Little Queen, Rome
Read About Can't Miss Places, Travel Tips

Tips for Booking the Best Vacation Rentals

Leasing vacation rentals abroad can be a scary proposition. What if the property isn’t as advertised? What if the owner reneges on the deal and you end up homeless? Will you have the amenities you’re used to? Will your credit card be safe when you pay for it? Where do you even look for a place?

For any or all of these reasons, many people give up on their dream of renting an Italian villa or English cottage and lose out on rich, cultural experiences. Vacation rentals provide travelers the opportunity to live locally.

Working With the Right Company For You

When jumping into the vacation rentals market, I investigated over a score of companies. It’s nerve-wracking to think about the negative scenarios, so I did due diligence. First, I consider the vacation rentals website. If it looks dodgy, I assume the company is. The second aspect I evaluate is customer service. If something goes terribly awry with my vacation home abroad, I want to easily contact the company so they can help find a solution (the main reason I paid a high service fee). If I’m unable to locate/contact customer service during my review period, then I’m probably going to choose a different company. Thirdly, I want a reputable company that will handle payments and keep my financial information safe. Lastly, I look for listings that appeal to me. Couch surfing may be the current rage, but even if a company has a million sofas for rent, I still don’t want to hang out in my pajamas with strangers.

HomeAway (also owns VRBO and interested me because of their “Book with Confidence” program. According to their website, they offer rebooking assistance, security deposit protection, and payment protection. They also offer 24/7 customer service. Unlike many vacation rentals sites, I easily found a telephone number. When I tested it out, they answered—a huge bonus! My email query also received a response. HomeAway charges a service fee; property owners determine if they will charge cleaning fees, require security deposits, or allow cancellations. When looking in Florence, I found many property owners who were quite flexible in their terms. Being able to cancel up to 30 days out gave me peace of mind. HomeAway hosts over a million listings, so there are lots of options.

There are more aggregator sites than HomeAway, such as: Airbnb (see below for savings), Housetrip, Flipkey, Holiday Lettings, Vacation Home Rentals (all four owned by TripAdvisor), Roomorama, 9 Flats, and Wimdu. One good thing about sites with many vacation rentals is there are generally more reviews of the property and its owner. If big websites overwhelm you, try a local rental agency or type in the name of the city and “vacation rentals” or “holiday rentals.”

For an utterly charming and unique accommodation website, visit Into History. Founding partner, Gery de Pierpont, and his fellow partners have curated historical properties across sixteen European countries. If you’ve ever wanted to spend a night in the past, Into History gives you the chance to do so. Guests can choose from many beautiful and culturally-rich accommodations such as: a 15th c. Italian palace in Rome, a 14th c. French castle, an 18th c. Irish manor house, a 15th c. Czech monastery,  a 17th century Belgian mill, and an Italian Stone Age cave! Into History provides travelers with vivid descriptions and captivating histories of the properties to pique their interest. All the necessary details are provided, including the one important to every lover of history—the age of the property. When you check the availability of a historic property, Into History directs you to the place’s website so you can book directly. Even if you’re not going to Europe soon, I suggest visiting the website and feasting on the properties, as well as some of the lovely articles.

Finding the Best Vacation Rentals

For finding the best vacation rentals, get your spreadsheet ready. I’m not joking. I make a list of my dream property’s details and then each of those features gets a spreadsheet column. If a property has a certain amenity, it gets an “x” in that column. With one glance, I can see how close a property is to my desire.

Here are aspects I consider (comments are for nightly prices under 130€):

  • Location—within walking distance of favorite historic sites & close to public transport
  • Outside space—I love a terrace, balcony, or garden.
  • Air conditioning—some European places don’t have this or it’s only in main living space
  • Wi-fi available?
  • Television?—I’ve found properties without televisions
  • Bed situation—studio, separate bedroom, size of bed (European sizing is different)
  • Tub/shower—Tubs are rarely available at this price. Check reviews/photos to see shower size.
  • Are linens & towels provided?—this is pretty standard, but still good to check
  • Coffee maker? Microwave?
  • Type of kitchen (full or kitchenette)—Stove (number of burners?), size of refrigerator (mini isn’t abnormal), are there pots, pans, utensils, pantry items, etc.?
  • Washer? (Don’t be surprised if there isn’t a separate dryer.)
  • Ironing board/iron?
  • What floor is it on? Is there an elevator/lift?
  • Are the rooms bright? What size is the property?
  • Price? Cleaning fee?
  • Is there a refundable deposit? Is there a non-refundable deposit? If the latter, I wouldn’t book.
  • What are the cancellation terms? I want reasonable cancellation.
  • How are the reviews? Any warning signs?
  • Other—I note cool things, like if the property is historic or has a view. Also, this is where I put items to investigate further such as odd house rules or comments indicating shared common areas.

It may seem intensive to do all this leg work, but in a way it feels like part of the vacation. I get to immerse myself in the city of which I’m going to stay. I play around with Google Earth and look at the neighborhoods of the properties. Using Google maps, I check out what restaurants, shops, and attractions are near my top contenders. I email the property owners to see if they return my inquiries (if they don’t, I don’t rent from them) and start forming a relationship with them. By doing all of this preparatory work, I ensure that I’m setting myself up for a wonderful holiday and leasing my dream vacation rentals.

**If you would like to save $35 on your first Airbnb rental, contact me below and I can share a referral credit with qualified friends.

Like what you just read? You can support me by following my blog and leaving comments–I love to hear from my readers. Happy travels! Amy

Are you looking for a fun small-group tour in Europe or the United States? Roaming Historian is an affiliate of The Tour Guy. They offer unique experiences, small groups, special access, and exceptional guides. Use our affiliate link, Tour Guy, or visit our page dedicated to them to learn more about the Tour Guy.

Disclosure: Roaming Historian may derive revenue from affiliate links and other sources, which helps offset the costs of bringing you the information we do. The blogs and reviews posted on this website are of our own opinion though.


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