LONG stay request. How to deal with

Hi all… I just received the first inquiry for a stay since early March (all pandemic related issues)!

The traveler wants to book close to three months this winter, the most busy time for my area.

The long term/squatter issue is understood and am thinking to suggest they make an initial reservation of 21 days (my max stay) and additional reservations to fill out their desired stay while accommodating the 21 day max stay.

It’s not clear how this would play out regarding as to when they would make the next reservation, the listing would be available to others interested parties, etc.

Any input, suggestions? FWIW, this a VRBO inquiry.

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Why would you want to do that in your peak season? Isn’t that why you have a max stay?

I would say no.


I’ve no idea where you’re located, but it’s generally accepted that in many jurisdictions the actual OTA reservations don’t mean much, it’s the physical presence of the guest in the property that determines the timescale in respect of being classed as a tenant, or an OTA guest.

I know getting a long term booking can take the pressure off, especially when it’s uncertain what future bookings will be like, but if you’re confident it’ll be busy then if it was me, I’d be inclined to take a chance on the season :grinning:

Incidentally, when we reopened we received several requests for long term reservations via VRBO, and all of them turned out to be either scams or sufficiently dodgy looking that we just declined them all.



In my off season 30-90 rentals are my bread & butter. I’m on Airbnb & although listed on VRBO have gotten few VRBO bookings so I’m not familiar with their processes.

My area considers rentals greater than 28 days as long term so in addition to the booking through Airbnb I ask them to sign a long term lease agreement.

The lease agreement gives additional them protection such as a 7 day inspection & opportunity to vacate if the rental is unacceptable (required by state law). Plus provides me with the tools for defining tenant rules/expectations & eviction process if necessary.

A realtor friend who has rental property shared a copy of the state realty commission approved lease.

DocuSign gives up up to 3 uses FREE. My guests create & account & e-sign. Easy peasy.

I have done a peak season LTR for a little less than my expected STRs because dealing with one rental is much less time consuming and less wear on the condo.

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JUST SAY NO!! mmmmmmm


Annet3176, I’m not certain about this, but someone else will probably tell us if I’m wrong. I don’t believe Airbnb allows you to have a guest sign an extra contract. If you’re going to accept bookings that are longer than 28 days, you should do so directly, without Airbnb involved.

From Airbnb help

Asking guests to sign a rental agreement

If you rent your home or apartment for monthly stays, consider whether you want guests to sign a rental agreement. If so, you should make these requirements clear in your House Rules before finalizing a booking. Laws governing these subjects vary widely depending on where you live, so be sure to contact a landlord-tenant attorney familiar with your local laws and regulations.


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Sometimes a prospective guest will try to impress you with an extended stay, figuring that it will save you a lot of work, and therefore it would be more attractive.

The laws in your jurisdiction are your first consideration. If there’s a problem with a plus 30 day reservation, obviously you can’t risk it.

My next question is why they are coming. Could be an IT nomad, or someone attending a school, or a coop situation. All plausible.
Next - what is the degree of their commitment? If they are paying up front, that’s good. Month to month is too much risk.

Other hosts may disagree, but guests putting a lot of money down up front tend to be less troublesome. However, they almost certainly will ask for extras.

Just had one. Great guest. Good money. Good rental.

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I’ve had both long term and short term over the years and now I’d never go back to long term.

You’ve set a minimum for a reason and if you go back on it for this person, they have you at a disadvantage - he/she hasn’t even stayed with you yet but you’ve already demonstrated to them that you don’t care about your rules. So why should they? That’s a really bad start.

Also ask yourself why they are using an advertising platform that usually deals mainly with STR. If they went through traditional LTR channels, they’d need to pass credit checks, background checks and so on. Just a thought but are they trying to avoid this?


I’m in Hawaii and the pandemic continues to strangle tourism. Even as we approach the holidays, the state is seeing approx 20% of the travelers we saw last year, same time period. So yes, I’m very interested in filling that bed.

I’m looking into the legal aspect. Thanks for the input.

Thanks for sharing how you handle it. I may need to find that long term lease form we used in the past.

They state that they are retired healthcare and a regular visitor to the islands.

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Again, other hosts may not agree with me. But retired means they are probably hanging out most of the time. It means that you are accommodating seniors for an extended period.

As pointed out, they are pushing your envelope in terms of booking duration. People give samples of their behavior.

The best advice I was ever given was ‘when in doubt, don’t’.

My personal experience and ‘how it works here’ is long term rentals are not leased to people who are not on island. People in that position arrive with a vacay rental reservation and scramble to find a long term rental before their vacay rental runs out. Been there, dealt with it.

Add to that the extreme shortage of long term rentals and it makes sense.

I feel it is a rare for people to fly to Hawaii and spend their time sitting in an apartment. In my experience, they come to be outside and enjoy what the islands offer. Guests rarely are at my place during daylight hours.

My take is that she is a snowbird who wants to spend this winter on Maui.

Thanks for the input!

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In normal times, yes. I live in a touristy beach town in Mexico and my guests have always been out and about most of their day as well.

But now with COVID, more guests are booking long-term stays because they just want to get out from their own 4 walls they’ve been cooped up in. If where they are from is cold, even more reason for them to want to go somewhere warm.

But unlike your past guests, many of these guests aren’t coming on vacation. They may be working remotely and be online many hours of the day. And with a lot of indoor dining closed down, or simply being cautious about being out much in public, they are cooking at home. So even though they will likely still be enjoying the beach and outdoor activities in a warm place, they will tend to be spending more time in the accommodation.

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Are you getting future bookings? Surely, those would conflict with a current guest’s need to stay longer.

Have you actually spoken to your guest about their plans and housing needs?

It’s easier said than done, but you need to decide if you’re a going to be a landlord and list long-term listings, or a STR host with short-term stays, and stick to your convictions. There may local accommodation and housing laws that might help you decide.

If you’re unsure, I would keep all their bookings and communication through Airbnb, and don’t offer deep discounts on long term stays. Price alone might be a deterrent.

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Another piece of good advice I was given by an attorney (I had been subpoenaed to give testimony) “if you feel like you’re talking too much or have said too much, you probably have. Just stop talking”. There are times I wished I had taken that advice more


My Tech nomads just left. They did exactly as you described.

Wonderful guests except for declining bug treatment (then agreed to pay for retreatmemt. Bug guy agreed to come back no additional charge when working next door!).

They left my home in great shape.


Hard pass.

Unless you need the $ to survive- why open yourself up to issues during the pandemic. If this person decides not to leave it will be hell getting them out. Expect very forgiving eviction short term law when biden gets sworn in to help fight the pandemic. May take 6 months to get someone out.

To wrap this up… the guest ended up taking my place for 15 nights, most of her stay is booked at a another place or two I gather*.

Why only 15 nights? She stated that she prefers ‘her own four walls’, IOW a stand alone structure. My suite is a self-contained, separate entrance and ‘everything else’ portion of the ground floor of my two story, but she had concerns.

*She asked about my place’s availability for the months of February and June, so her concern of an attached stay is now a non-issue.

She was as she self-described, a retired O.R. nurse who visits the islands for 5-6 months a year.

An ideal guest and as with all my past guests, she spent only the dark hours in the suite and the rest of the time out and about.

I can understand why a guest who likes her privacy might have concerns about a place like that until she experienced it for herself. There are some on-site hosts who are overly-friendly, would try to make conversation or “check in”, or just pop by to drop something off when it wasn’t welcomed. I remember reading a post once where the hosts had entered the guest cabin on their property when the guests were out one day to decorate it for Halloween. The hosts thought they were doing something fun that would be appreciated, but the guests were, of course, take aback and considered it an invasion of privacy. Not all hosts have appropriate notions of acceptable boundaries.