Sharing a Villa with Friends: What Could Be Better?

by: Heather Warburton

Going on vacations with friends was one of those “adult” things I couldn’t wait to do when I was younger. It was one of those rites of passage that I dreamed of. I’d see groups of couples on vacation together in St. Barths, a table for eight at Maya’s filled with handsome men and sun kissed women, laughing and looking like they never wanted that week to end. I thought that was di rigueur for life as an adult. I realized later on, that getting to spend time with great friends even just once a year is such a treat.

With friends at a villa in Mykonos, Greece, WIMCO Villas, Villa Pool
With friends at a villa in Mykonos

I emailed my sister—an expert vacationer herself—about her experience renting a villa with friends, having done so in St. BarthsMykonos, and St. Tropez. Her response: “Renting a house with friends is SO MUCH FUN.” All caps…this girl doesn’t mince words! “You just have so much freedom to design the trip as you want. You can make yourself at home and enjoy lots of living space, but you still have the comforts of a hotel: daily maid service, arranging a chef, getting massages in the afternoon. And the concierge is a call away.”

While I am all for the hotel life, one of the great benefits of the villa experience is that you end up getting to bond more because everyone doesn’t retreat to their own hotel room at the end of the day. There’s also no need to plan to meet up. It can be refreshing not to have rigorously plan dinners and just let them happen a bit more organically. My friend Jenny often rents Villa WV ADO in St. Barths with friends and laughs over the impromptu parties they hold. “We cook elaborate dinners, have cocktail hour, invite people over we know and have met on the island, and lay by the villa pool. There’s nothing better than living in paradise with your best friends.”

WIMCO Villas, Adonis, WV ADO, St. Barthelemy, St. Jean, Family Friendly Villa, 4 Bedroom Villa, 4 Bathroom Villa, Pool, Villa Pool, WiFi
Villa WV ADO, 4 Bedroom, St. Barths

When you’re sharing a villa with friends, it also becomes easier to take advantage of some of those luxurious extras, like hiring a personal trainer, or arranging a chef. Not only is it more economical with a group, but it’s also more fun—a dinner at home becomes more exciting than a dinner out, and that Pilates class becomes a bit more bearable when you have a partner in pain. As my sister says, “We had a great Greek chef that WIMCO organized. He cooked breakfast every day for us and then one other meal (either lunch or dinner). I loved that when we woke up the coffee was already brewed, the pastries were on the table, and as people came up at their own pace he would cook eggs. It became one of the most fun parts of the day because it was this rolling breakfast, and no one had to deal with the cooking and clean up.”

I have a deep affection for vacations that bring friends together; they create the kind of memories that you laugh about years and years later.

Breakfast at the villa, WIMCO Villas, Travelling with friends
Breakfast at the villa

So in that spirit, here’s a few pieces of advice for renting a villa with friends:

  • If everyone has a mixed budget, go in the off-season (April 15th-December 15th, excluding Thanksgiving for the Carribbean, or try September for Europe). Prices are considerably more reasonable, and the per/room rate (if splitting equally) will absolutely rival, if not beat, a hotel’s prices.
  • If budget is the deciding factor, decide if you’re more of a going-out group, or staying-in group. Some people are fine with a simple bedroom and kitchen, and want to invest more of their budget in activities (like kite-surfing or boat excursions) or amazing dinners out. Others can think of nothing better than barbecuing at home and relaxing with their friends at their private pool, pouring from a bottle of Whispering Angel that was not marked up five times over—so they’ll choose a villa with bells and whistles. Decide which factor is more important to your group (and of course, there is always a middle ground).
  • Choose a destination that plays to your group’s strength: Are you major foodies? Think about Anguilla, St. Barths, or Capri. Friends from the West Coast or Europe meeting up? Consider how many stops you want to make and what destination makes that trek the easiest. (Our Air Desk can find you the best routes, too). Do you have an active group? Think about Turks & Caicos or Jamaica, where there are tons of watersports. See villas great for golf or tennis.
  • Pool: Unless you’re at a beachfront villa, a spacious pool is something to take seriously. Choose a villa that has tons of loungers and enough living space to feel like you could stay at your villa all day and never need to leave. This helps people feel relaxed and avoid any trace of cabin fever. See villas with incredible pools.
  • Cars: Consider renting enough cars where everyone can own a sense of independence. It’s nice to be able to cruise off on your own and not have to check in. My sister’s take: “In Mykonos we all rented cars, so some people could hang by the pool, while others would go to the beach. We were on the trip ‘together’, but had the flexibility to do our own thing when we wanted.”
  • Equal bedrooms: One of the great advantages of booking with WIMCO is that our Villa Specialists have years of experience and years of feedback from clients. They really know which villas are best suited for which type of clients—whether it’s a girl’s trip or a couple’s trip. If everyone would like to split the cost equally, having bedrooms that all have King sized beds will be important, as well as villas that have ensuite bathrooms.
  • Take advantage of our Concierge Service. To use an old quote of ours, we hope that getting there will always be as easy as being there. To that effect—we hope you use us to book flights, set up rental cars, pre-stock groceries, and arrange tee-times and the like. But we especially recommend it when you’re traveling with a group of friends. We’ll work with you to craft the perfect itinerary and make sure reservations are all set—after all, part of a great trip is the anticipation of being there.
Elia Beach, Summer in Mykonos, Greece, WIMCO Villas, Greek Vacations
Summer in Mykonos sounds about right. At Elia beach.

Not necessary tips, and definitely personal preferences, but some more ideas:

  • Check with your Villa Specialist on the speaker / Sonos “situation”. What is better than having a great playlist at your own private pool, or listening to a little Gipsy Kings while sipping a pre-dinner cocktail?
  • Instruct the guys in the group that bath linens are for the bathroom, and beach towels are for the beach. Common mistake. Men seem more prone to it.
  • Load up on easy-to-eat snacks, like a big bowl of grapes, or freshly cut pineapple, or a personal favorite, Chinese crackers. (Brie cheese also does the trick). No matter where the kitchen is, people will always congregate in the kitchen, and it’s nice to have something do in there.
  • Place the champagne glasses in the freezer an hour before you plan to have a toast. The Caribbean gets toasty, and there’s nothing better than a chilled glass of champagne….

Related: Discover 9 Mykonos beaches for every type of sun-worshiper!