The Islands of Islamorada is a secluded luxury boutique resort nestled along a pristine stretch of the Upper Florida Keys.

Featuring 22 spacious four-bedroom oceanfront villas and eight elegant one-bedroom suites, the property offers a

private sanctuary of refined island living. Guests enjoy two oceanfront pools, a private beach, marina with boat slips,

pickleball courts, fitness center, and personalized concierge services—all set against crystal-clear waters and the laid-

back elegance of Islamorada, the Sportfishing Capital of the World.

KEY RESPONSIBILITIES:

Operations Management

• Manage and supervise front desk, concierge, and guest services operations to deliver seamless check-in/check- out experiences and exceptional service standards consistent with The Islands of Islamorada’s luxury positioning.
• Oversee daily front office operations including reservations coordination, room assignments, billing accuracy, and special request fulfillment across villas and suites.
• Ensure security and safety protocols and property access standards are consistently enforced to maintain a safe, private environment for guests, owners, and team members.
• Coordinate closely with Housekeeping, Engineering, and Marina teams to support efficient villa and suite readiness and guest movement throughout the property.
• Ensure all incidental charges including F&B are accurately posted, reconciled and accounted for on a daily basis
• Ensure all Exclusive Resort and Inspirato standards are executed daily and ensure staff is held accountable for achieving

Guest Experience

• Uphold anticipatory, personalized service that reflects the resort’s exclusive, residential-style luxury experience; proactively address guest needs and preferences.
• Handle escalated guest concerns with professionalism and urgency, driving prompt resolution to protect and elevate satisfaction scores and online reputation.
• Collaborate with all departments (Housekeeping, Food & Beverage, Concierge, and Marina) to deliver cohesive, memorable guest journeys across the resort’s amenities.
• Manage VIP arrivals, special occasions, and loyalty recognition programs; ensure guest preferences are accurately captured and acted upon in the property management system.

Owner Relations

• Serve as a primary point of contact and trusted partner for villa owners, fostering strong, professional relationships built on transparency, responsiveness, and care.
• Coordinate owner arrivals, stays, and special requests with the same elevated standards applied to hotel guests; ensure seamless communication between owners, operations, and leadership.
• Act as primary owner liaison and meet property performance expectations while coordinating property services, and resort initiatives in partnership with leadership and any third-party management or sales partners.
• Maintain accurate records of owner preferences, contacts, and stay history; resolving owner conflicts and appropriately escalating ownership-related issues as needed, promptly and professionally.
• Ensure billing, maintenance requests, property services and all owner charges are managed timely and accurately to exceed owner expectations

Staff Management

• Recruit, train, coach, and mentor front office and guest relations team members, fostering a diverse, inclusive, and service-driven culture.
• Develop and manage schedules that balance operational coverage with team member work-life balance in a high-touch, villa-centric environment.
• Implement ongoing training focused on luxury service standards, systems proficiency, conflict resolution, and owner-guest interaction protocols.

Operational Efficiency & Compliance

• Monitor departmental performance against budgets and labor targets while upholding luxury service standards.
• Oversee front office systems (PMS, reservation platforms, and related tools) and ensure data integrity, accurate billing, and system reliability.
• Ensure compliance with resort policies, safety standards, accessibility requirements, and all applicable regulations.

Performance Metrics

• Track and analyze key performance indicators including guest satisfaction scores, online review ratings, occupancy metrics, and departmental contribution.
• Review and respond within 24 hours to feedback from all 3rd party sites including Tripadvisor, Google, as well as internal surveys, and direct guest/owner comments to identify trends and drive continuous improvement
• Strive to be the property expert on all guest related front office systems and train staff to meet service expectations

QUALIFICATIONS:

• Bachelor’s degree in hospitality management, business administration, or a related field preferred; equivalent experience considered.
• Minimum of 4–6 years of progressive experience in hotel/resort front office or guest relations operations, with at least 2–3 years in a supervisory or managerial capacity.
• Proven leadership experience managing teams in a high-touch, luxury, or residential-style hospitality environment; villa, condo-hotel, or owner-relations experience strongly preferred.
• Strong working knowledge of property management systems (PMS), front office operations, revenue awareness, and guest preference management.
• Exceptional communication, relationship-building, problem-solving, and interpersonal skills; ability to interact confidently with owners, VIP guests, and internal stakeholders.
• Familiarity with the Florida Keys market and luxury traveler expectations is a plus.
• Ability to work flexible hours, including evenings, weekends, and holidays, in a fast-paced, guest-facing leadership role.

Work Environment:

Boutique luxury resort setting in Islamorada, Florida Keys. This position offers a beautiful island location with access to resort amenities (based on availability) and meaningful professional growth opportunities.

BENEFITS:

• Competitive salary
• Medical, dental, vision, and ancillary benefits
• Potential discounts at sister properties
• Opportunities for professional development in a high-profile luxury resort
• Discounted employee meals during work shift

No Job Description for a position can possibly include all duties which may be requested by guests or required by the hotel. The objective of all positions is to effectively provide the services personally, or to immediately refer requests to the appropriate department manager. The items listed above are a summary of the major responsibilities of the position that must be met by an employee to successfully perform the essential functions of the position. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

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.

Visit us online at Islands of Islamorada Resort™ - Official Site - A Florida Keys Luxury Resort and explore our parent company, EOS Hospitality for more information about the amazing ways we’re making a difference.