Vacation Rental Operations Manager
Fort Myers / Cape Coral, Florida | Full-Time | Local Position
iTrip Cape Coral/Fort Myers is seeking an experienced, highly organized and guest-focused Vacation Rental Operations Manager to oversee the day-to-day field operations of our vacation rental properties throughout the Cape Coral and Fort Myers market.
The primary focus of this role begins as our guests prepare to arrive and continues throughout their stay—ensuring properties are guest-ready, responding to in-stay needs, coordinating maintenance and vendors, resolving issues and protecting the overall quality of the guest and owner experience.
The manager would work and be based out of their home as they do not report to an office. However, the ability to drive and travel to properties within the portfolio is a priority within this position.
We are looking for someone who takes ownership, communicates well and understands that in vacation rental operations, identifying a problem is only the beginning - the job is making sure it gets resolved.
A Cape Coral resident is STRONGLY PREFERRED BUT NOT REQUIRED as most of the portfolio is located throughout Cape Coral with some properties in Fort Myers.
Job Responsibilities
Property & Field Operations
· Oversee day-to-day operations for a portfolio of vacation rental homes and condos throughout Fort Myers and Cape Coral.
· Conduct and/or coordinate pre-arrival property inspections to ensure homes are clean, properly prepared and ready for incoming guests.
· Identify maintenance, housekeeping or property condition issues and coordinate timely resolution.
· Work closely with housekeeping teams, maintenance technicians, contractors and other service vendors.
· Verify completed work rather than assuming a service call means the problem has been resolved.
· Monitor open maintenance and operational issues and follow them through to completion.
· Help maintain consistent property standards across the portfolio.
· Perform periodic property inspections and report concerns regarding maintenance, condition, inventory or owner attention.
Guest Relations – After Arrival
· Serve as a primary point of contact for guests experiencing property-related issues during their stay.
· Respond promptly and professionally to maintenance concerns, housekeeping issues, access problems and other in-stay needs.
· Display and perform a high level of customer service communication with vacation rental guests, sometimes under difficult circumstances.
· Troubleshoot problems and determine the appropriate solution, vendor or next step.
· Communicate clearly with guests throughout the resolution process so they know their concern is being addressed.
· Recognize when an issue requires escalation to management.
· Help turn unexpected vacation problems into positive guest experiences whenever possible.
Vendor & Maintenance Coordination
· Dispatch and coordinate appropriate vendors for repairs and service needs.
· Build productive working relationships with local service providers.
· Follow up on outstanding work orders and confirm completion.
· Help prioritize urgent guest-impacting issues versus repairs that can appropriately be scheduled after departure.
· Document maintenance concerns, completed work and important property information.
· Communicate significant property issues and recommendations to management for owner follow-up when appropriate.
Qualifications
The right candidate will be:
· Highly organized and able to manage multiple open issues at the same time.
· Comfortable working independently and making sound decisions in the field.
· Guest-focused without losing sight of the owner's property and business interests.
· Calm and professional when dealing with frustrated guests or unexpected situations.
· An excellent communicator with guests, owners, coworkers and vendors.
· Detail-oriented and observant during property inspections.
· MUST KNOW how to use mobile apps, ability to learn, navigate and understand property management software, regularly accessing, using and responding professionally to text messages and emails, along with digital work-order systems.
· Someone that owners can trust when they can contact YOU, not your superiors, and their homes are being watched over carefully.
· Reliable and accountable with strong follow-through.
· Familiar with Cape Coral, Fort Myers market and the surrounding Southwest Florida area.
Experience
Previous experience in vacation rental operations, hospitality operations, property management, or a closely related field is strongly preferred.
Experience coordinating maintenance, housekeeping, contractors or field service teams is highly desirable.
Vacation rentals operate differently from traditional long-term property management, so experience working with short-term rental guests and the fast turnaround between stays is especially valuable.
Schedule & Availability
This is a full-time, local position and requires regular travel throughout primarily the Cape Coral market, along with additional properties in Fort Myers.
Because vacation rentals operate seven days a week, candidates must be available to work weekends and holidays and respond to time-sensitive operational situations.
This position requires being accessible and available 6 days/week with the day off in the middle of the week.
This is not a traditional Monday-Friday, 9-to-5 position.
Physical & Transportation Requirements
Candidates must have a valid driver's license, reliable transportation and the ability to travel between properties throughout Cape Coral and Fort Myers.
The position requires regular walking, standing, climbing stairs and inspecting residential properties, as well as the ability to perform reasonable light physical tasks associated with preparing and inspecting vacation rentals.
Salary
Starting salary range $50,000-$53,000 + Seasonal Bonus
Paid Time Off (10 vacation days, 5 sick days) – Vacation Days cannot be used during major holidays or peak-season (December-April) as that is the busiest time in vacation rental throughout SWFL.
Pay: $50,000.00 - $53,000.00 per year
Benefits:
Work Location: Remote
