Cheeca Lodge and Spa

81801 Overseas Highway

Islamorada, FL 33036

Website www.CheecaJobs.com

Managed by Northwood Hospitality

Hotel with 214 Rooms
Managed By Northwood Hospitality
Save this job
Full-Time

Job Description

Nestled among lush tropical foliage and just steps from the world-class amenities of Cheeca Lodge & Spa, the Casitas at Cheeca offer an unparalleled luxury escape in the heart of Islamorada. Designed to provide the privacy of a secluded residence with the elevated service of a premier resort, the Casitas deliver a bespoke guest experience defined by authentic hospitality, thoughtful attention to detail, and unforgettable moments. The Casitas feature luxurious one and two-bedroom residences, personalized butler service, curated guest experiences, and seamless access to the best of the Florida Keys.

The Casitas and VIP Guest Services Manager is responsible for leading this exceptional experience from start to finish. This role oversees all aspects of the Casitas operation and VIP guest journey, ensuring every residence is impeccably prepared and every guest interaction exceeds expectations. Through close collaboration with resort leadership and oversight of the Casitas Butler team, the Manager creates personalized, memorable stays through proactive pre-arrival planning, tailored guest experiences, seamless service delivery, and meaningful follow-up. As a key member of the Front Office Leadership Team, this individual serves as a champion of luxury hospitality, fostering a culture of excellence that reflects the elevated standards and warm island spirit of Cheeca Lodge & Spa.

Job Duties

  • Responsible for overseeing the daily operation of the Casitas at Cheeca Lodge
  • Maintains the quality and consistency of Casitas room product and property standards
  • Recruiting, training, management and retainment of Casita Butler team members
  • Ensure Cheeca VIP guest stays are well communicated and prepared for
  • Foster and maintain positive relations with guests and team members
  • Have a full understanding of Cheeca Front Office Leadership responsibilities
  • Perform Cheeca MOD duties as needed
  • Drive for results that support the vision and values of the company.
  • Accountabile for Casitas service scores and expenses
  • Create a positive work environment through training and communication
  • Demonstrate creative problem solving, personal initiative and independent motivation to achieve goals.
  • Cooridnate with Group Sales and Conference Services team to support execution of Casitas weddings and events
  • Demonstrate passion and excitement for hospitality
  • Provide superior guest service, assistance, and resolution via written, phone and direct face-to-face communication in response to guest related situations.
  • Prepare employee schedule according to business forecast and process Butler team member’s payroll
  • Develop and maintain all Casitas and VIP SOP’s.
  • Review and analyze monthly results, highlight trends and problem areas, and discuss these with the  Director of Rooms Operations and appropriate staff.
  • Ensure appropriate action is taken to proactively improve both Guest Experience and Casitas room product
  • Attend meetings and training courses as required; continually strive for the improvement of professional skills.
  • Motivate and inspire staff to apply guest service standards and policies that will distinguish Casitas at Cheeca from the competition.
  • Conduct performance evaluations. Coach and direct activities to achieve desired performance.

Required Qualifications:

  • Minimum 5 years of progressive experience in a hotel or a related field
  • Exceptional interpersonal and customer service skills
  • Excellent organizational and multi-tasking skills
  • Strong attention to detail
  • Effective written and verbal communication skills
  • Knowledge of Microsoft Office
  • Valid Driver License

Preferred Experience

  • Minimum 3 years of progressive experience in a luxury resort environment
  • Professional Butler or Household Management experience
  • Knowledge and proficiency in areas of hospitality housekeeping and engineering
  • Knowledge of local Florida Keys offerings and attractions

Physical Requirements

  • Ability to walk and stand for extended periods, talk, hear, listen, reach, grasp and perform repetitive motions
  • Ability to push, pull, lift, carry or otherwise move up to 40 - 60 lbs.

Benefits Include:

  • 401(k) with employer matching.
  • Employer Paid Short Term and Long Term Disability Insurance.
  • AD&D insurance.
  • Dental, health, and vision insurance.
  • Employee discounts.
  • Flexible spending and health savings accounts.
  • Life insurance.
  • 18 Days Paid time off

Why Join Cheeca Lodge & Spa: As the Casitas and VIP Guest Services Manager, you will play a key role in ensuring our guests have an exceptional experience. This role offers a dynamic work environment, professional growth opportunities, and the chance to lead a dedicated team in a prestigious resort setting. Join us to make a significant impact on our guests' experiences and elevate our service standards.

Posted August 10, 2026

About Cheeca Lodge and Spa

WELCOME TO CHEECA

A Legendary Tropical Hideaway

Since 1946 the historic Cheeca Lodge & Spa has enchanted guests with world-class fishing, exceptional accommodations, and gracious hospitality. Come experience this lush oceanfront retreat, considered the premier luxury resort in the Florida Keys.

The Legend of Our Grand Florida Keys Hotel Resort

You've found it...the crown jewel of Islamorada Florida Keys hotels. 

Hardy Keys pioneers called Conchs chose this very beach to carve out a tenacious living in the isolated beauty of the undiscovered Florida Keys. Here, they formed a Methodist congregation and built a two-room school house and a cemetery. Cheeca has preserved this Pioneer Cemetery, where members of the founding families of Islamorada are buried. You can explore it today; it is a designated historical site. The Angel with the Broken Wing watches over the grave of Etta Pinder, who died in 1914. Here lies the first footprint of Islamorada – "Purple Isle" in Spanish.

The early 1940's brought electricity and fresh water. Mrs. Clara Mae Downey from Olney, Maryland, opened the Olney Inn in 1946. She described this early bellwether of Cheeca as "different – rather comparable to the tropical estate of a gifted host." Clara's first guest was President Harry Truman, who cherished his time loafing around the pool and wondering amidst the resort's 22 quaint bungalows. 

Fast horses, high society and a healthy dose of Keys vivacity marked the reign of the Twitchell Family in the 1960's. Cynthia, better known as "Chee," was an heiress to the A&P grocery chain and owner of a top thoroughbred racing farm. "We took my nickname, combined it with my husband Carl's, and came up with "Cheeca," she recalled. The Twitchells completely refurbished the property, adding the main lodge, the oceanfront villas, tennis courts, golf course and Cheeca's trademark wooden fishing pier. Chee raised miniature tarpon and her beloved seahorses in the aquariums throughout the resort. "Suzy the Seahorse" became Cheeca's mascot and logo, gracing the resort's menus, brochures, towels and linens.

Avid outdoorsman and Coca Cola magnate Carl Navarre purchased Cheeca Lodge in 1976, hosting his Fortune 500 friends in for sunny days of sportfishing and golf. Celebrities flocked to the hotel and famous guests were reeling in giant bonefish right off the resort's pier. The "Sportfishing Capital of the World" was born, seducing wealthy adventurers from around the world.

In 2005, Cheeca Lodge underwent over $30 million dollars in renovations, restoring the property and its surrounding grounds to their original grandeur, ensuring that we will be a cherished destination for generations to come. Following a fire on New Year's Eve 2008, the Main Lodge was completely rebuilt once again, with a fabulous open-air lobby, a spectacular oceanfront banquet room with panoramic views, and an exclusive indoor / outdoor lounge area for club members.

About Northwood Hospitality

Founded in 2006, Northwood Hospitality (NWH) has established itself as a leading boutique operator with a true understanding of value creation. Our high-touch management philosophy focuses on providing a collaborative and hands-on approach with each hotel team. We rely on real-time operating data to drive both strategies and revenues.

People are our Passion

Our team members, guests, partners and our communities are our passion. We take a people-first approach to learning & developing, ensuring our team members have the skills and tools to succeed.

Our Purpose

Our purpose is to create and nurture an environment that ignites our team members passions; we provide the tools & mentoring to empower them and foster a sense of belonging.

Our Mission

Our mission is to maximize asset value creation and performance.

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