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Remember those carefree college backpacking days? When a last-minute weekend trip meant throwing clothes in a bag and heading to the train station with nothing but a vague destination in mind? Back then, surprises were part of the adventure.
Fast forward to today, where surprises aren’t so fun anymore.
When traveling with family or friends in tow, the last thing you want when arriving at your villa is a surprise, as in, “Surprise – the A/C doesn’t work,” or “Surprise – there’s mold in the shower.”
Unfortunately, unwelcome surprises are all too common. The co-founder of Airbnb, Brian Chesky, recently made this confession to Travel + Leisure magazine. “The single largest complaint we get every single day is…
“This is not what I expected.“
The disappointments come in three flavors:
1.) Exaggeration – the description says it’s near the lake when it’s two miles away.
2.) Things not working or in disrepair – the espresso maker, the pool filtration system, the Wi-Fi.
3.) Errors of omission – the barking dog next door, the ant infestation, the cesspool that backs up after two showers.
Here are three stories about unexpected surprises putting a damper on a family vacation.
Horror Story #1:
Family reunion sabotaged
Imagine spending two years planning the perfect family reunion. You find a nice villa in Tuscany, coordinate umpteen schedules, book flights, and shepherd three generations 5,000 miles to the family’s ancestral hometown.
Everyone agrees – the pictures of the villa look amazing. And it’s with these images in mind that the group caravans from Amerigo Vespucci Airport to the picturesque Tuscan villa…
Only to discover that the driveway sits 53 steps below the front door of the villa. The only way into the house is by climbing the stone stairs with no handrail – an impossible task for the family matriarch 87 years old.
So she’s carried up to the house, fireman-rescue-style, where she remains housebound for the week, unable to take part in any day trips.
Having her mobility limited impacts the whole trip because no one wants to leave Nonna alone in the house. Plus, a big part of the trip revolved around her being able to see the old neighborhoods and sharing her memories with the kids and grandkids.
Image: ©paulpartridge
Lesson learned: Accessibility details matter. What seems like a minor inconvenience in photos can become a major obstacle for some travelers.
Horror Story #2:
Melting in the Mediterranean sun
The island of Paros in Greece can get quite steamy in August. After 16 hours of planes, trains, and automobiles, the first thing this family wanted to do was cool off. So everyone dropped their bags at the villa, grabbed a swimsuit, and raced to the beach for a cooling dip.
The first surprise was the wind. No one told the family about the Meltemi wind common to Paros from June to September. It can blow up to 50 mph, especially in the afternoon, and is strong enough to disrupt ferry service and sailing trips.
If you are a windsurfer or kite surfer, you love it. But lounging on the beach can be uncomfortable, with sand blowing into your eyes and stinging your body. It’s why seasoned travelers gravitate towards the leeward (southern) side of the island for beaches and villas in summer.
After an hour or so of eating sand sandwiches, Uncle Teddy suggests that an air-conditioned villa might be more enjoyable than playing Lawrence of Arabia. So the group retreats to their rental. That’s where they discover surprise #2: the air conditioning at the villa is not working.
A quick assessment of the situation: It’s 104° Fahrenheit. Villa guests include a dozen hot, tired, and cranky travelers aged 10 to 81. They’re strangers in a strange land. None speak the language. It’s Saturday. The villa owner lives in Paris. It takes a day to get hold of him and another two days before repairmen can be summoned. There’s no break in the heat wave. Sleeping is next to impossible.
When your entire vacation is 7 days, and the thermometer doesn’t go below 100 degrees, spending 4 /12 days sweltering without air conditioning is not ideal.
Image: ©hannahgullixson (Unsplash)
Lesson learned: When problems arise, having someone who can respond quickly is crucial. A villa expert with local connections can resolve issues in hours instead of days. And while weather patterns and seasonal conditions are important to know in advance, it’s even more important to have support when things go wrong
Horror Story #3:
The jackhammer from hell
Sometimes things seem too good to be true. And they are. A few years ago, an extended family wanted to do a Caribbean getaway in December. An 8-bedroom villa with a private beach, multiple pools, and even a swim-up bar was available at below-market price.
The location was ideal. The photos looked amazing. And when rumors circulated that the house next door was owned by a famous rock star, group excitement was at a fever pitch.
Until they arrived at the villa. Talking to locals, it came to light that the property was for sale – had been for a couple years. As a result, the owners hadn’t been keeping up with maintenance needs. What’s worse was what was happening at the putative rocker’s house:
Non-stop major construction – starring an inexhaustible jackhammer.
Want to sleep in… have breakfast on the patio… do yoga on the lawn… sip a mojito by the pool bar? Not during construction hours, unless you’re wearing noise-cancelling headphones (kinda puts a crimp on conversation).
Image: ©Alamy
Lesson learned: Sometimes the best deals are available for good reason. Current property status and neighboring conditions should always be verified.
These horror stories share a common thread: they could have been avoided with the right information upfront. While beautiful photos and glowing descriptions can be seductive, they often don’t tell the whole story. Critical details about accessibility, seasonal conditions, and neighboring properties can make or break your vacation.
So, how can you protect yourself from similar vacation-ruining surprises? The key is working with experts who know the right questions to ask and have vetted the properties they recommend.
The Challenge with DIY Villa Rentals
The rise of online vacation rental platforms has made it easier than ever to book a villa. But it’s also made it harder to separate the gems from the problems-in-waiting. Photos can be deceiving, reviews can be manipulated, and crucial information often goes unmentioned.
What to look for in a villa rental partner
1. Boots on the Ground
The most reliable villa rental partners have team members who regularly visit and inspect properties. They know the neighborhoods, understand seasonal patterns (like those Meltemi winds) and can spot potential issues before they become vacation-ruining problems.
2. Deep Local Knowledge
A rental partner should know more than just the property – they should understand the area. Which beaches are best for families? Where can you find authentic local restaurants? What’s the real travel time to attractions? This insider knowledge helps ensure your villa’s location truly matches your needs.
3. Recent, Verified Information
Properties change over time. New construction projects start. Maintenance issues develop. The best rental partners conduct regular property checks and maintain current information about both the villa and its surroundings.
4. Clear Communication
Look for partners who ask detailed questions about your group’s needs and preferences. They should be proactive about sharing potential concerns – like those 53 steps to the front door – that might impact your stay.
5. Problem-Solving Capability
Even with perfect planning, issues can arise. The best rentals come with a local concierge and proven processes for quickly resolving problems during your stay.
Image: ©paulpartridge
The Extra Mile Matters
While it might seem easier to book directly through an online platform, the cost of a vacation-gone-wrong far outweighs any initial savings. Working with experienced villa rental experts who take these extra steps can mean the difference between a dream vacation and a cautionary tale.
Don’t Let Your Dream Vacation
Become a Horror Story
The perfect villa vacation starts with having the right information and asking the right questions. While online booking platforms make it easy to reserve a property, they can’t replace the insight and security that comes with expert guidance – especially if you’re venturing to a place for the first time and don’t speak the language.
When everyone’s vacation dreams are riding on your choices, there’s no room for surprises. Make sure you understand exactly what you’re getting – and what you might be missing. The right preparation now can mean the difference between creating cherished memories or cautionary tales.
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