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Turning a long-term rental into a short-term rental can feel like a big leap, especially if you have only ever dealt with year-long leases and predictable monthly income. With short-term rentals, the upside is higher earning potential and more control over your property, but it also comes with new rules, new costs, and a different way of operating day to day. That is why it helps to understand what the transition actually involves before you jump in.
Below, we will walk through what it takes to move from a long-term rental to a short-term rental in a practical, step-by-step way.
Quick reality check: Is your property a good STR candidate?
Before you start buying furniture or creating a listing, it is worth stepping back and asking one simple question: does this property actually make sense as a short-term rental? Not every long-term rental will perform well with nightly stays, even in popular areas.
Start by looking at local demand. Properties near hospitals, universities, and major employers often attract traveling nurses, visiting professors, and business travelers. Seasonal demand also matters. Beach towns, ski areas, and festival-heavy cities may earn more in peak months but slow down during the off season. Drive-to attractions like national parks, lakes, and family destinations can also support steady weekend and holiday bookings.
Next, weigh the tradeoff. Short-term rentals can generate higher income, but they also bring higher turnover and more hands-on costs. Cleaning between guests, replacing worn items, and handling minor repairs happen far more often. If the numbers still work after factoring in that extra effort, your property is likely a strong STR candidate.
Rules First: Zoning, Permits, HOA Restrictions, and Local Taxes
Before you buy furniture or create a listing, make sure short-term rentals are actually allowed where your property is located. Cities and counties often have specific zoning rules that limit or regulate short-term rentals. These can include permit or registration requirements, caps on the number of guests, parking rules, and enforced quiet hours. Some areas also require safety inspections or a local contact person who can respond to issues quickly.
If your property is in an HOA or condo association, read the bylaws carefully. Many HOAs prohibit short-term rentals outright or impose minimum stay requirements that make Airbnb-style hosting impossible.
It is also important to remember that these rules vary by city and can change over time. Platforms like Airbnb now prompt hosts to complete registration steps where required, but you should never rely on the platform alone for compliance.
One thing you should not skip is local lodging or occupancy taxes. Many cities require hosts to collect and remit these taxes, and missing them can lead to fines or shutdowns.
Exit Your Long-Term Lease The Right Way Without Drama
Before you think about furnishings or listings, take care of the lease you already have in place. Start by reviewing the lease end date, any renewal clauses, and the required notice period. Many leases require 30 to 60 days written notice, and missing that window can automatically extend the agreement. Scheduling a move-out inspection early also helps you understand what repairs or cleaning will be expected before the tenant leaves.
Next, be clear about repair responsibilities and the security deposit. Normal wear and tear is usually on the owner, while tenant-caused damage can be deducted from the deposit. Document the condition of the unit with photos and written notes so there are no surprises or disputes later.
If you are considering converting the property before the lease ends, move carefully. Your main options usually include:
- Waiting until the lease naturally expires
- Agreeing to a mutual early termination in writing
- Offering cash-for-keys to help the tenant relocate
Whatever path you choose, keeping things fair, legal, and respectful protects you from headaches and reputational risk down the road.
Re-Run Your Numbers: STR Income, Startup Costs, and Ongoing Expenses
Before you commit to the switch, you need to look at your numbers with fresh eyes. Short-term rentals can earn more than long-term rentals, but only if the math actually works for your property and market. This step is about getting realistic, not optimistic.
Start with your one-time setup costs. Even if the home is already in good shape, most long-term rentals need some investment before they are guest-ready. Common startup expenses include:
- Minor repairs and touch-ups
- Furniture and decor
- Extra linens and towels
- A fully stocked kitchen kit
- Smart locks, WiFi upgrades, or noise monitors
- Professional photography for your listing
Next, factor in ongoing expenses. These tend to be higher and more frequent than with a long-term tenant. Expect regular cleaning between stays, restocking basics like paper goods and toiletries, higher utility bills, and more wear and tear that leads to maintenance happening more often.
Finally, decide your breakeven occupancy target. Add up your total monthly costs, then divide that number by your average nightly rate. The result tells you how many nights per month you need booked just to cover expenses. If that number feels unrealistic for your market, it is a sign to pause and reassess before moving forward.
Upgrade the Property for Guest-Ready Durability
A long-term rental only needs to survive one tenant at a time. A short-term rental has to hold up to dozens of different guests every year. That means durability matters just as much as style. Before you start taking bookings, it is worth spending time “hotel-proofing” the space so normal wear and tear does not turn into constant repair calls.
Focus first on the basics that get used and touched every day. Fresh paint in a neutral, washable finish makes touch-ups easier between guests. Good lighting helps the space feel clean and safe, and it reduces complaints about dark hallways or bedrooms. Smart locks or keypad entry systems cut down on lost keys and make check-ins smoother. Whenever possible, choose easy-clean surfaces for floors, counters, and furniture so turnovers stay fast and predictable.
- Touch up walls with durable, washable paint
- Upgrade lighting in bedrooms, bathrooms, and entry areas
- Install smart locks or keypads for secure self check-in
- Choose hard flooring or low-pile rugs that clean easily
- Keep backup supplies like bulbs, batteries, linens, and towels on hand
It is also smart to create a small owner’s closet or locked supply zone. This gives you a place to store extra linens, cleaning products, and replacement items without leaving everything accessible to guests. A simple locked cabinet or closet can save time, protect your inventory, and make turnovers much more efficient.
Safety and Compliance Essentials (Non-Negotiables)
Before you ever accept your first booking, safety and compliance need to be locked in. This is not just about protecting guests. It also protects you from liability issues, bad reviews, and potential problems with local regulators.
Start with the basics that most cities and platforms expect as a minimum standard. Your property should have working smoke detectors and carbon monoxide detectors in all required areas, along with a visible fire extinguisher and a stocked first-aid kit. Just as important is clear emergency information. Guests should know who to call, where exits are located, and what to do in case of a fire, power outage, or medical issue. Posting this inside the unit and including it in your digital guide helps prevent confusion.
Secure entry is another must. A keypad or smart lock allows for smooth self check-in and eliminates the risk of lost keys. Pair this with simple, step by step check-in instructions so guests can arrive confidently without needing to contact you.
Furnish and Stock Like a Real Stay, Not a Staged Photo
A property can photograph beautifully and still disappoint guests if it is missing everyday essentials. Think about how someone actually lives in a space for a few days, not how it looks in a listing photo.
Start with the basics in every room. Bedrooms should have comfortable beds, quality mattresses, and at least two full sets of clean linens per bed. Bathrooms need enough towels for the maximum guest count, plus backups, along with simple items like toilet paper, hand soap, and shower essentials. In the kitchen, focus on functionality. Guests expect cookware, plates, glasses, utensils, a coffee setup, and a few pantry basics, not decorative pieces they are afraid to touch.
If you want to speed things up and avoid costly furnishing mistakes, Awning offers rental furnishing and design services built specifically for short-term rentals. Their team focuses on durability, guest comfort, and layouts that actually perform well for bookings, not just looks. It is a practical option if you want a professionally designed space without spending weeks sourcing furniture, decor, and essentials on your own.
Lastly, create a standard restock par list so nothing runs out between stays. This should include items like paper towels, trash bags, dish soap, coffee, and toiletries. Having a simple checklist makes turnovers faster and keeps the guest experience consistent.
Insurance Update: Don’t Assume Your Old Policy Covers STR
Don’t assume your existing landlord or homeowner insurance is enough. In most cases, it is not. Short-term rentals are viewed as a different risk category, mainly because you have frequent guest turnover, higher liability exposure, and more wear and tear on the property.
Standard landlord policies are designed for long-term tenants, not weekend guests, vacationers, or business travelers. Some insurers may even deny claims if they discover the property is being used as a short-term rental without the right coverage. This is why many owners work with agents who understand STRs or move to policies built specifically for short-term rentals.
When updating your coverage, you may need to consider:
- Higher liability limits to protect against guest injuries
- Damage protection for accidental guest-related damage
- An umbrella policy if you want extra protection beyond standard limits
If you want a simpler, STR-specific option, Awning offers insurance designed specifically for Airbnb and short-term rental hosts. Their coverage is built to match how STRs actually operate, not how traditional rentals work. You can explore your options and get a quote from Awning to make sure your property is properly protected before you launch.
Build Your Operating System: Cleaning, Turnover, and Guest Communication
Once your property is set up, your success will depend on how smoothly it runs between guests. Short-term rentals live and die by turnovers, so you want systems in place that work even when you are busy or unavailable.
Cleaning cadence and inspection checklist
Every turnover should follow the same routine, whether a guest stayed one night or seven. At a minimum, cleaning should happen after every checkout, with a quick inspection to catch small issues before they become bad reviews. Your checklist should include basics like linens, bathrooms, floors, trash removal, and restocking supplies, along with a final walk-through to check lights, locks, and appliances. Consistency matters more than speed here.
Self-check-in flow and messaging templates
Self-check-in is now the standard. A keypad or smart lock makes arrivals easier for guests and reduces coordination on your end. Pair that with pre-written messages for booking confirmation, check-in instructions, house reminders, and checkout steps. This saves time and keeps communication clear and professional.
DIY vs. co-host vs. property manager
If you live nearby and enjoy hands-on work, managing it yourself can make sense at first. As bookings increase or distance becomes an issue, a co-host or property manager can take over day-to-day tasks like cleaning coordination and guest messaging. Outsourcing usually makes sense once time becomes a bigger cost than money.
Create a High-Converting Listing (Photos, Description, and Amenities)
Once your place is ready, your listing is what turns browsers into booked guests. Start with professional photos if at all possible. Clear, well-lit images make a huge difference in how often your listing gets clicked and how trustworthy it feels. Many experienced hosts, including teams like Short Term Stay Pros, point to photos as one of the biggest factors in faster bookings and better reviews. Think of your photos as your first impression. They should show the full space, highlight unique features, and set accurate expectations.
Your description should be clear and easy to scan, not flowery or vague. Guests want to quickly understand whether your place fits their needs. Be specific about the details that matter most, including:
- Sleeping layout and bed sizes
- Parking availability and any restrictions
- Wi-Fi speed and reliability
- Dedicated workspace or work-friendly setup
- Pet policy and any related fees
- Stairs or accessibility considerations
When guests know exactly what they are booking, you attract better-fit stays and avoid problems later.
Pricing and Minimum Stays: Launch Strategy for Your First 30 to 60 Days
The first month or two of your short-term rental is less about maximizing profit and more about building momentum. At this stage, your main goal is to get bookings, collect positive reviews, and prove to both guests and booking platforms that your property is reliable and worth choosing.
A smart way to do this is to start with slightly lower, competitive pricing and a few tighter restrictions. This might mean setting a two or three night minimum stay instead of one night, or limiting availability while you learn how turnovers and guest communication really work. These early guardrails help reduce stress while you dial in your systems.
Pricing should not stay flat. Adjust rates for weekends, peak seasons, and local events like festivals, sports tournaments, or conferences that drive short-term demand. Your cleaning fee should reflect your actual cost and time, not act as a profit center. Guests are more forgiving of nightly rates than inflated cleaning fees, especially when reviews are still coming in.
Launch, Then Optimize (Simple Weekly Routine)
Once your listing is live and bookings start coming in, the real work begins. The goal in the first few weeks is not perfection. It is paying attention. Short-term rentals perform best when you treat them as a living system that improves over time.
Set aside a short check-in each week to review your core numbers. You do not need complicated spreadsheets to start. Focus on a few simple metrics that tell you how the property is actually performing:
- Occupancy rate and which days are staying empty
- Average daily rate and whether guests are booking at your target price
- Total revenue compared to your monthly goal
- Cleaning cost percentage to make sure turnovers are staying profitable
- Maintenance issues that keep popping up
- Review themes, both positive and negative
Use what guests tell you to refine your listing and house rules. If multiple guests mention confusing check-in instructions, unclear parking, or missing kitchen items, fix it right away. Small updates based on real feedback can quickly improve reviews, reduce problems, and increase bookings.
The Bottom Line
Transitioning a long-term rental into a short-term rental can be a smart move, but it works best when you approach it with a plan. From understanding local rules to setting up the property, pricing it correctly, and dialing in your operations, each step plays a role in long-term success.
The good news is that you do not have to get everything perfect on day one. Most successful short-term rentals improve over time by learning from real guest behavior and adjusting along the way.
If you want to skip the trial-and-error phase or scale faster with fewer headaches, Awning’s property management services can help. Awning handles everything from listing setup and pricing to guest communication and ongoing optimization, making the transition from long-term to short-term renting smoother and more profitable.
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