Over the past forty years, I have traveled the globe staying in all sorts of weird and wonderful accommodations.

I’ve slept in five-star hotels and no-star hostels, rented palm-frond beach huts in Southeast Asia, and snuggled up in a wicker basket on a Chinese train station platform.

I’ve enjoyed nights on sofas and airbeds as a guest of new friends and contacts made along the way and even slept naked on a picnic table in Death Valley trying to find a way to break the mind-warping 113 F breathless midnight heat.

Nowadays, armed with a cell phone, a reasonably reliable internet connection, and a credit card or Paypal account, intrepid travelers can be a little more selective about where they lay their weary heads.

But while technology has made choosing and booking your accommodation easier, there are still many potential pitfalls out there.

Whether you are planning a globe-trotting gap year, a quick city break, or choosing a beachfront property for the family vacation, here are a few tips that may help you avoid too many surprises.

1. Location, Location, Location

This is definitely our number one concern. While you may think you are booking a house at the beach, a city center pad or an idyllic cottage, when you arrive the reality may not be all that

Like real estate agents and property developers who create niche names for ‘up and coming’ districts or ‘the next big thing’ neighborhoods – rental agencies and property owners can play loose and fast with the facts.

Yes, it may only be a ’15-minute cycle ride’ to the beach but that includes crossing 6 lanes of fast-moving traffic and traveling 3 miles on a busy road with no cycle path. Or your ‘2 bedroom pied-à-terre may be an apartment in the middle of a housing estate, not famed for its safety or tourist attractions, or the cottage might be so far off the beaten track that once your taxi drops you off you are stranded for the week.

While many properties, for security reasons, won’t share the exact address until you make the booking, using Google Maps, Streetview, and other such tools you can easily do a virtual walk through the neighborhood. If it reveals heavily barred windows, abandoned cars, and boarded-up storefronts, eight-lane highways, electricity cables overhead, or endless fields and woods, you may want to choose somewhere else.

2. Count the Beds and Baths

While the advertising may say “Sleeps 12”, check out where and how that is going to be configured.

Arriving after a long flight to find the accommodation in ‘6 -to a room in triplex bunks’ may not be the ideal way to start your well-deserved vacation.

Also, in a bid to get more of your ‘hard-earned’, the more unscrupulous vacation rental owners may have converted a dining room or a study into what they are calling a ‘bedroom’ purely by virtue of having a rolled-up futon mattress stuck in the corner.

If this is the case, Auntie Janet and her bad back are in for a big surprise.

Also, look out for a shortage of bathrooms. While every available square inch may have been kitted out for sleeping, where are all those guests going to shower, shave and go through their daily routines. Red flags should be waving and alarm bells ringing if the advertising says: “Sleeps 16, 3 bedrooms, 2 bathrooms.”

3. Read the Rules and Restrictions

The property you are renting is owned by someone.

They may live on-site, you may be renting rooms in their home, or spending your vacation in their second home. Understandably, they want to set some expectations as to what is going to happen while you are their guest.

Just because they have handed over the keys to their property for a day or a week or a month, they aren’t giving you ‘carte blanche’ to stage your own festival or rave, or to rearrange or redecorate the furniture or furnishings.

Nor do they expect you to sublet the property to your wayward cousin for his college frat-buddies reunion or to cram visitors and overnight guests where they don’t belong.

Many rental properties are in neighborhoods with Owners Associations and Management Companies so if swimming naked at 4 am in the community pool is your idea of a ‘normal vacation’, you may want to check out the rules which govern the property. Things like too many cars for the number of parking spots provided can create problems with neighbors, generate fines, and result in a knock on the door from the local sheriff.

When choosing your property to rent, think about how you want to use the space and if it isn’t compatible with the way the owners and their neighbors are living, this may not be the best choice for you.

4. Don’t Treat This Place Like a Hotel

This parental refrain to moody teenagers is just as valid for demanding vacation renters.

While you may have paid a lot of money for the use of someone’s vacation home, them being your butlers, cleaners, maintenance, and concierge team isn’t part of the agreement. If you are the sort who needs to call down to the ‘front desk’ on the hour every hour to request clean towels, cold bottled water, extra shampoo or to get the a/c adjusted, a hotel may be a better choice for you.

Again, you are staying in someone’s home. You will have to make the beds, wash the pots and pans, cook the meals, sweep up and take the trash out just like you do at home. Hopefully, you are doing this somewhere where the surroundings make it feel like a vacation or a trip worth taking.

5. Ask Questions Before You Book

When you are renting someone’s apartment or house it is, by design, a different transaction than booking a chain hotel room on a popular travel website.

You are, hopefully, creating a relationship with the property owners or their agents.

So, if having a coffee machine is important, if you need to have TVs in every bedroom, a washer and drier in the unit, or a step-in-shower with handrails, ask.

Asking questions also lets the homeowner know what your likes and needs are.

They may be able to provide unsolicited advice and ideas about things to do on your vacation – restaurants that cater to kids, the best place nearby to get your Mega-Choco-Mocha-Latte, where the best beach access is without the need to walk miles, or things to do if it rains.

Getting to know the property and the neighborhood before you book is not only a smart way to ensure the property will meet your needs, it is a great way to build your relationship with the property owner. After all, if your vacation is a huge success, you may want to book again –‘Same Time, Next Year’.

6. Study The Small Print

Nobody likes a surprise at the end of a wonderful week away.

As you pack up the beach towels and the last of the bumper box of breakfast cereal you over-invested in, keep an eye on the clock because buried in the small print of your rental agreement there may be big penalties for a late checkout.

Likewise, leaving dirty dishes in the sink, not cleaning the shower, or putting the trash out may see the total price of your vacation increase dramatically as the penalties and fines add up.

And the small print may also have some pretty excessive cancellation policy news in it too.

Some rentals only provide a 100% refund if you cancel more than 6 months before your proposed stay. In this COVID and travel restricted era, a lot can change by late Summer and you may find yourself on the thick end of thousands of dollars for a vacation you can no longer take.

7. Pick your Agency Carefully

Unfortunately, when there is money changing hands on the promise of something to be delivered in the future, there are scammers and fraudsters out there. The newspapers are full of stories of people who have booked wonderful apartments in Paris, London, Berlin or Los Angeles at terrific prices only to turn up at the address to discover the property either doesn’t exist or is the home of someone else.

Pictures can be scalped from Zillow or other sources and entirely convincing websites set up to make you believe the 1000 dollar-a-week, 5^th Avenue penthouse you found on craigslist is ‘the deal of the century.

IF your potential home renter wants money wired to them or doesn’t accept credit cards, that is a red flag. As with much virtual and online trade, you have to be extra cautious about who you are dealing with. While “too good to be true” deals can be enticing, it is wise to steer clear and work with the agencies, apps, and websites that are well established and offer payment protection and some recourse if things go awry.

And read the reviews. While they may not be 100% reliable, the big websites and agencies take them seriously and use them to filter out the less scrupulous providers who are just looking to make a fast buck at your expense.

Ready to book your dream vacation rental? Here are some options. Happy traveling!