How do I start a short term rental business? A down-to-earth guide for new rental entrepreneurs

Ever tried juggling bookings, messages, cleaning schedules, and tax compliance all at once? It’s like playing Tetris—but blindfolded, with one hand, during a storm.

Starting a short term rental business can feel just like that—chaotic, exciting, and a little overwhelming. Whether you’re eyeing your first property or looking to expand from one cabin to a full-blown fleet of rentals, this guide is here to walk with you. Not lecture. Not pitch. Just practical help.

Let’s break it down.

Step 1: Define your short term rental business model

Are you renting out a single apartment downtown or managing a portfolio of vacation homes? Your model shapes everything else—from legal structure to software selection.

Common models include:

• Vacation rentals (Airbnb-style homes, cabins, apartments) 
• Equipment rentals (think cameras, paddle boards, party supplies) 
• Mobile spaces (trailers, vans, motorhomes) 
• Commercial units (office or retail spaces on flexible leases) 

For new rental services, check out this page on rental start-ups.

Step 2: Research legal and zoning requirements

This one’s not fun—but it’s non-negotiable.

Some cities have strict zoning laws. Others require permits, business licenses, or specific insurance. And if you’re renting out physical property, make sure you comply with short term occupancy limits, tax obligations, and safety codes.

Hot tip: Always register your business legally. A simple LLC can protect your assets down the road.

Step 3: Get your property or rental assets ready

Here’s where things get hands-on.

Whether it’s a furnished loft or a fleet of paddle boards, your inventory needs to shine. Think cleanliness, durability, aesthetics, and easy access. For equipment or gear-based rentals, inspect and log each item.

To manage your gear like a pro, try inventory rental management tools to track check-ins, damage, and availability.

Step 4: Set up a booking and payment system

This is where many small businesses stumble. Why? Because managing bookings manually—via DMs or spreadsheets—gets messy, fast.

Instead, get a rental booking software that handles:

• Online availability calendars 
• Instant or request-based bookings 
• Secure payments 
• Cancellations and rescheduling 
• Confirmation emails 

Tools like Sharefox’s online booking system are built for this—and scale with your business.

Step 5: List on multiple platforms (but own your traffic too)

Sure, Airbnb and VRBO bring traffic—but they also take commission and control your brand.

List on the big platforms, but also build your own online rental store using website booking systems. You’ll capture more revenue, own the customer journey, and appear more professional.

You can even integrate self-service rentals if you want to go fully contactless.

Step 6: Market your short term rental business

Marketing doesn’t have to be a beast.

Here are a few grassroots tactics that work:

• Google Business Profile for local search visibility 
• Instagram and TikTok for aesthetics and story-based content 
• Referral programs to reward happy guests 
• SEO-optimized content (like this article!) for long-term growth 

Need help designing your rental website? This rental website builder can help you go live in days, not months.

Step 7: Automate the boring stuff

Automation is your new best friend.

From customer emails to recurring payments and inventory syncs—automate wherever you can. This saves time, cuts down human error, and keeps your operations lean.

Explore subscription rental software if you plan to offer recurring packages (e.g., camera gear every month, or a monthly coworking desk).

Step 8: Measure, tweak, and scale

Once you’re live, it’s time to:

• Track your booking data 
• Understand your most profitable items or dates 
• Review guest feedback 
• A/B test your listing descriptions and pricing 

The businesses that grow aren’t always the ones with the best properties—but the ones that listen, adapt, and improve quickly.

The short term rental journey: From side hustle to serious business

Let’s be real—most short term rental businesses don’t start with a five-year plan.

They start with a feeling.

Maybe it’s the empty basement you never use. Maybe it’s the extra camera gear lying around after your wedding photography side gig. Or maybe—like Mads, one of our early Sharefox users—it started with a kayak.

Storytime: How a kayak rental turned into a thriving outdoor gear brand

Mads lived near a lake outside Oslo. One summer, a few neighbors asked to borrow his kayak. He agreed—then bought a second one. And a third.

By the end of the season, he had eight kayaks… and a spreadsheet that looked like a crime scene. Bookings, pick-up times, payment reminders—all over the place.

“I was texting people at midnight to remind them about life jackets,” he told us. “It wasn’t a business—it was chaos.”

Fast forward one year, and Mads runs a branded outdoor rental store with kayaks, paddle boards, and tents. His customers book online. Payments are handled automatically. Gear is tracked using rental inventory software.

He’s not alone.

Turning chaos into control: What growing rentals have in common

Here’s the truth most don’t talk about: the jump from side hustle to business happens when you get control.

Not more bookings.
Not more ads.
More clarity.

So, what helped Mads (and hundreds of others) grow?

1. A centralized booking system

No more juggling texts, Google Sheets, and phone calls.

Instead, Mads set up a booking system that shows real-time availability and lets customers self-book and pay online.

This freed him from admin tasks—and gave him weekends back.

2. Digital storefront = more trust

When people can browse your gear, read policies, and book in three clicks, they trust you more.

Your digital storefront (aka rental website) doesn’t just attract bookings. It builds credibility—especially for first-time customers.

3. Inventory tracking = fewer losses

Rentals are physical. Stuff breaks. Stuff gets lost.

A simple inventory management system tracks each asset—when it went out, who has it, and when it’s due back.

It’s like a library system, but for your business.

Scaling your short term rental: The playbook

Once your foundation is strong, it’s time to scale. Here’s what that looks like.

Build repeatable processes

• Use templates for messages, contracts, cleaning checklists 
• Create standard operating procedures (SOPs) 
• Use subscription models for recurring customers 

Expand your inventory—but carefully

Only add items that are:

– In demand
– Easy to maintain
– Profitable after 5–6 rentals

Pro tip: Use the jet ski rental calculator to model profitability. It works for other gear too.

Partner with locals

Mads didn’t grow alone. He teamed up with a local café for pick-ups and returns—adding value on both sides.

Think about your ecosystem: cafés, gyms, events, even real estate agents.

What Reddit taught us about starting rentals

We browsed through this excellent Reddit thread on short term rentals, and here’s what stood out:

“Start simple—get your first process right before thinking scale.”
“Expect cancellations, guest no-shows, and gear damage—it’s part of the game.”
“Once I automated payments and messages, my business doubled. I stopped being the bottleneck.”

Redditors are your peers. And they’re right: The tools and tactics don’t matter unless you step out of the weeds.

How Sharefox fits into your rental journey

We built Sharefox with folks like Mads in mind.

You shouldn’t need a developer, a marketing team, and an accountant just to run your business. You need:

• A calendar that syncs with bookings 
• An online booking tool that does the hard stuff for you 
• An inventory system that prevents losses 
• A checkout flow that builds trust 

And all of it, in one place.

Parting advice: You don’t need to go big. You just need to go smart.

If you’re sitting on that kayak, that apartment, that trailer—you don’t have to “build an empire.”

Start with one item.

One customer.

One weekend.

Then build processes. Test pricing. Automate the mess. And if you want help along the way? Book a demo with Sharefox. We’re rental people, too.

And we’re here to help you grow.