Long Term Rental Management Services

For over 20 years, Historic Key West Annual Rentals has been the market-leading annual, long-term rental and property management company in Key West. Our core focus is our partnership with property owners and exceeding their service expectations and investment goals. We have the experience and staff to service your property and garner market leading revenue.

Contact Misty Walser today to learn more about our services and how they can be tailored to fit your needs.

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Why Choose Us

Attention to Detail. Each of our leases are attorney prepared. We video record your property before tenants move in and conduct annual inspections.

Tenant Screening. Exceptional tenant screening process that includes credit, eviction, and background check, landlord and employment references. Resident guarantee policy - if our resident breaks their lease in the first six months, we'll waive our leasing fee and re-rent your property at no charge to you!

Helpful Staff. Our people make the difference! Over 20 years of experience and highly trained, licensed and insured full-time professionals. On-call 24/7 emergency services.

Online Owner Portal. We use the industry's best property management software. Through your secure Owner's Portal, you can review all your financials online. Direct deposit of your rental income goes right into your bank account!

Maintenance Staff. You can complete any needed maintenance yourself or let us do it and you deduct it from your taxes! We will help you preserve the value of your property and look after your investment.

Exceptional Service! Communication is everything. We will keep you informed every step of the way. From getting your home ready for rental and maintenance issues to financials. Our office is locally-owned and operated, and we are here for you!

Our Property Management Services

Caretaking Services.


EXTERIOR

  • Visual inspection of all exterior walls, windows, and roof for damages.
  • Landscaping: Inspect for downed limbs or damages. Bring in garbage cans.
  • Pool: Check pool equipment, check pool water level and add water if needed.


INTERIOR

  • Check all windows/doors to verify locked.
  • Visually inspect ceilings/walls/floors for water intrusion and pests.
  • Adjust AC thermostat to verify unit is running and turning off correctly.
  • Kitchen: Run dishwasher rinse cycle, check fridge & freezer for temperature, check wine cooler. Run water in sinks and run garbage disposal.
  • Bathrooms: Flush all toilets, run water in sinks and showers.


OTHER

  • Vehicles: Start vehicles, run for 5 minutes.
  • Mail: Pick up mail and send to owner mailing address (mailing fee is an additional charge).


CARETAKING FEES

Contact us for Pricing and Scheduling

Management Operations.  Property management operations involve overseeing the day-to-day activities related to managing a property or a portfolio of properties. It encompasses a broad range of tasks designed to ensure that the property runs smoothly, is well-maintained, and meets both the needs of tenants and the goals of property owners. Here’s a breakdown of key aspects:


1. Tenant Management

  • Tenant Acquisition: This involves advertising the property, conducting showings, screening tenants (background checks, credit checks, rental history, etc.), and signing leases.
  • Lease Management: Ensuring leases are current, renewing leases, handling rent increases, and ensuring tenants comply with lease terms.
  • Tenant Relations: Addressing tenant complaints, managing communication, and ensuring tenant satisfaction. Happy tenants are more likely to renew leases.


2. Financial Management

  • Rent Collection: Setting up efficient systems for collecting rent, handling late payments, and enforcing penalties when needed.
  • Budgeting: Creating budgets for maintenance, staffing, utilities, insurance, and other property expenses.
  • Financial Reporting: Keeping track of income and expenses, creating regular reports for the property owner, and ensuring profitability.


3. Property Maintenance & Repairs

  • Routine Maintenance: Ensuring that the property is well-maintained through regular inspections, cleaning, and preventative maintenance (e.g., HVAC checks, plumbing inspections).
  • Repairs: Handling emergency repairs, tracking work orders, and coordinating with contractors and maintenance staff.
  • Upgrades and Renovations: Managing any larger projects, like remodeling units or upgrading facilities to increase property value or appeal.


4. Legal Compliance

  • Fair Housing Laws: Ensuring that the property complies with local, state, and federal housing laws, including anti-discrimination laws, safety codes, and tenant rights.
  • Evictions: Handling legal eviction processes in cases of non-payment or lease violations, following the proper legal steps.


5. Marketing and Leasing

  • Advertising: Creating listings on websites, social media, or using other marketing channels to attract potential tenants.
  • Lease Negotiations: Negotiating terms of the lease with tenants, including rent prices, lease duration, and other specific clauses.


6. Technology & Systems

  • Property Management Software: Many property managers use software to streamline rent collection, maintenance requests, and financial reporting. Some systems also allow for online tenant portals.
  • Automation: Automating payment reminders, rent collection, and tenant communications to improve efficiency.


7. Risk Management & Insurance

  • Insurance: Ensuring the property is adequately insured for risks such as fire, flooding, liability, etc.
  • Risk Mitigation: Taking steps to prevent incidents like accidents, injuries, or damages (e.g., maintaining smoke detectors, ensuring proper lighting in common areas).


8. Vendor Management

  • Contracting Services: Hiring contractors for specialized tasks like landscaping, cleaning, or pest control.
  • Vendor Relationships: Building strong relationships with reliable vendors to ensure quick responses and quality service when needed.
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