I’ll admit it: I’ve become a bit of a vacation rental junkie. As I write this article, I have two homes in two cities paid for, and a third — an annual, multi-week rental in my favorite town — booked.

This is a big admission coming from a girl who adores the “vacate” aspect of vacations; why would one EVER want to cook/make beds/not have room service as an option when one is on vacation? Turns out, there’s often more than one answer to that question.

This month, I’m taking my daughter to Chicago to tour four colleges in six days, and I want her to experience a real slice of city living — not the fantasy hotel version of it — should she decide on a college in the city. Also, I needed a rental property for my son’s upcoming college graduation. That was really more of an “oops!” though, because I totally forgot to make hotel reservations, and every hotel room in town was booked by December. So I jumped online to find a rental and was able to book one of the last available homes in town that could accommodate everyone, including my parents.

Ever since booking my first vacation rental online in 2007, I’ve changed my vacation mindset to include checking rental-by-owner websites as I peruse the offerings from more traditional hotel and resort websites. And (knock on wood) I’ve never had a problem with any aspect of booking through one of these sites. Unlike booking a hotel or resort online, or even a house rental directly through a development, like Rosemary Beach or Alys Beach in northwest Florida, there are some important things to keep in mind before taking the vacation rental-by-owner plunge. Here’s what you need to know:

1. Book from a reputable website.

Think reputation when choosing an online, owner-based, vacation rental service. Vacation Rental By Owner (VRBO) and HomeAway offer listings by owners across the globe, while location-based rental agencies focus on their particular city, similar to At Home Inn Chicago, where I just booked my Chicago rental. Why does this matter? Owners pay to include their listings on these sites, or pay the agency owner, so they have a vested interest in offering accurate photos and information.

Bucktown House, located in Chicago, is a fully renovated 1890s coach house available for rent by the day, week or month.

Bucktown House, located in Chicago, is a fully renovated 1890s coach house available for rent by the day, week or month. Image: At Home Inn Chicago

The living room in Bucktown House, located in Chicago: a fully renovated 1890s coach house available for rent by the day, week or month

The living room in Bucktown House is a beautifully decorated and comfortable-looking space. Image: At Home Inn Chicago

The kitchen in Bucktown House is modern, clean and perfect for eating in instead of dining out. Image credit: At Home Inn Chicago

The kitchen in Bucktown House is modern, clean and perfect for eating in instead of dining out. Image: At Home Inn Chicago

2. Talk to the owner.

When I first discovered Franklin House, a charming Victorian in Grand Haven, MI, I sent an email through VRBO. Franklin’s owner, Tina Elve, responded via email, but also made a point of calling me. She was checking me out, just like I was checking her out.

Franklin House is a charming Victorian in Grand Haven, Michigan.

Franklin House is a charming Victorian in Grand Haven, MI. Image: VRBO

When you’re having your conversation with the owner, find out who to call once you arrive, should there be any questions or issues. Memphians Lisa and Joe Namie bought their Seagrove, FL, vacation home in 2010, and they offer it for rental through VRBO. They also offer complete details about the home on their own website, TwentyThreePalms. Their guests have full access to them via text, cell phone and email, says Joe. “And, I have a set of five staff on the ground (in Florida) for things I can’t handle via phone, email or text.”

Memphians Joe and Lisa Namie bought their Seagrove, Florida, vacation home in 2010, and offer it for rental through VRBO.

Memphians Lisa and Joe Namie bought their Seagrove, FL, vacation home in 2010 and offer it for rental through VRBO. Image: Twenty Three Palms

A bedroom in the Namies' Seagrove, Florida, vacation home.

A bedroom in the Seagrove, FL, vacation home of the Namies is bright and welcoming for the entire family. Image: Twenty Three Palms

3. Make sure the rental fits your needs.

What’s your travel style? Taxi or public transportation? Quiet neighborhood or entertainment district? Make sure the neighborhood you’re considering has what’s important to you, whether it’s proximity to nightlife, a grocery store or boutique shopping.

4. Know what you’re renting.

Assume nothing, especially that your rental will be stocked with toilet paper. Be sure you understand what is and isn’t included. Are bikes available for use? Does it include linens, blow dryers, toiletries and paper products? What’s the parking situation? Is there a laundry room? Review what’s included in the rental, and be sure to ask if you have specific questions.

5. Respect the owner’s rights and property.

The bottom line with vacation home rental is that the property is a home, and many are owned and managed by individuals, not a development company. Don’t try to cram more people in than you told the owner you were bringing, be sure to report any breakages or mishaps and remember that, in many cases, the cleaning crew may be the owner, not a cleaning company. In other words, be a gracious guest.

6. Understand the departure procedures.

Sadly, all vacations must come to an end. What’s even sadder is when you discover that you’ve got to strip beds or start a load of laundry or dishes before you walk out the door. Even when you’ve paid a cleaning fee, it may not include laundering the linens or taking out the trash. Read the fine print in the departure section of your agreement.

My first ever-rental — Franklin House — led to a beautiful friendship between the Elve family and mine; our kids maintain close friendships, as do the adults. For me, that first foray into the online vacation rental world sold me on this mode of accommodation, and that’s what makes me comfortable taking that leap of vacation rental faith again and again.

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