r/ShortTermRentals

Hey everyone,

I’m a property manager operating a small but growing business, and keeping our calendars aligned across different booking platforms is starting to turn into a daily operational nightmare.

I’m early in my research (currently running a trial with Lodgify), but I’d really appreciate hearing real-world experiences from anyone running similar operations.

A quick breakdown of our setup and what we need:

a.) We currently manage 7 short-term properties across multiple listing sites, so having a reliable system that keeps availability calendars synchronized in real time is our top requirement.

b.) We don't own all of these homes, so having a solid, dedicated owner portal where property owners can log in, view performance reports, and check availability is essential.

c.) We also handle all our turnover and maintenance in-house, so any software with built-in task assignment, cleaning schedules, or work order tracking features would be a huge plus.

A few peers suggested taking a look at platforms like Guesty, Hospitable, or Hostfully, but I want to see what people here are using for a growing setup like ours.

What software has worked best for you, and how has the customer support and reliability been? Thanks!

It seems like everyday I read within a post here that people are choosing hotels more and more over STR's. Yeah, well that's not true. A simple AI search shows that STR demand holds steady and in some cases gains ground.

I thought about this yesterday as I had possibly the worst sleep of my life at a "resort". I swear this place was an expensive crap motel masquerading itself as a resort.

1. Rude front desk staff
2. Screaming kids everywhere
3. Dirty rooms
4. Banging on the walls from the unit next door
5. The worst pillows and bed ever!!!...sunken in, it swallowed me whole.

All this I mentioned at the front desk while checking out. The clerk robotically said she would pass my concerns on to management. Sure she will. 🤣

Today I had to spend yet more money on a massage to get rid of the body aches caused by that bed. During that massage I was thinking I should have just staycationed in my own STR.

I submitted new photos to my co-host to replace some photos due to furniture changes. How long would a professional amount of time be for them to update them? From what I understand, new photos can be seen within 30 minutes and at the latest 24 hrs.

Hello all, settling soon on a property in a beach town that only really rents well in the summer. I want to use it with my family a fair amount in the shoulder seasons but am afraid I will go over the 14 personal use days maximum. I know you can go for “maintenance” and have those days not count as personal, but just wondering how do you report personal use days when you file for taxes, how does the irs check on this stipulation. TIA.

I looked into STR for tax deferral advantages and got excited. Then I learned it has to be paid back when you sell the property. Sure you can 1031, but you still aren’t becoming liquid…so it appears that you essentially will be building wealth through equity in real estate that you can’t ever sell. Few properties appear to cash flow enough to make it worth it & getting a promotion at work is more sizable. Break even gets you the appreciation, but you need a good 15 years into a 30 year mortgage to have a sizable return worth the amount of work (Pigeon Forge properties are primo STRs and seems to be appreciating at only 4-4.5% per year on average)

So my question for those who have short term rentals…

What is your personal end game with your STRs?

Wife and I both work full time and we are closing on our first rental property. I talked with my cpa today and she basically said that there’s no way that I’d be able to justify utilizing the STR loophole given our current situation.

She threw out 700 and 1000 hours as target minimums. She also does a fair amount of IRS representation, so I do trust her judgement. Im ok with being slightly aggressive from a tax planning standpoint, but there’s a difference between aggressive and foolish.

Figured I’d ask out of curiosity though if anyone has done this with just one property. Thanks!

I used to use the smart lock feature, but I hated the long generic message it sent direct to the guest before I ever had a chance to communicate. I’d like to test the waters again, but not unless the experience has changed.

How does it work these days?

I’m a landlord and I have a potential tenant that wants to use my property as a STR. I’ve done some vetting of the tenant and I’m comfortable moving forward with them.

The last problem I’m coming across is our insurance does not like the idea and said they would not insure for that scenario.

Does anyone have experience getting insurance as the property owner in an arbitrage situation? What did you end up doing?

I've seen this question come up a lot in the Rocky Point / Puerto Peñasco Facebook groups, especially with people booking condos owner-direct:

How do you actually verify that the person you're talking to is the real owner or authorized to rent the property?

I'm a Rocky Point condo owner myself, and this has been one of the biggest challenges we've had with owner-direct rentals. Airbnb and Vrbo are expensive, so booking directly can save both the owner and renter a lot of money. But I completely understand why someone is nervous about sending $1,000-$2,000+ to a person they met through Facebook.

The problem is that most of the things we use to establish trust aren't really verification.

The condo can be real. The photos can be real. The owner's name can be real. Someone can provide a phone number, send a voice message, or even copy information from a legitimate listing.

None of that necessarily proves the Facebook profile, phone number, email, website, or payment information you're dealing with actually belongs to someone authorized to rent that condo.

I couldn't find a simple way for renters to independently check that, so I started building one.

It's called CasaRecord.

A Rocky Point vacation rental owner can verify their identity and relationship to the property, then register the actual contact methods they use for rentals.

A traveler can then go directly to CasaRecord and check the contact information they already have. If it matches, CasaRecord shows the verified property associated with it.

The important part is that you don't have to ask the person you're talking to for a special verification link or trust a screenshot or badge they send you. You can independently check the contact yourself.

CasaRecord is still in beta, and I'm currently looking for Rocky Point / Puerto Peñasco property owners and travelers willing to test it and tell me where it needs improvement.

It's free to use: CasaRecord.com

I'd also genuinely like to hear what everyone else currently does to verify an owner-direct Rocky Point rental before sending a deposit. There may be methods I'm overlooking.

We do not have occupancy regulations in our town, so I can list either 12 or 14.

My bedrooms are:
BR1 King (2 guest)
BR2 King (2 guest)
BR3 2 Queen (4 guest)
BR4 2 full-over-full bunk bed (4 or 6 guest)

Would you do 4 guest or 6 guest for BR4?

My wife and I are considering buying a property and make STR for tax incentives and investment. This particular property would be 5BR in Pigeon Forge, and we live 4 hours away.

What is your experience with being able to manage the property when you are not local? We would self manage as much as possible, but not opposed to outsourcing some management as long as we qualify for “self managed” for tax incentive.

Hi all. I own a small Airbnb management and cleaning company. Eight apartments in the portfolio so far five with individual owners who live abroad, three with a newly formed company. I handle everything end to end, and all of them have stayed with me.
Looking to grow now.
If you own a property and are considering short-term rental, or know someone who is, I'd appreciate an introduction. Same if you're with a holiday home company open to working together.
Happy to answer anything in the comments or by DM.

I have a 3 bedrooms, 2 spa like bathrooms, top of the line laundry room in Sunland, CA how profitable will be to rent it to traveling professionals? Or it is better to just do a regular 1 year lease. The initial investment will be around $16k. The house has a nice front and back yard with a separated entrance to the ADU. 1,400 sq f. Quiet neighborhood.

I am considering purchasing an investment property via a ltd co. Have looked at some new builds near a big tourist attraction in the south-east of England (not London).

It’s currently unclear, but the sales rep from the developer side said that there is a restriction against holiday lets. It’s not from the council according to research so maybe something that will be in the lease or planning permissions.

They did mention that another developer on their site had the restrictions lifted. There also appears to be properties on their specific development which are actively advertised on platforms with guest reviews in recent weeks.

Does anyone here have experience of this situation? Is it possible to work around such a restriction? How feasible is it that it can be enforced? Would appreciate any knowledge and insights.

I own a short-term rental property management company called Wilder Stays, and I’m trying to figure out the best way to grow our owner/client side of the business throughout Central and Northern Wisconsin.

We currently manage a growing portfolio of cabins, cottages, homes, and other vacation rentals across the Northwoods. We handle things like guest communication, pricing, booking management, cleaning and maintenance coordination, listing optimization, and the day-to-day operations for owners who don’t want to manage everything themselves.

Most of our growth so far has come organically through relationships and referrals, but I’d like to become more intentional about reaching owners who already have an Airbnb/VRBO or are thinking about turning a property into a short-term rental.

For anyone who owns vacation rentals or works in the industry:

What would actually make you consider switching to or hiring a property manager?

Would you respond better to direct outreach, referrals from realtors/cleaners/contractors, local Facebook groups, mailers, networking, or something else?

And for owners who currently self-manage, what is the biggest thing that would have to happen before you’d consider handing management off to someone?

I’m especially interested in what works in smaller markets like Minocqua, Wausau, Rhinelander, Tomahawk, Crandon, Eagle River, and the surrounding Northwoods rather than major vacation markets.

Not trying to turn this into a sales post. I’m genuinely trying to understand how property owners prefer to be approached and what actually builds trust with a local management company! Thanks in advance!

Hey gang, Is there a dedicated website that has STR's listed for sale? Looking to purchase an existing STR in Florida but having a hard time finding legit existing STR properties that are currently up and running with excising income. Any help or pointers to find listings would be appreciated.

Hi, received a booking that the bookers story is not really adding up so I'm starting to think it might be a set up for a party. I live just down the street from the property so I can keep a close eye on it.

But I'm curious as STR Hosts, what are my rights? What can we do if I suspect underage drinking in a property?

Here in Texas it's strictly forbidden if you're under 21.

Thanks! J