The Ultimate STR Property Management Checklist for First-Time Investors

Managing a short-term rental sounds glamorous — until you’re fielding a 10 p.m. call about a broken A/C… from three time zones away.

Whether you’re just launching your first Airbnb or transitioning from long-term rentals, success in short-term rental (STR) management boils down to one thing:

Systems.

And those systems start with a rock-solid checklist.

This guide is your go-to reference for what every first-time STR investor should have in place — from tech and tools to cleaning standards, guest communications, and legal compliance.

Let’s make sure you’re covered.

🧰 1. Set Up Your STR Tech Stack

Your property can’t run smoothly without tech — especially if you’re not on-site. Here’s your must-have software suite:

✅ Booking & Channel Manager

• Airbnb

• VRBO

• Optional: Direct booking site via Hostfully or Hospitable

✅ Dynamic Pricing Tool

• PriceLabs, Beyond, or Wheelhouse

✅ Property Management System (PMS)

• Manage calendars, guest messaging, payments, and reviews

• Examples: Guesty for Hosts, Hostaway

✅ Cleaning + Task Scheduling

• Breezeway, Turno

✅ Automation Tools

• Auto-messaging, check-in instructions, upsells

• SMS alerts, smart locks, review requests

Pro tip: Don’t wait until you have multiple properties to build your stack. Start smart, then scale.

🧽 2. Build a Cleaning and Inspection System

Cleanliness is non-negotiable. STR guests expect hotel-level consistency — and they’ll absolutely mention it in reviews.

✅ Cleaning Checklist (room-by-room)

• Bedrooms: linens, mattress protectors, nightstands, under beds

• Bathrooms: behind toilets, shower curtains, restocked supplies

• Kitchen: all appliances, drawers, trash bins

• Living: TV remotes, light switches, coffee tables

• Exterior: entry area, patio, furniture wiped down

✅ Quality Control Checklist

• Final walk-through after every clean

• Inventory restock (toilet paper, paper towels, soap, etc.)

• Report damages or missing items

• Photo documentation of each turnover

📥 Download our free STR Cleaning & Inspection Template

Consider: Hiring a dedicated inspector or training your cleaner to double-check every clean.

📱 3. Standardize Guest Communication

Great guest communication = fewer bad reviews, faster issue resolution, and higher rebooking rates.

✅ Set up automated message templates:

• Booking confirmation

• Pre-arrival welcome + directions

• Check-in instructions

• Mid-stay check-in (“Hope everything is perfect!”)

• Checkout reminder + review request

✅ Bonus Tips:

• Add local recs + hidden gems in your welcome email

• Use SMS backup for emergency access

• Set response time goals: under 1 hour during waking hours

Tools to use: Hospitable, Hostaway, or native Airbnb automation features.

🛠️ 4. Prep for Maintenance and Emergencies

Something will break. The question is whether you’re ready for it.

✅ Your STR Maintenance Toolkit:

• Plumbing contact (available weekends)

• HVAC company (that does emergency calls)

• Electrician (for outages or code issues)

• Handyman (for minor repairs)

• Lawn + pool care team (if applicable)

• Pest control (especially in humid markets like Florida)

Maintenance plan:

• Schedule bi-monthly or quarterly walks

• Keep filters, light bulbs, batteries stocked

• Review maintenance checklist every month

🔗 Want to outsource maintenance? Read how full-service PMs handle it here

📋 5. Handle Legal and Financial Compliance

The not-so-fun stuff… but the essential stuff.

✅ Licensing & Registration

• STR license with city or county

• State sales tax registration

• Tourist development tax (especially in FL)

✅ Insurance

• STR-specific policy (not just homeowner’s)

• Liability coverage of $1M+

• Consider supplemental Airbnb/VRBO protection

✅ Accounting

• Separate business account (LLC preferred)

• Track income/expenses monthly

• Save 25–30% for taxes

• Tools: QuickBooks, Stessa, or CPA

Helpful Tip: Florida investors — don’t forget to register with Florida Department of Revenue for sales tax collection.

🎯 6. Optimize for Performance

Once you’re live, the name of the game is revenue per available night (RevPAN) — not just occupancy.

✅ Pricing Best Practices:

• Use a dynamic pricing tool from Day 1

• Update minimum stays seasonally

• Adjust pricing based on local events

✅ Calendar Management:

• Keep your calendar synced across platforms

• Avoid double bookings (PMS helps here)

• Use “orphan night” strategies to fill 1-2 night gaps

✅ Monitor Reviews and Performance:

• Weekly review check-ins

• Flag any guest complaints or patterns

• Celebrate wins — and apply guest feedback

🔗 Check out our post: What Top 10% STRs Do Differently

🧠 7. Set Up for Scale

If your goal is to own more than one STR, build scalable systems from the start.

✅ Things to Automate:

• Smart lock codes

• Auto-messaging sequences

• Cleaner task assignments

• Tax and income reporting

✅ Things to Delegate:

• Guest messaging (VA or PM)

• Maintenance requests (on-call handyman)

• Inspections (local rep or inspector)

The more you can remove yourself from daily operations, the more you can focus on deal flow, funding, and growth.

🔄 Quick Reference: The Ultimate Checklist

🧰 Operations

✔ PMS
✔ Dynamic Pricing Tool
✔ Cleaner Scheduling Platform
✔ Booking Channel Sync

🧼 Turnovers

✔ Cleaning Checklist
✔ QC Inspections
✔ Inventory Tracking
✔ Guest Essentials Restocked

💬 Guest Experience

✔ Message Templates
✔ Local Guidebook
✔ Emergency Contact Info
✔ Review Strategy

🧾 Back Office

✔ STR Permit
✔ Tax Registration
✔ Insurance Policy
✔ CPA or Bookkeeping Software

📈 Performance

✔ Pricing Strategy
✔ Orphan Night Fills
✔ Review Monitoring
✔ Monthly P&L Reports

🏁 Final Thoughts: Treat It Like a Business

Running a short-term rental isn’t passive — but with the right systems, it can become predictable and scalable.

Use this checklist to build a foundation that’s clean, guest-ready, legally compliant, and built for growth.

Remember: You don’t need to do it all alone. Great tools and even better people can help you grow faster — and with fewer headaches.