Guest Post by Dan Weisman of

Vacation rentals are rapidly becoming one of the most popular options for travel accommodation because they provide the comforts of home while you’re on the go. More and more travelers are discovering that vacation rentals not only provide more space and amenities than hotels, but also that they typically cost less. However, for travelers new to vacation rentals, the booking process can seem foreign because it differs from the ease of online hotel booking.

That’s not to say that booking a vacation rental has to be difficult. If you follow the three steps below, you can book your first vacation rental and be relaxing in your personal paradise in no time…

1. Find Your Apartment, Condo or Home

The best searches begin on a dedicated vacation rental website such as FlipKey or TripAdvisor vacation rentals. Begin your search by asking yourself the “5 Ws”:

FlipKey Search

  • Where do I want to go? Start your search by choosing your destination. If you need inspiration, check out travel blogs and popular destinations on the FlipKey homepage.
  • When do I want to go? Include your travel dates to help you search only for available rentals. If you have flexible dates, then you can base your timing on the availability of the perfect vacation home.
  • Who do I want to go with? How many people are in your party? How many bedrooms do you need? Do you need a pet-friendly rental?
  • What amenities do I want? Once you have started to browse search results, you can narrow down your options. Do you need Wi-Fi and a hot tub? Filter the results to only show rentals with these amenities.
  • Why should I stay in one great home rather than another? On FlipKey and TripAdvisor you can read reviews by past guests and make an informed choice about where to stay on your vacation.

Browse the options and read reviews. No two vacation rentals are the same, so take some time to find the home that suits your needs. When you have found a couple promising homes, contact the owners/property managers through their online inquiry forms (most owners and management companies do not post their email addresses online). We recommend contacting at least five rentals to make sure you have some options. Feel free to ask specific questions about the property and the booking process, including pricing information.

2. Book Your Stay

Vacation Rental AgreementWhen you have received responses from several owners, you will be able to choose the right rental and make a reservation. Completing your reservation will include signing a rental agreement and sending a deposit to the property owner or manager. The property owner/manager will send you the agreement, which should include pricing information, policies, and check-in/check-out procedures.

Stay safe with your payment! When you make your deposit, avoid paying by wire transfer. Instead, pay using secure channels such as PayPal or Credit Card.

If you’re unsure of how to finalize your booking, don’t be afraid to ask. You can either speak directly with the property owner or manager, or you can contact FlipKey for advice.

3. Check-in and Enjoy!

Once you’ve finalized the rental agreement and made your deposit, it’s time to plan the rest of your vacation. Figure out your travel arrangements, pack your bags, and get ready to have a great time.

Vacation Rental KeysThe next step, checking in, can vary from one rental to the next, so make sure you have read the rental agreement and understand the procedure for arrival. You will need to get the keys to the rental, which are usually left in a locked key-box or at a central property management office. Before hitting the road, make sure you know where to pick up the keys and where to drop them off when you leave.

That’s it! Booking a vacation rental is pretty easy after all. Enjoy your stay and remember that you’ve moved beyond hotel rooms and are now traveling like a local – treat your rental as if it’s your own home and you’ll have an incredible experience.

Once you’re home, you can contribute to the community by leaving a review online at FlipKey. Relive your vacation and let other potential guests know what to expect.

Dan Weisman is a content specialist at, which features more than 100,000 vacation rental properties around the world. You can read more of his writing on The FlipKey Blog and connect with him on Twitter @flipkey.


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