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Vacation Rental Operations Manager Jobs in Naples, FL

VTrips

Sales Executive

Fort Myers Beach, FL

$50K/yr

VTrips is a leading vacation property management company based in Ponte Vedra, FL. We specialize in providing exceptional vacation rental experiences for our guests and maximizing the rental income ...

VTrips

Sales Executive

Fort Myers Beach, FL · On-site

$50K/yr

VTrips is a leading vacation property management company based in Ponte Vedra, FL. We specialize in providing exceptional vacation rental experiences for our guests and maximizing the rental income ...

Better Talent

Property Manager

Fort Myers Beach, FL

$50K - $65K/yr

We are a vastly growing vacation rental, property management, and Real Estate company Fort Myers Beach, FL where the sun always shines. Our team members are the true soul of our company. Here at Sun ...

Allied Universal

Security Operations Manager

Naples, FL · On-site

As an Operations Manager, you will manage onsite Account Managers to ensure client satisfaction and ... Vacation time offered at an accrual rate of 3.08 hours biweekly. Unused vacation is only paid out ...

Hertz

Operations Research Analyst

Estero, FL · On-site

$75K/yr

Knowledge of AWS, S3, Databricks, Gurobi, Athena, supply chain operations, fleet management, or car rental operations is a plus * Passion for solving complex problems through mathematical reasoning ...

Career Search

Guest Service Agent

Fort Myers Beach, FL

$14 - $17.75/hr

We are a vastly growing vacation rental, property management, and Real Estate company Fort Myers Beach, FL where the sun always shines. Our team members are the true soul of our company. Here at Sun ...

Career Search

Guest Service Agent

Fort Myers Beach, FL · On-site

$14 - $17.75/hr

We are a vastly growing vacation rental, property management, and Real Estate company Fort Myers Beach, FL where the sun always shines. Our team members are the true soul of our company. Here at Sun ...

VRM Florida OpCo LLC

Property Caretaker

Marco Island, FL · On-site

$18 - $20/hr

... vacation rental properties with responsibilities including all aspects of property management ... Assists in the daily operations of the assigned portfolio of homes. Identify areas for improvement ...

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All JobsVacation Rental Operations JobsVacation Rental Operations Manager JobsVacation Rental Operations Manager Jobs in Naples, FL

Vacation Rental Operations Manager information

See Naples, FL salary details

$22.6K

$53.7K

$97K

How much do vacation rental operations manager jobs pay per year?

As of Sep 1, 2026, the average yearly pay for vacation rental operations manager in Naples, FL is $53,670.00, according to ZipRecruiter salary data. Most workers in this role earn between $42,400.00 and $59,300.00 per year, depending on experience, location, and employer.

What does a vacation rental operations manager do?

A Vacation Rental Operations Manager oversees the day-to-day operations of short-term rental properties, ensuring a seamless guest experience and efficient property management. Their responsibilities include coordinating cleaning and maintenance, managing guest check-ins and check-outs, handling guest inquiries or issues, and ensuring properties meet quality and safety standards. They also work with property owners, manage bookings, and may supervise staff. The goal is to maximize occupancy rates, guest satisfaction, and property profitability.

What are the key skills and qualifications needed to thrive as a vacation rental operations manager, and why are they important?

To thrive as a Vacation Rental Operations Manager, you need expertise in property management, hospitality operations, and customer service, often supported by experience in hospitality or real estate and a relevant degree or certification. Familiarity with property management systems (PMS), booking platforms like Airbnb or Vrbo, and maintenance scheduling tools is typically required. Exceptional organizational skills, problem-solving ability, and strong interpersonal communication help you excel in coordinating teams and ensuring guest satisfaction. These competencies are essential for maintaining high occupancy rates, positive guest experiences, and efficient, profitable operations.

What are some common challenges vacation rental operations managers face, and how can they be addressed?

Vacation Rental Operations Managers often navigate challenges such as coordinating housekeeping schedules, ensuring property maintenance, and managing guest expectations. High season periods can bring increased workloads, requiring efficient time management and clear communication with staff and vendors. Addressing these challenges involves implementing robust scheduling systems, establishing clear standard operating procedures, and fostering strong relationships with service providers. Proactive communication with guests and quick resolution of issues also contribute to smooth operations and positive guest experiences.

What is the difference between Vacation Rental Operations Manager vs Vacation Rental Property Manager?

AspectVacation Rental Operations ManagerVacation Rental Property Manager
CredentialsExperience in operations, hospitality, or property management; certifications like CAM or CMPReal estate license or property management certifications often preferred
Work EnvironmentOversees multiple properties, manages staff, and handles operational strategiesManages individual or multiple properties, focusing on day-to-day tenant or guest relations
Employer & Industry UsageUsed by property management companies, hospitality firms, and vacation rental platformsCommonly used by property owners, real estate agencies, and rental platforms

While both roles involve managing vacation rental properties, the Vacation Rental Operations Manager focuses on overall operations, staff management, and strategic planning across multiple properties. In contrast, the Vacation Rental Property Manager typically handles daily guest interactions, maintenance, and tenant relations for specific properties.

What are popular job titles related to Vacation Rental Operations Manager jobs in Naples, FL?

For Vacation Rental Operations Manager jobs in Naples, FL, the most frequently searched job titles are:

What job categories do people searching Vacation Rental Operations Manager jobs in Naples, FL look for?

The top searched job categories for Vacation Rental Operations Manager jobs in Naples, FL are:

What cities near Naples, FL are hiring for Vacation Rental Operations Manager jobs?

Cities near Naples, FL with the most Vacation Rental Operations Manager job openings:

Vacation Rental Operations Manager jobs near you
Infographic showing various Vacation Rental Operations Manager job openings in Naples, FL as of August 2026, with employment types broken down into 83% Full Time, 14% Part Time, 1% Temporary, 1% Contract, and 1% Nights. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $53,670 per year, or $25.8 per hour.

Senior Vacation Specialist

Fort Myers Beach, FL

Better Talent
Traveler Accommodation • 11 - 50 employees
Learn more about Better Talentexternal

Full-time

PTO

Re-posted 4 days ago

Job description

Company Overview

Coastal Vacation Properties is the Premier Vacation Property Management Company in Fort Myers Beach. A family-owned business, we’ve become successful by personalizing the needs of our clients. We offer competitive wages, bonus opportunities, and paid time off. 

For over 25 years, we have managed preferred vacation rental homes of all sizes, from condos to large multi-family luxury beach homes. Our success is in prioritizing our guests' experience and working diligently to grow our vacation rental homeowners' businesses with professionalism, relationship building, and effective marketing.

Position Summary

We are seeking an experienced, motivated Senior Vacation Specialist to support our growing reservations department. This is a hybrid role combining reservation specialist responsibilities with leadership development opportunities.

The ideal candidate is highly organized, guest-focused, and experienced in vacation rental or hospitality operations. This role will begin with a primary focus on reservations and guest service, allowing the candidate to become fully familiar with our systems, portfolio, and operational procedures. As experience and familiarity with our operations grow, the position will gradually expand to include leadership responsibilities within the department.

Our team is committed to maintaining the highest level of service and professionalism, and we’re looking for someone who can lead by example while supporting both guests and fellow team members.

Key Responsibilities

Reservation Specialist Duties

  • Manage reservations, including payments, documentation, check-in instructions, and guest communication

  • Respond to guest inquiries across all booking channels (direct, Airbnb, Vrbo, and other OTAs)

  • Answer incoming phone calls and emails from guests and property owners

  • Assist guests with booking questions, stay requests, and issue resolution

  • Monitor and respond to guest reviews

  • Coordinate with housekeeping, operations, and quality control regarding reservation updates or guest concerns

  • Assist with onboarding and setup of new rental properties

Leadership & Department Oversight (assumed after training and operational familiarity)

  • Train and mentor Vacation Specialist team members on systems, policies, and procedures

  • Manage all HOA/Condo paperwork submittal

  • Monitor team performance, productivity, and guest communication quality

  • Manage department coverage

  • Conduct one-on-one check-ins and assist with performance evaluations

  • Provide coaching on call handling and guest service standards

  • Assist with handling escalated guest concerns, refund requests, and disputes

  • Review reservation correspondence to ensure accuracy and professionalism

  • Maintain reservation procedures and identify opportunities to improve workflow efficiency

  • Help create and maintain Standard Operating Procedures (SOPs) for reservation processes

  • Monitor booking accuracy and assist in resolving issues such as double bookings or guest relocations

Reporting & Performance Monitoring

  • Track weekly booking performance

  • Monitor call volume, response times, and inquiry conversion

  • Review guest disputes and refund requests

  • Identify booking errors and ensure proper documentation and notes are maintained

Required Qualifications

  • 1+ years minimum previous experience in vacation rentals, hospitality, or property management

  • Experience with reservation systems (Streamline PMS preferred)

  • Strong leadership, communication, and problem-solving skills

  • Highly organized with strong attention to detail

  • Ability to multitask and adapt in a fast-paced environment

  • Tech-savvy and comfortable learning new systems and software

  • Team-oriented with a positive, professional attitude

  • Ability to work Monday–Friday with occasional on-call or weekend coverage

Preferred Qualifications

  • Bilingual preferred but not required

Compensation, Benefits, & ScheduleHourly Salary

  • 21-22

Benefits

  • Paid time off such as PTO, sick days, and vacation days

Schedule

  • Monday-Friday, On-call shifts as needed