10 Proven Steps to Manage Short-Term Rentals Like a Pro

Successfully managing short-term rentals starts with a solid plan. If you’re new to the game, deciding whether to self-manage or hire a property manager is crucial. 

Self-management offers complete control but demands time and effort to handle guest communication, revenue management, cleaning, and maintenance. 

If you’re short on time, or just don't feel like taking on the headaches - hiring a property manager can ease the burden while ensuring smooth operations.

If you’re ready to step into the world of short-term rentals or improve the performance of your current property, this guide will walk you through 10 actionable steps to build a thriving rental business. Whether you prefer to manage everything yourself or delegate tasks to a professional, these tips will help you navigate the challenges of rental management with confidence and ease.

1. Choose Your Management Style: Decide between self-managing or hiring a property manager. For self-managers, create a detailed checklist of daily, weekly, and monthly tasks.

2. Get Licensed: Research and obtain all necessary business and short-term rental permits. New short-term rental permits are not allowed in every location, so be sure to confirm they are available in your area, in order to avoid steep fines and penalties.

3. Protect Your Assets: Set up an LLC and secure appropriate insurance. Not every insurance policy protects property owners who rent their home out for under 30 day stays, even policies that protect investment properties. It's imperative to confirm that vacation rentals or short-term rentals are covered under your policy.
   There are many that you can choose from, but three that we recommend are Proper Insurance: https://www.proper.insure/, Openly: https://openly.com/, and Kin Insurance: https://www.kin.com/.

4. Design Your Property: Decide whether you'd like to self-design, or hire a designer that specializes in short-term rentals in order to really maximize your booking revenue potential.
   Tip: Sienna Stays offers professional design services tailored to vacation rentals, and we love helping people get started!

5. Stock Up on Amenities: First focus on essentials and add then thoughtful extras, like local guidebooks or complimentary snacks. Investigate what other rentals in your area offer, and make sure you are offering the same when possible. For example, if you have a home in the Smoky Mountains and all vacation rentals nearby have a hot tub, you will want to add a hot tub to your property in order to maximize revenue.
   Bonus: Stay tuned for future blog posts, as we will share our list of essential amenities that come standard in all of our properties.

6. Create a Stunning Listing: Use professional photos and write detailed descriptions that highlight key features.

7. Prioritize Reviews: Ask satisfied guests to leave feedback and address any negative comments promptly.

8. Maintain the Property: Regularly inspect for repairs and ensure everything is guest-ready.

9. Budget Wisely: Track all income and expenses using accounting software or a dedicated spreadsheet.

10. Stay Tax Ready: Use a dedicated bank account for rental finances and consult a CPA for deductions.

Now that you’ve got a solid overview of the steps involved in managing a successful short-term rental, let’s break each one down into actionable items.

The following checklist provides a practical guide to help you stay organized, ensure nothing falls through the cracks, and streamline your rental operations.

Choose Your Management Style

• Decide between self-management or hiring a property manager.
  For self-managers:

• Create a daily task list (guest communication, cleaning coordination).

• Outline weekly tasks (supply restocking, property inspections).

• Schedule monthly tasks (marketing updates, maintenance checks).

Get Licensed

• Research local and state requirements for short-term rental permits.

• Obtain a business license.

• Secure a short-term rental permit.

• Check if you need a certificate of occupancy or sales tax registration.

Protect Your Assets

• Establish an LLC for liability protection.

• Obtain rental property insurance and liability coverage.

• Draft clear renter guidelines and house rules.

• Invest in security measures (locks, cameras, or smart systems).

Design Your Property

• Decide if you will design your property yourself, or hire a professional designer

• Determine your design budget. A good rough estimate is to budget around $3-5k per bedroom, possibly more if your home has a lot of outdoor living spaces you plan to furnish.

• Create a list of the furnishings you need to purchase for each separate space in your home. Stay tuned for a future blog post where we will share links to the Essentials we recommend every vacation rental has.

• If your budget allows, plan to add accent walls, wallpaper, or other special elements to really make your listing pop!

Stock Up on Amenities

• Research your "competition" to ensure that the amenities you offer meet or exceed what guests expect in your area. Stay tuned for our "Enemy Method" spreadsheet we use to compare our properties to the competition.

• Provide essentials: linens, towels, toiletries, kitchen supplies.

• Add extras like local guidebooks, snacks, or wine as a welcome gift. Consult with an attorney to understand the implications if you do provide wine or other spirits to guests upon arrival. Our philosophy at Sienna Stays is to simplify and mitigate risk whenever possible, so we no longer offer alcoholic beverages as a welcome gift.

• Tailor amenities to your audience (e.g., kids’ toys for families, workspaces for business travelers).

Create a Stunning Listing

• Hire a professional photographer for high-quality photos.

• Write a detailed, SEO-optimized property description.

• Highlight unique features and nearby attractions.

• Update your listing seasonally or after upgrades.

• Regularly update pricing and consider adding a Dynamic Pricing software like PriceLabs: https://hello.pricelabs.co/

Prioritize Reviews

• Communicate promptly and professionally with guests.

• Ensure the property is as advertised (clean and well-stocked).

• Surprise guests with thoughtful touches (welcome notes, small gifts).

• Follow up after stays to request reviews.

Maintain the Property

• Schedule regular inspections to identify and fix issues.

• Address minor repairs before they escalate.

• Keep HVAC systems and appliances in good working order.

• Partner with reliable cleaners and handymen. We highly recommend having 3 of each vendor, just in case one is unable to perform the job duties when needed. The more you plan for the unexpected, the more prepared you'll be.

Budget Wisely

• Track income and expenses using accounting software.

• Open a separate bank account for rental transactions.

• Set aside funds for unexpected repairs and upgrades.

• Monitor property performance with financial reports.

Stay Tax Ready

• Open a dedicated bank account for rental finances.

• Keep receipts and records of all income and expenses.

• Use accounting software to generate accurate financial reports.

• Consult a CPA to understand deductible expenses and ensure compliance.

This checklist can serve as a quick reference for managing your short-term rental and staying on top of daily, weekly, and more long-term tasks as you grow your business!

Interested to see how your listing can be improved? Feel free to reach out to us for a complimentary listing audit!

***Legal Disclaimer: None of this information is meant to be taken as legal advice. Regulations and policies vary by city, state, and county. We advise you to consult an attorney to ensure compliance to your local guidelines.***