Booking a private villa for two people is one thing. Booking a private villa for 40 people staying five nights for a destination wedding is an entirely different sport.
I wasn’t just looking for a pretty house with a pool. I was essentially trying to find a temporary village where 40 adults could eat, sleep, shower, socialize, celebrate, and ideally remain on speaking terms by the time we all flew home.
Here are the ten things I looked for when booking a private villa for a large group.
Air Conditioning Throughout
This one was a non-negotiable.
We were traveling to Greece in October, so you might think air conditioning wouldn’t be particularly important. I wasn’t willing to gamble on that. Thank God because it was a steamy 85 degrees on our mid-October wedding day.
I checked that each bedroom had AC,, not just the common areas. Because “air conditioning” and “air conditioning throughout” are two very different promises.
A Private Bedroom for Every Guest or Couple
I wasn’t interested in creating a summer-camp vibe for our destination wedding.
For a group this large, finding accommodations with enough bedrooms, not just beds, was one of my biggest priorities.
A property might advertise that it sleeps 40 but that doesn’t mean 40 people can sleep comfortably. I refused to force guests who didn’t know each other to share a room and was not about to banish anyone to a sofa sleeper in a common space.
Private En-Suite Bathrooms
I wanted as few people as possible sharing bathrooms.
With 40 people getting ready for five days of events, I didn’t want multiple people who may or may not even know each other fighting for bathroom mirrors and showers.
Private en-suite bathrooms gave everyone privacy, peace of mind, and was one of the amenities that felt absolutely essential once everyone arrived.
Outdoor Space
Large groups need somewhere to hang out and get fresh air.
I looked for properties with patios, terraces, gardens, balconies, courtyard, and other outdoor areas where guests could spread out. Ideally, there’s private and shared common spaces for people to socialize in smaller groups or enjoy a coffee alone.
Swimming Pool
If you’re booking a villa in a warm-weather destination, a pool is almost mandatory.
But there’s a catch: read the pool details carefully. Is it heated? Is heating included? Is the pool open year-round? Is it seasonal? Is there an additional fee to heat it? Is there a minimum number of days heating is required?
These details can make a surprising difference especially if you’re traveling during shoulder season. A gorgeous infinity pool isn’t very useful if you discover after booking that it’s unheated, closed for the season, or costs several hundred dollars to make it remotely swimmable.
Proximity to Town
I wanted the accommodations to feel private without being in the middle of nowhere.
There’s a big difference between “peaceful countryside location” and “the nearest restaurant is 45-minutes away”. Because this was a five-day trip, I wanted guests to be able to get off property and explore the surrounding area. Ideally, restaurants, shops, bars, beaches, and other necessities are reasonably close.
This also meant considering transportation. Could people walk into town? Would we need taxis? What’s the parking situation? How difficult would it be for 40 people to get around?
A private villa is considerably more appealing when guests don’t feel trapped there.
Space for the Wedding Itself
This was one of the biggest differences between searching for a vacation rental and searching for a destination wedding property.
I didn’t just need a place for 40 people to sleep. We needed somewhere we could actually get married and hold a reception.
This meant thinking about practical stuff: Where would everyone sit? Where would dinner be served? Is there enough room for dancing? What happens if it rains?
Pretty pictures were nice. Functional wedding space was better.
Food: What Were Our Options?
I needed to know exactly what the food situation would look like before booking 40 people for five days. Could we have meals catered? Could we hire a local chef? Was breakfast included? Is the kitchen large enough for a group? Would we need to grocery shop and prepare meals and snacks ourselves?
The last option doesn’t exactly scream luxurious getaway.
Our group loves food, so meals were going to be a significant part of the experience. I wanted flexibility and convenience to have food brought to us rather than sending 40 hangry individuals into town to scrounge for meals.
Was it Actually a Good Value?
“Can we afford it?” wasn’t the only question. I wanted to know whether the property was worth the price.
That meant looking at the total cost and breaking it down by person. A villa might have an eye-watering price tag until you divide it by forty people and realize it compares favorably with booking individual hotel rooms.
Consider what’s included: accommodations, breakfast, cleaning, amenities, pool access, event fees, and other services.
The cheapest property isn’t necessarily the best deal. The goal was best overall value for our group.
Was There an On-Site Coordinator?
With a group of our size, I wanted someone who knew the property and local area better than I did.
An on-site coordinator or property manager can answer questions, help with logistics and maintenance issues, coordinate with local vendors, and generally be the primary point of contact if something goes wrong.
And something always goes wrong when you’re coordinating a destination wedding.
Having someone local was particularly valuable because I didn’t want to add front desk, transportation coordinator, and concierge to my list of bridal duties.
Ultimately…
I wasn’t looking for the most luxurious or Instagrammable property. I was looking for something much harder: accommodations that actually worked for 40 people.
Because when you’re booking a private villa for a large group, the dreamy, filtered exterior photos are just the beginning.
The real test is what happens when you take 40 strangers 7,000 miles from home for five days of festivities.
That’s when the villa either becomes a brilliant home base or an expensive group-project from hell.