Our food and beverage program leans on great cocktails, Cuban and Latin cuisines and the kind of laid back energy that fits the island. The property is operated by EOS Hospitality, a national hotel management company with a portfolio of independent and lifestyle hotels.

What You Will Be Doing

You will spend most of your shifts behind the bar at Mojitos, our pool bar. It is busy, it is social, and it sets the tone for a guest’s entire stay. When the schedule needs it, you will also pick up shifts at Flama Cabana, our Cuban-inspired cigar bar, and potentially with banquets and private events on property.

We need someone who can move fast without losing the warmth. You know your way around a mojito and a daiquiri. You can keep the bar clean and stocked while still making every guest feel like the most important person at the pool. If you have worked a high volume hotel or resort bar before, this will feel familiar.

Day to Day Responsibilities

Guests

Greet guests as they walk up to the bar. Make them feel welcome. Read the room and adjust your energy to match.

Talk to people. Recommend a cocktail you actually like. Point them toward something good from the Floridita Food Truck. If they ask where to eat in town, give them a real answer.

Pay attention to your guests. Refill water, pace drinks, check in. Know when someone wants conversation and when they want to be left alone.

Handle complaints calmly. Pull in a manager when that is the right call.

Get to know the regulars. Remember what they drink.

Behind the Bar

Build every drink to recipe. Same ingredients, same pour, same garnish, every time.

Know the menu cold. Beer, wine, spirits, zero proof. Be able to answer any question without stalling.

Use measuring tools including a jigger, cups or spoons to always hit the spec. Pour cost matters.

Suggest the premium pour when it actually fits the guest. Do not push it when it does not.

Get your batches, juices, syrups, and garnishes prepped during opening and any slow stretches. You will not have time once it gets busy.

When the menu changes seasonally, learn the new drinks fast and tell the F&B leadership team what is working and what is not.

Responsible Service and Compliance

Card anyone who looks under 35. Do not guess. Check the ID.

Cut off guests who have had too much. Tell a manager. Hold the line on the call.

Keep your Florida Responsible Vendor certification (or TIPS / ServSafe Alcohol equivalent), as well as food service handler certification current the whole time you work here. If you do not have it at hire, you have 30 days to get it.

Follow every applicable federal, state, and local alcohol service law, plus all Havana Cabana and EOS Hospitality policies.

Cash, POS, and Accuracy

Open and close every check accurately. Apply comps, discounts, and room charges only with manager approval.

Process cash, cards, mobile wallets, and room charges cleanly.

Reconcile your drawer and declare tips at the end of every shift.

Tell the manager on duty about any voids, comps, or check adjustments before you leave.

Cleanliness and Stocking

Keep the bar clean and organized at all times. Bar top, wells, speed rails, glassware, garnish station, back bar. All of it.

Follow Florida health code and ServSafe standards on sanitation and hand hygiene.

Do your opening, mid shift, and closing side work. Do not leave it for the next bartender.

Check pars and tell the bar manager what is getting low before you actually run out.

Label, date, and rotate every perishable. FIFO, no exceptions.

Keep the pool deck looking right. Bar, signage, menus, furniture, music, ambient setup.

Flama Cabana and Banquets

Cover scheduled shifts at Flama Cabana, both service bar and guest facing.

Work banquet bars and private events on property. Set up the portable bar, run it, break it down, clean up.

Match your style to the outlet. Mojitos is high energy and casual. Flama Cabana is a little more refined and conversational. Banquets are structured, and you stay out of the way of the event.

Read the BEO before every event. Know your consumption limits, host bar versus cash bar, and guest count before you start pouring.

Teamwork

Communicate with servers, food runners, the kitchen, hosts, security, and managers. Be clear and respectful.

Show up to pre shift. Pay attention during training. Get on board with new menus and property initiatives.

Help out other bartenders and barbacks when it gets slammed. Jump on a different station when you are needed there.

Report safety problems, broken equipment, and guest incidents to the manager on duty right away.

What You Need to Have

At least 1 to 2 years bartending in a high volume restaurant, hotel, resort, or bar.

Solid working knowledge of classic cocktails, beer, wine basics, and standard bar terminology.

Comfortable on a POS system (Toast).

Florida Responsible Vendor Training (or TIPS / ServSafe Alcohol) and Food Handler Certification at hire or within 30 days of starting.

At least 18 years old, per Florida law for on-premise alcohol service.

Strong guest service instincts. You can stay friendly and efficient when the bar is three deep.

Ability to read, write, and communicate in English.

Open availability across days, evenings, weekends, and holidays.

Nice to Have

Prior hotel, resort, pool bar, or tropical destination experience.

Familiarity with Cuban and Caribbean cocktails and the rum category.

Conversational or fluent Spanish.

Banquet, wedding, or private event experience.

Craft cocktail skills (fresh juicing, syrups, infusions, batching, garnish work).

You already know Key West and can give guests real local recommendations.

Physical and Working Conditions

Standing, walking, and moving for 8 to 10 hour shifts.

Bending, reaching, twisting, and lifting overhead throughout the shift.

Lifting, pushing, and carrying up to 50 lbs regularly (cases of liquor, kegs, ice bins, equipment).

Manual dexterity for shaking, stirring, pouring, garnishing, and operating a POS.

Comfortable working outside. Mojitos is open air, so expect sun, heat, humidity, and the occasional rain.

Comfortable in a loud, fast paced environment with constant guest interaction.

Good vision and hearing to read tickets, measure pours, check IDs, and recognize when a guest has had too much.

Schedule

This is a full time role, 4 to 5 shifts per week. Most of those will be at Mojitos, with rotating coverage at Flama Cabana and on banquet and event bars based on what the property needs. You have to be available on weekends, evenings, and holidays. The hotel runs 365 days a year, and our busy stretches land on weekends and during high season.

Compensation and Benefits

Competitive tipped hourly wage plus tips (cash and credit, pooled where applicable per property policy).

Medical, dental, and vision options for eligible full time team members.

401(k) with company match, per plan eligibility.

Paid time off and paid holidays per EOS Hospitality policy.

Employee Assistance Program.

Travel discounts across the EOS Hospitality portfolio.

Shift meal and non alcoholic drinks on the house when you are working.

Uniform top provided. Ongoing training and the chance to grow within the property and across EOS Hospitality.

Equal Opportunity Employer

Havana Cabana Hotel and EOS Hospitality are Equal Opportunity Employers. We hire without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by federal, state, or local law. Our team should reflect the community of Key West and the guests we serve.

To apply, please submit your application and resume through the EOS Hospitality careers portal

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

Havana Cabana Resort at Key West

Experience Cuban Culture In The Heart Of Key West

The Havana Cabana Resort is a destination steeped with charm and character. From classic cars out front, to mojitos and great music poolside, the nostalgic influences from the art and culture of our neighbors in Cuba makes Havana Cabana a lush escape from reality.

Address	3420 N Roosevelt Blvd, Key West, FL 33040
Property Type	Resort
# Jobs	2

About EOS Hospitality

EOS Hospitality is the hospitality division of EOS Investors, a fully integrated investment firm dedicated to identifying and creating value within the hospitality sector. Our portfolio includes hotels and resorts in Maine, Delaware, Washington, D.C., South Carolina, Florida and California.

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BUILD A CAREER AS EXCEPTIONAL AS YOU

Join a community of more than 4,000 ambitious, thoughtful hospitality professionals delivering exceptional guest experiences across the U.S. At EOS, we encourage creativity, ownership, and problem-solving at all levels of the organization, and we are committed to weaving diversity, equity, and inclusion into every aspect of our business.