posted September 15, 2025

Security Supervisor

Apply Now
Save this job

Compensation: N/A

Job Description

Security Supervisor – Cheeca Lodge & Spa

? Islamorada, FL – Flexible Shifts


Join Our Team of Dedicated Hospitality Professionals

Cheeca Lodge & Spa is seeking an experienced and motivated Security Supervisor to lead our safety and security efforts across our resort property. This key leadership role ensures a safe environment for our guests, employees, and facilities by overseeing patrol operations, responding to incidents, maintaining reports, and working closely with local law enforcement partners.

? Position Overview

As Security Supervisor, you will provide hands-on leadership during your shift, support daily security operations, and help maintain Cheeca's reputation for safety and guest satisfaction. You will also help train team members, respond to emergencies, and ensure compliance with applicable laws and resort policies.

? Key Responsibilities

  • Patrol the property to ensure the safety of guests, staff, and resort assets

  • Supervise Security Officers and ensure proper shift coverage

  • Respond promptly to incidents, disturbances, or emergencies

  • Write detailed and accurate security reports

  • Support investigations and follow-up on guest or employee concerns

  • Coordinate with local law enforcement as needed

  • Promote safety awareness among staff and guests

  • Ensure all security activities align with Florida statutes and resort protocols

  • Participate in safety and CPR/First Aid training

What You Bring

Required Qualifications:

  • Prior supervisory experience in hospitality or resort security

  • Excellent communication skills and professional demeanor

  • Strong knowledge of security practices, report writing, and Florida law

  • Clear driving record and valid driver’s license

  • CPR and basic first aid certified (or willing to obtain)

  • Fluent in English; bilingual (Spanish or Creole) preferred

  • Flexible availability – must be able to work weekends and holidays

  • Strong physical condition – must be able to walk, stand, lift, and respond actively across the resort property

  • Ability to work in variable weather conditions (heat, rain, wind, etc.) and noisy environments

Why Work at Cheeca Lodge & Spa?

  • Join a Four-Diamond resort team that takes pride in service excellence and community partnerships

  • Work in a beautiful oceanfront environment in the Florida Keys

  • Enjoy competitive pay and employee benefits for full-time roles

  • Free shift meals

✨ Apply Today

Be a part of something bigger — help protect paradise. Apply now for the Security Supervisor role at Cheeca Lodge & Spa, and take your career in hospitality and security to the next level.

Apply Now
Save this job

Cheeca Lodge and Spa

Hotel with 214 Rooms

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.

Logo for Cheeca Lodge and Spa

81801 Overseas Highway

Islamorada, FL 33036

Website www.CheecaJobs.com

Managed by Northwood Hospitality

Current Job Openings
Print a jobs flyer