Planning, Tips, Vacation Rentals

6 Tips for Picking a Vacation Rental

March 10, 2015 • By

Sometimes the Best Exotic Marigold Hotel is not a hotel at all.  Sometimes, the accommodation that fits your needs and budget is a vacation rental – an apartment, cabin, house or villa – in an awesome destination.

Right now, I’m planning an extended trip to Italy with five weeks in Venice, one of my all-time favorite cities.  For that amount of time, an apartment above a canal is the Room with a View I prefer.

I'm looking for a vacation rental in Venice - where shall I stay?

I’m looking for a vacation rental in Venice – where shall I stay?

(Yes, as I typed those last few words, I realized there are just so many movie titles I can rationally work into this post! So that’s it. I promise.)

Vacation rentals are great when you’re traveling with a group or staying longer than a few nights.

But can you really feel happy and safe, flying across the globe (or driving across the country) to bunk down in a stranger’s home? The answer is yes. You can!

I’ve booked vacation rentals across the US and around the world. And each time I’ve been happy I did. I have very specific criteria I use when booking – and you can use them, too.

1.  Use a Reputable Third Party to Book

This is rule number one.  Renting houses for the summer is nothing new.  People have been doing it for decades if not centuries.  At the turn of the last century it was all about hunting parties and picnics provided by a country-house staff. Now the options are endless.

I’ve used brick-and-mortar rental agencies in certain locations.  (These are more prevalent in resort type communities.)  But mostly I’ve used web-based services such as OneFineStay, Airbnb, VRBO and HomeAway.)

Use one you trust, or one that comes recommended by a friend (or trusted blogger!)

The room above is was in our vacation rental in Italy. We booked a villa for a house party for 13 friends, to celebrate my husband’s birthday.

By using HomeAway we were able to read reviews of the property made by previous guests, communicate privately with the owner/manager and pay our deposit without revealing our financial details to a stranger.  I loved this one, but some of our guests found it challenging! You can read more about this particular villa here.

2.  Look Before You Book

You’re going to need to spend some time on this.  But that’s also part of the fun.

When I book a vacation rental, I know what makes me comfortable and I search through loads and loads of online photos until I find it.  It may take days. And it usually takes several different websites – depending on where I’m going, for how long and how much I am willing to spend.

One site that unfailingly provides stylish holiday rentals is OneFineStay.  But they are not cheap!

This company only offers bookings in London, New York and more recently, Los Angeles and Paris.  OneFineStay is a curated service and worth looking at just to see some gorgeous interiors. They also provide elegant bath products, gift baskets full of tea and biscuits and even an iPhone or iPad loaded with local info when you arrive. Super nice. Great for a splurge or a big celebration, when you’re willing to shell out a bit more for something truly special.

By searching through several vacation rental sites, you’ll find a place that meets both your budget and your personal style.

3.  Every Detail Matters

This is the MOST important thing to remember.  As you pour over property photographs on various websites, look at the details.

EVERY. Single. Detail.

Specifically, look for a picture of the bathroom. If there are no photos of the most important rooms (kitchens, baths, bedrooms), move on.  Quickly! If an owner has only posted photos of the outside of the building, move on.

And if the photos are badly-lit, or if there are too many personal items visible, move on.

(In the bathroom, are there combs, brushes, toothpaste tubes and the owner’s bathrobe visible in pictures, for instance?)

Why should that be a criteria?  Here’s why. These pix are the owner’s best shot at marketing to you. If he can’t be bothered to clean up for the photo shoot, then he’s probably not going to clean for your arrival.

And if she can’t see how bad the photos look, she probably can’t see the other issues with her place, either.

Move on, I tell you – move on!

4.   Read the Fine Print

A reputable online rental site will have a standard list of amenities for each property.  Read that listing carefully.  Here are some things to look for.

Is the apartment on the fifth floor, but no elevator?  Is there wi-fi?  Cable or a streaming service, or a DVD library?  (Do you care?) Do you love a long, hot soak after a day of sightseeing?  Then make sure there’s a bathtub.  Is there parking, if you need it?  Or access to public transportation?  Is there anyone nearby to assist if you run into problems? What’s the cancellation policy? Don’t assume anything.

Example: here’s a beautiful English country cottage that I discovered on a walk while staying nearby.  Turns out, you can rent this beauty through The Landmark Trust which is a UK charity that saves historic buildings.

Don’t you get a romantic Jane Austin-style vibe when you look at the place?

But if you don’t read the fine print, you might be surprised to spend a week here without electricity or proper heat!  Fine, if that’s what you’re expecting.  A bit disconcerting if not.  And all the details are clearly stated in the listing. So do pay attention!

5.  Double Check the Location

An online service will give you some idea of the location of properties you’re considering.  They’ll show you a map or give you the name of a neighborhood.  The listing will probably say something like “5 blocks from the beach”, or “near the Art Museum”. On a map, you’ll at least see some of the major streets or attractions, if not the actual address. Now’s your chance to play detective.

If you’re happy with the photos and other details of a property, take all the location info you have and do an online walk through of the area.  Do a Google Street View “walk” up and down the streets.  Or search for images of the neighborhood online.  What do you see?  Are there people on the streets? Cars?  Are the buildings and yards well kept?  Are the roads narrow or wide? What kinds of shops or restaurants or businesses do you see nearby?  If any of the things you see make you uncomfortable, move on.

You and I may have different criteria, and that criteria may change from place to place.  But be clear on what that is, for you.  Graffiti, for instance.  Do you love it or hate it?  For me it all depends on context.  Certain cities have amazing street art and I love it. In other places, it may make me uncomfortable.  Only you know what works for you.

holiday rental barcelona apartment neighborhood rent flat house villa

A Barcelona Holiday Rental

Here’s a good example of why you need to do your homework:  Barcelona has a reputation for petty crimes against travelers, so when I visited for a week, I wanted to stay in a less touristy neighborhood.  And I was glad I did.  A friend staying in tourist-central had his wallet stolen!

6.  Establish a Rapport

Now that you’ve narrowed down your possibilities, make contact.  Don’t just book it immediately. Send a friendly first note explaining a little bit about who you are and why you’ll be in the area.  Let the owner or manager know what you liked about their listing and how many people are traveling with you.  Remember, these are people entrusting you with their homes and they need to feel comfortable, too. Then ask a couple of questions.

Personally, I don’t book until there have been two or three online exchanges.  I want to get a good feel for how accommodating the host will be – although I don’t ask him to jump through hoops.

I’m respectful when I ask to clarify something.   But I do want to get a feel for who they are, too.

Here are a couple of places I’m considering in Venice:

venice holiday rental apartment vacation travel rent apartment villa

Which of these apartments should I rent in Venice?

I’ve reached out to the managers and/or owners online, given them the dates I’m traveling and asked them each a few questions – but I haven’t booked yet.

But in a few months, I’ll be living like a local – however briefly – in one of these lovely flats.  I can’t wait!  (Stay tuned.)

BONUS: Book off-season, like I am, and most places will make you a special deal, especially for longer stays. It never hurts to ask!


Here’s a special offer! If you’ve never booked a vacation rental or holiday flat on Airbnb before, feel free to use my personal invitation for $25 off your first booking.  If you book through me, I get $25 off my next stay, too, so high fives all around.  And – Happy Travels!

Click Here to Get $25 Off Your First Airbnb Booking, by Using My Personal Invite.

Click The Picture Above to Get $25 Off Your First Airbnb Booking, by Using My Personal Invite.

And while you’re at, why not sign up for our regular Vacation Rental of the Week features and more?


You might also want to save this article for future reference…


Booking a holiday flat or vacation villa? Here are some tips for choosing the right vacation rental for you - from travel blogger and vacation rental expert Rover@Home.

Booking a holiday flat or vacation villa? Here are some tips for choosing the right vacation rental for you – from travel blogger and vacation rental expert Rover@Home.