Property Manager

Historic Key West Annual Rentals

Property Manager

Key West, FL | Onsite

$65,000 to $80,000 + Bonus Opportunity

Historic Key West Annual Rentals is seeking an experienced Property Manager to oversee a portfolio of long term residential rental homes throughout the Florida Keys. This is an excellent opportunity for someone who enjoys building relationships, solving problems, and delivering exceptional service to both property owners and residents.

This role is based onsite in Key West and is best suited for candidates who already live in Florida, preferably in the Miami, Florida Keys, or surrounding South Florida area , and are excited to work in one of the country's most unique real estate markets.

What You'll Do

As the Property Manager, you'll serve as the primary point of contact for property owners, residents, and vendors while overseeing the day to day operations of a residential rental portfolio. Responsibilities include:

• Manage long term residential rental properties from lease execution through renewal and move out
• Build strong relationships with property owners and residents through responsive, professional communication
• Coordinate maintenance requests and vendor relationships while ensuring timely resolution of work orders
• Oversee property turnovers to minimize vacancy and maximize rental income
• Conduct property inspections and ensure homes are well maintained
• Prepare lease agreements, renewals, notices, and other property documentation
• Ensure compliance with Florida landlord tenant laws and Fair Housing regulations
• Utilize AppFolio Property Manager to manage leasing, maintenance, financial reporting, and resident communications

What We're Looking For

We're looking for someone who thrives in a fast paced environment and enjoys balancing customer service with strong operational execution.

Required Qualifications

• 2+ years of residential property management experience
• Active Florida Real Estate License or willingness to obtain one quickly
• Strong understanding of Florida landlord tenant laws
• Excellent communication and relationship building skills
• Highly organized with the ability to manage multiple priorities
• Valid Florida driver's license and reliable transportation

Preferred Qualifications

• Experience managing long term residential rental portfolios
• Experience with AppFolio Property Manager or similar property management software such as Buildium or Yardi
• Apartment community management experience

What Makes Someone Successful

The ideal candidate is proactive, organized, and service focused. They understand how to advocate for property owners while creating a positive resident experience. They are comfortable managing multiple priorities, making sound decisions, and working collaboratively with a close knit team.

Location Requirement

This is an onsite position based in Key West, Florida .

Candidates must currently reside in Florida . Preference will be given to candidates living in Key West, the Florida Keys, Miami, or surrounding South Florida communities who understand the local market and are committed to building a long term career in the area.

If you're passionate about property management and are looking for an opportunity to make a meaningful impact while working in one of Florida's most distinctive communities, we'd love to hear from you.