Simple, Compliant Bookkeeping for Short-Term Rental Managers with Under 10 Listings

Managing a small portfolio of short-term rental (STR) listings, between one and ten properties, can be overwhelming, especially when it comes to bookkeeping. If keeping track of owner payouts, taxes, and income feels confusing or stressful, you are not behind. You are right where most STR managers are in this stage of business, especially those of you doing this as a side hustle. Every minute you spend on the business is precious, and time spent tracking down receipts can be better spent elsewhere.

At this phase, you have real money moving, real owner relationships, and real responsibilities. Maybe you even have your first team member. But without formal systems, scale, or a large team, it is easy for bookkeeping to feel reactive or stressful.

In this post, we will walk through simple, compliant bookkeeping strategies for STR managers, so you can manage your listings efficiently, stay compliant, and set yourself up for growth.

Do You Really Need Trust Accounting as a Small STR Manager?

If you are collecting rental income on behalf of property owners, you need some form of trust accounting. This is not just a suggestion; it is a fiduciary responsibility. While laws on the books may be a little less defined compared to the LTR industry, that doesn’t make this any less important. In fact, with STR’s, the higher transaction volume makes it even more important. Given the timing differences in payouts between booking channels, trust accounting ensures that you properly manage owner funds until it is time to pay them.

At a minimum, your bookkeeping should track:

Owner payouts: How much each homeowner should receive net of expenses
Rental taxes owed: Ideally broken down by owner (and definitely by channel!)
Future bookings: Deposits collected for stays that have not occurred yet
Manager payouts: How much you earn

Even with just a few properties, proper tracking prevents confusion, misallocated funds, and potential legal or cash flow issues as your business grows.

Key takeaway: It is not about the software you use; it is about keeping funds separated, reserved, and paid consistently. Whether that is via Excel, multiple bank accounts, or STR-specific software, clarity is what matters most.

Minimum Bookkeeping Setup to Stay Compliant

Here is the bare-minimum bookkeeping setup for STR managers with under 10 listings:

Dedicated business bank account – No commingling with personal funds, keep owner funds in a separate trust account
Track all rental income – Ensure all bookings flow into the trust account
Owner payouts and taxes – Pay according to agreements and remit taxes correctly
Manager payouts – After everything else is accounted for, pay yourself

A simple check: at the end of the month, with all funds are accounted for, your trust account balance at the end of the month should go to zero (excluding future bookings) because every dollar has a clear purpose.

Remember: You need to track two things by owner: money coming in and money going out. Records should also make sense to someone else, not just you, so others can audit or step in if needed. You don’t intend to be stuck in the books forever, do you? Document now while it’s fresh, before you scale.

How to Set Yourself Up for Scaling Your STR Business

Scaling your STR business relies on clear, repeatable systems. Ask yourself:

Can I easily explain who gets what from a booking?
Is every owner commission calculated consistently?

For example, if a guest books a property for $500 per night, pays a $350 cleaning fee, and $100 for a pet, can you immediately explain how that money is split between owner, cleaning, taxes, and manager fees?

If the answer is yes, your foundation supports growth. If not, it is time to strengthen your systems before scaling. Clear bookkeeping now prevents errors, stress, and confusion later.

Are You Probably Doing Okay Right Now?

Many managers with 1- 10 listings are closer to compliant than they realize. If you have:

A separate business account
Owner funds kept separate from your business account
Clear payouts you can explain

…you are likely on the right track.

How Keystone Bookkeepers Can Help

If at any point you decide you do not want to tackle STR bookkeeping alone, Keystone Bookkeepers exists to help managers like you. We specialize in helping small property management businesses:

Set up compliant, scalable bookkeeping systems
Track owner payouts and rental income efficiently
Manage trust accounting and tax obligations

With Keystone, you can focus on growing your short-term rental business while we handle the bookkeeping foundation that keeps your business compliant and stress-free.

Start today by reaching out to learn how we can simplify your STR bookkeeping.