Managing Your Vacation Rental

Unexpected Issues with Longer-term bookings

Written by Elizabeth Weedon
4.7/5 - (10 votes)

Updated August 2023

Some owners would much prefer to have multiple-week renters over single-week ones. If you are one of them, what things should you consider before you commit to hosting a longer-term tenant? 

Why multiple-week stays are so attractive

Let’s start with the advantages to you as the homeownerIt’s great to have fewer turnovers, which are stressful and costly. There are also fewer bookings to process and fewer guests to cater to (sending information, checking in with them, answering questions, etc.)  And some would argue that there are fewer cleanings needed, although that’s not necessarily true (see below). 

Important issues to consider

Here are some other issues to be aware of when renting to long-term tenants:

  • Less money and Increased costs. To seal a long-term deal, homeowners often provide long-term guests with discounts. In addition, they make other concessions such as increasing their Internet capability, changing bed configurations, providing linens, etc.
  • Greater risks for homeowners. If any problems arise between you and your longer-term guest, there’s more at stake for both of you, financially and logistically.
    • If they demand money back, it could be devastating to you if it becomes necessary to do so.
    • If they cancel close to the time of their arrival, and you feel obligated to refund them even in part, you’re left scrambling to fill multiple weeks.
    • You might risk losing some valued repeat guests.
    • You lose the ability to access your home regularly in case of maintenance issues or problems of any kind.
  • Cleaning. Unless you insist that your house cleaner continue to provide weekly cleaning during a longer stay, it is nearly impossible to adequately clean the house within the few hours of a normal turnover. A deeper, more time-consuming cleaning is necessary, negating any savings on cleaning costs.
  • Increased wear and tear. Longer-term tenants tend to hunker down and spend significantly more time IN your home than those who are there on a one-week vacation. Spending more time in and around the home translates to more wear and tear in general. Instead of eating out, they cook at home on your stove and grill more than ever, requiring more deep cleaning. 
  • A more fastidious tenant. Whereas a weekly guest might roll with an issue they have in your home, someone staying for multiple weeks is much more apt to demand that everything be fixed or provided to their liking.
  • The exit strategy (or lack thereof). We have heard of a few instances in which a long-term renter refuses to leave, claiming they have no place to go. This is more likely to happen during the off season.
  • MA Lead Paint Disclosure laws apply. Owners of a home built before 1978 must comply with Lead Paint Laws if they are renting their home for more than 31 days.
  • MA Security Deposit Law. For tenancies of 90 days or more, the landlord is required to hold the tenant’s security deposit in a separate bank account in MA.
  • Fewer guest reviews. With fewer parties staying in your home over the season, you have fewer opportunities to receive valuable guest reviews.

Steps you can take to avoid problems

Greater scrutiny of prospective guests. Increase your screening process to find out more about your guests and to ensure that they are a really good fit in your home. Research them online through Google and social media. Absolutely be sure to have a phone or video conversation with them prior to committing.

Research the reason for the long-term rental request. If a long-term renter refuses to leave at the end of their lease, a judge might be more compassionate if it is determined that the tenant is using the residence as a primary home and “needs time” to find a new place to live. An eviction process could take months.

Meet with the prospective guests prior to booking. If at all possible, have them meet you at the home before you and they commit to the tenancy. Or meet virtually by Skype, Zoom, or FaceTime. This is the best way to avoid expectations that are not met.

Allow more time between guests for both cleaning and maintenance. You will undoubtedly need more time to check the home thoroughly and make any needed repairs or new provisioning.

Require regular cleanings. Insist that your longer-term guests allow, if not pay for, your cleaners to enter the home during their stay to keep it adequately cleaned. Otherwise, it’s too overwhelming for cleaners to do a deep cleaning after the departure of your long-term guests.

Charge a higher security deposit. Due to increased risks, it’s reasonable to also increase your security deposit.

Consult an attorney. Have a lawyer review or draft your lease agreement to ensure that you have adequate protection.  Legal counsel can also advise on current landlord-tenant laws.

About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for since 2008, I’ve been a loyal homeowner on the site since early 1998, just a few months after the website was launched by the Talmadges. I grew up summering on the Vineyard and managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation, which I credit with enabling me to hold onto the special property that has been in our family for nearly a century. An enthusiastic member of the WNAV Homeowner Support Team, I endeavor to keep my finger on the pulse of the Cape and Islands vacation rental industry so that I can provide homeowners advice about how to ensure their booking success with us. With owner Joan Talmadge, I am also responsible for editing and writing much of the text on our website, our monthly newsletters, and Homeowner Blog posts.

1 Comment

  • Since there are pros and cons involved in many rental decisions, I appreciate your well-grounded discussions. Thank you!