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Pool Server Jobs in Maryland (NOW HIRING)

Benchmark

Room Service Server

Saint Michaels, MD · On-site

$13 - $16.75/hr

Adding to the charm of the resort is a zero-edge swimming pool, lush gardens maintained by our on ... We are looking for a highly motivated, customer focused Room Service Server to join our team! Room ...

Benchmark

Room Service Server

Saint Michaels, MD · On-site

$13 - $16.75/hr

Adding to the charm of the resort is a zero-edge swimming pool, lush gardens maintained by our on ... We are looking for a highly motivated, customer focused Room Service Server to join our team! Room ...

Silver Diner Development, LLC

To-Go

Bethesda, MD

$15/hr

... our servers. They are also in charge of organizing the orders for online order and delivery services like Doordash and Uber Eats. * Make over $15 per hour. *Based on hourly wage+tips+tip pool ...

Silver Diner Development, LLC

To-Go

Bethesda, MD · On-site

$15 - $25/hr

... our servers. They are also in charge of organizing the orders for online order and delivery services like Doordash and Uber Eats. * Make over $15 per hour. *Based on hourly wage+tips+tip pool ...

HRI Hospitality

234 rooms | 16,000 sq. ft. meeting/event space Amenities: contemporary rooms, rooftop pool, five ... This role manages seating, waitlists, guest flow, and communication with servers to ensure an ...

HRI Hospitality

234 rooms | 16,000 sq. ft. meeting/event space Amenities: contemporary rooms, rooftop pool, five ... Experience working with servers and supporting table service preferred. Skills & Knowledge * Strong ...

Silver Diner Development, LLC

To-Go

Bethesda, MD · On-site

$15/hr

... our servers. They are also in charge of organizing the orders for online order and delivery services like Doordash and Uber Eats. * Make over $15 per hour. *Based on hourly wage+tips+tip pool ...

HRI Hospitality

234 rooms | 16,000 sq. ft. meeting/event space Amenities: contemporary rooms, rooftop pool, five ... Duties include communicating with Servers to determine their needs, carrying food items from the ...

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Pool Server information

See Maryland salary details

$5

$14

$29

How much do pool server jobs pay per hour?

As of Aug 9, 2026, the average hourly pay for pool server in Maryland is $14.84, according to ZipRecruiter salary data. Most workers in this role earn between $10.05 and $16.78 per hour, depending on experience, location, and employer.

What is a typical workday like for a pool server?

A typical day for a Pool Server involves greeting guests at the poolside, taking and delivering food and drink orders, setting up and maintaining the cleanliness of lounge areas, and responding promptly to guest needs. You’ll work closely with bartenders, kitchen staff, and other servers to ensure smooth service, especially during busy periods in warm weather. The work is mostly outdoors and requires being on your feet for extended periods, often in direct sunlight, so comfort with an active, dynamic environment is important. Many pool servers find the role lively and rewarding, with opportunities to earn tips and connect with guests in a relaxed, resort-like setting.

What is a pool server?

A Pool Server is responsible for taking food and drink orders and delivering them to guests at a poolside area, ensuring excellent customer service. They maintain cleanliness, restock supplies, and assist with guest requests to create a positive experience. Pool Servers must be attentive, efficient, and knowledgeable about the menu while working in an outdoor setting.

What are the key skills and qualifications needed to thrive in the pool server position, and why are they important?

To thrive as a Pool Server, you need strong customer service skills, a basic understanding of food and beverage service, and the physical stamina to work outdoors. Familiarity with POS (point-of-sale) systems and, in some locations, certifications such as a food handler’s permit or alcohol service license may be required. Excellent communication, teamwork, and the ability to remain calm under pressure are vital soft skills in this setting. These qualities ensure efficient, friendly service to guests in a fast-paced, outdoor environment, which is key for guest satisfaction and employer success.

What are popular job titles related to Pool Server jobs in Maryland? For Pool Server jobs in Maryland, the most frequently searched job titles are:
What job categories do people searching Pool Server jobs in Maryland look for? The top searched job categories for Pool Server jobs in Maryland are:
Pool Server jobs near you
Infographic showing various Pool Server job openings in Maryland as of August 2026, with employment types broken down into 70% Full Time, 25% Part Time, and 5% Contract. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $30,871 per year, or $14.8 per hour.

Room Service Server

Benchmark

Saint Michaels, MD • On-site

$13 - $16.75/hr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 22 days ago

Job description

Pyramid Global Hospitality is a leading hospitality management company with a portfolio of more than 200 hotels and resorts and over 18,000 associates across the United States, Caribbean, and Europe. Our platform includes Benchmark Resorts & Hotels, a collection of distinctive independent properties; Axiom Hospitality, our European hotel management company; and PYRAMIDWORKS, which provides integrated workplace and facilities services. With corporate offices in Boston, The Woodlands, Texas, and London, Pyramid combines global scale with a hands-on approach focused on exceptional service, operational excellence, and long-term partnerships.


At Pyramid, our people are at the heart of everything we do. We are committed to creating an environment where associates are respected, supported, and empowered to grow their careers. Team members have the opportunity to collaborate directly with experienced leaders, take on meaningful stretch assignments, and gain exposure to a diverse portfolio of properties, brands, and markets. Whether you are beginning your hospitality career or bringing years of experience, you'll find opportunities to learn, develop, and make an impact.


Our commitment to associates, guests, owners, and the communities we serve has helped make Pyramid and our properties among the most recognized in hospitality. From being named among the best places to work by respected publications such as USA Today, The Boston Globe, and The Houston Chronicle to earning top travel accolades from Travel + Leisure, Conde Nast Traveler, Forbes Travel Guide, and U.S. News & World Report, these recognitions reflect the culture, service excellence, and commitment to people that define the Pyramid experience.

About our property:

We invite you to become part of our crew at one of the most desirable destinations on the Eastern Shore, the Inn at Perry Cabin.
A Forbes 4-star historical gem tucked away on acres of privacy along the serene Miles River in St. Michaels, Maryland, the Inn at Perry Cabin encompasses genuine hospitality with a strong sense of nautical heritage. Our luxury resort provides a unique and authentic Chesapeake Bay experience and has been recognized as a top resort in the Mid-Atlantic by Conde Nast and Travel + Leisure. Providing upscale amenities such as Links at Perry Cabin (our exclusive Pete Dye-designed golf course), the Spa at Perry Cabin (our therapeutic oasis), and a Fleet of five sailboats, including the historic 1902 Skipjack, Stanley Norman, and a stately 55-foot Hinckley Yacht, Inn at Perry Cabin is one of the most desirable and unforgettable places to work on the Eastern Shore. Adding to the charm of the resort is a zero-edge swimming pool, lush gardens maintained by our on-property horticulturist, complementary bicycles, kayaks and paddleboards, and a unique array of resort activities. As a member of our crew, you will work with the BEST. Our team of diverse and passionate professionals enjoy an environment that fosters growth and encouragement in all they do. Our culture is supported by our Pillars: Service, Teamwork, Professionalism & Respect, Integrity, and Delivering Results. Our INN Crew share the goal of providing exceptional service and creating lasting memories for all guests of the Inn. If you are ready to set sail into a new adventure, apply today and enjoy the many benefits and great opportunities for growth at Inn at Perry Cabin! For more information about the Inn at Perry Cabin, please visit our website at innatperrycabin.com At Pyramid Global Hospitality, we are committed to caring for our team members by offering a comprehensive benefits package for full-time employees. Our benefits include medical insurance with employer contribution, as well as vision, dental, life, pet, and accident insurance options. We also provide a 401(k) program with an employer match and immediate full vesting, along with paid time off. Plus, all employees, including part-time team members, enjoy exclusive discounts across our portfolio of hotels. Join our team and experience the support, flexibility, and benefits that help you thrive both professionally and personally. *

What you will have an opportunity to do:

We are looking for a highly motivated, customer focused Room Service Server to join our team! Room Service is responsible for taking guests' orders over the phone and delivering food & beverage to guest rooms. They are responsible for ensuring accurate food orders as well as timely delivery.

If making meaningful connections, figuring out what it takes and stepping it up to win the day is what you do, and you love it, we want you! This is a tremendous opportunity for a driven person to grow and learn at a world-class property!

Your role:

  • Be thoroughly familiar with the menus, ingredients, and methods of preparation for each dish, wine list, as well as hours of operation for all food and beverage outlets.
  • Has a thorough knowledge of the room layout and the property in general. Is knowledgeable about the hotel and its amenities.
  • Collects orders from the kitchen, ensuring they have been prepared correctly; and promptly and efficiently deliver to the guest's room.
  • Will submit signed checks and reconciling daily sales
  • Assists with the collection of Room Service trays and other food and beverage items from the guest rooms. This also includes proper breakdown of trays and other items.
  • Be thoroughly familiar with all standards of proper service etiquette and will practice these standards throughout the guests dining experience.
  • Consistently delivers courteous, professional service.
  • Maintains high standards of cleanliness (personal appearance, equipment, and facility) always.

What are we looking for?

  • Someone with an engaging and welcoming personality
  • Someone with 2-4 years of food service experience
  • Someone with knowledge of wine, beer, cocktails, and spirits
  • Someone who can work under pressure in a fast-paced environment
  • Someone with a passion for creating an exceptional experience for all guests
  • Someone with excellent communication skills

Compensation:

$4.25

-

$4.25

Pyramid Global Hospitality is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Actual compensation packages are based on a wide array of factors unique to each candidate, including but not limited to skill set, years & depth of experience, certifications and specific office location. This may differ in other locations due to cost of labor considerations.

Apply