Want to Book a Vacation Rental? 10 Questions You Should Ask

The Evolve Team
The Evolve Team
September 27, 2011

Ever had the inkling to book a vacation rental and not known where to start? With all of the sites available on the web (and we’re partners with many of them), we completely understand – it can be overwhelming to even start the process. While it’s not hard to book a vacation rental, it is hard to feel as if you’ve gotten not only the best deal possible but also understand everything that’s expected (on both sides – renter and owner) during your stay.


So – welcome to your online guide of the 10 questions that smart travelers ask before they book a vacation rental. We hope that this guide takes the guesswork out of the legwork for anyone who wants the freedom vacation rentals provide for their next trip. It’s a pretty simple list – so away we go!

  • What are the payment terms? Some vacation rental sites require you to pay the entire cost of your stay up front and others require a deposit. Make sure you understand what you’re in for financially as vacation rentals aren’t like hotels – you’re working with someone just like you who owns a great place and they want to make sure you’re committed to staying so they don’t pass up other rental opportunities.
  • Is a security deposit required? Depending on where you book, some vacation rental owners might require a security deposit for your stay. Understand how much this is, what it covers and how you will be refunded following your stay.  There is also an emerging trend towards offering Rental Damage Insurance in lieu of a security deposit (this is our approach at Evolve, through our partner Travel Guard). Just know that there are varying options available, depending on where you book.
  • How do I pick up the keys? You have to get in, right? Unlike hotels, most vacation properties will have arrangements made for someone locally to hold the keys. These can range from a local property manager to a friend or family member of the owner. Be sure to ask the hours for pickup and dropoff and how they prefer you to return the keys at the end of your stay.
  • Do I need to bring my own linens? Occasionally you’ll find that vacation rentals don’t come with creature comforts like bed linens. Know before you go and you’ll avoid an uncomfortable realization when you’re ready to call it a night!
  • Is the kitchen equipped? Just like bed linens, it’s smart to ask what’s available for use in the kitchen. This means everything from flatware to plates, glasses and pots and pans.
  • Whom do I call if I have a problem during my stay? We never want to plan for the worst, but make sure you have a phone number to reach someone 24/7.
  • What are the parking arrangements? Many condos and resort properties have parking permits and/or assigned parking. Be sure to ask and avoid getting towed.
  • How does the site that I’m booking my vacation rental through manage complaints? Most vacation rental sites have customer service contact information where you can report a transaction that’s gone awry. There are also many sites with robust peer review systems, where actual vacationers who have used the property can rate their experience. This is a great way to get a feel for the person you’re looking to do business with: the owner.
  • What amenities are available at the property? Don’t take all photos at face value. Smart property owners have professional photos taken to increase bookings – we’re sure you would, too! Be sure to ask if the things you see in the photos will be included with your stay (and don’t forget to ask about internet access!).
  • What is your cancellation policy? Perhaps one of the most important details, know the cancellation policy before you book. Many sites have trip insurance options that cost just a few dollars relative to the cost of losing the deposit you’ve placed on your entire stay. Know what your options and windows are and here’s a tip: schedule a calendar reminder a day before the cancellation policy expires so you don’t miss your window if you need to exercise it.

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