Next Avenue Logo

How to Share a Vacation Villa and Remain Friends

The 8 questions to ask before you book a shared holiday home

By Candyce H. Stapen

A great way to vacation in princely luxury on a plebeian budget is to share a rental villa with friends and family. At a villa with multiple bedrooms, you can host your children and grandchildren or a gaggle of gal pals for that big birthday celebration at prices lower than what you'd pay for individual hotel rooms.
Costs range widely, depending on the property and its location. In general, a two-bedroom house (or even a condo) for a week saves you 25 to 40 percent of the cost of two hotel rooms of similar quality. On the other end of the spectrum, a weeklong villa rental on St. Barths in high season can you set you back several thousand dollars.
In any event, for the money, you get more space, more privacy and, depending on the villa, better views and more pampering, especially if you opt for a staff, a service that’s frequently available (especially on Caribbean islands). Typically, the cook makes breakfast and dinner and the housekeeper tidies up, adding lots of leisure time to your trip.
The villa I rented several years ago in Montego Bay, Jamaica, with my two sisters and their children came with a pool, hilltop views of the turquoise sea, and a staff, and it overlooked the golf course of the Half Moon Resort. What it didn’t have, I quickly learned, was enough bedrooms and bathrooms.
That meant I had to bunk with a sister, like we did in our school years. Also like then, she shoved my clothing and books into a corner in the closet, tossed her things all over “my side” and monopolized the bathroom. She thought nothing of coming in at 1:30 a.m. after dancing in Montego Bay, turning on the lights and talking so she could “wind down.”
Appropriate sleeping arrangements are by far and away the most important thing to consider, says Ellen Caywood, marketing manager for Wimco, an agency that rents villas in the Caribbean, Italy, the French Riviera, Greece and Morocco. Two couples, for example, should ideally rent a villa with two master suites. That way neither will have to cram into the twin-bedded room with a garage view while the other couple sprawls in the lavish suite with the Jacuzzi and the panorama of the sea.
Even singles need to be sure they’re getting a fair deal. Some are happy in a room with twin beds — and many people don’t mind sharing a queen- or king-size bed. But after my experience, I took a blood vow never again to share a room with my sister — or, if I could help it, with anyone.
But there’s more than just sleeping arrangements to consider. To return from vacation as close to each other as you were when you left, you need to be brutally candid ahead of time about a number of things. The discussion could get a little dicey, but better to do it at home, when cooler heads can prevail, than on-site, when it’s often too late to do anything about it.

(MORE: Gear Up: Great Travel Finds for the Mature Traveler)
Anticipate Everyone’s Needs in a Villa Vacation
Before you book airline tickets or put down a deposit, have a frank talk that covers these eight points. Plan to serve ice cream, sweets (or wine!) to make the honesty go down easier.

  1. Get everyone to discuss their desires and special requests. Do you want to be on the beach or within an easy drive to the water? Do you need a pool? Are you looking for Old World charm, funky island décor or modernist chic with flat screen TVs, a fancy coffee maker and a steam shower? There are no right or wrong answers, but what’s left unsaid could be the trip’s undoing.
  2. Talk about cleaning. Even in paradise, there are dishes to be washed, laundry to be done, beds to be made and floors to be swept. Either eliminate the issue by booking a staffed villa, or discuss how to share these duties. Remember: Friends can make lousy roomies. So be sure to let others know, for example, your penchant for towels neatly hung on the rack or aversion to dirty dishes left on the table.
  3. Share the initial work of researching villa rental companies. This way, the homework will go quicker. Find out what category of property the agency handles — basic or luxury, villa or condo — as well as what comes with the unit. Are sheets, blankets, towels, cookware, plates, utensils and cleaning equipment (vacuum, broom) included with the fee? Wimco specializes in deluxe villas in the Caribbean. Home Away offers a wide range of vacation and primary residences for rent in the U.S., Caribbean and Europe.
  4. Nominate a “point person” to handle all negotiations. Once you select a villa company, avoid confusion by appointing one person to deal with the company. If you book a staffed villa, be sure to discuss menus, special food requirements, mealtimes, tipping policy and special needs with the cook and housekeeper.
  5. Determine in advance how to split rental fees. Two couples in two master suites can easily halve the cost. But if you and your three kids take two smaller bedrooms and your brother and his son share the master suite, it becomes an math problem: Should he pay one-half, one-third or two-fifths of the rental fees?
  6. Establish how you’ll share food and liquor costs. If your sister and her husband want Caribbean lobster and curried goat for dinner, but you and your grandchild prefer chicken and spaghetti and meatballs, will you grouse at paying half the food bills? Likewise, if you drink just one glass of wine a night but your three friends have 5 p.m. cocktails every evening followed by a bottle of wine with dinner, are you willing to pay a quarter of the liquor bill? Beyond those costs, if there's no staff, you need to divvy up responsibilties of food shopping and preparation.
  7. Discuss your vacation rhythms. Do you get up 7 a.m. and head to the beach or the car for a full day of sightseeing? Or do you envision sleeping in, enjoying a late brunch and then visiting the nearest attraction? Differences in this department are a recipe for holiday disaster.
  8. Consider how to share a rental car. Face it: You and your housemates are never going to want to go everywhere together and at the same time. Think about sharing the car for one or two days of a week’s stay and then apportion the remainder of time. To eliminate problems, Caywood often suggests that couples rent two cars.

With honesty and forethought, you, your friends and your relatives will long remember this vacation for all the right reasons.
Candyce H. Stapen is a family travel expert, an author and the creator of FamilyiTrips travel apps for families ( For more information, go to

Candyce H. Stapen Read More
Next Avenue LogoMeeting the needs and unleashing the potential of older Americans through media
©2024 Next AvenuePrivacy PolicyTerms of Use
A nonprofit journalism website produced by:
TPT Logo