What to Know When You Share a Vacation Rental

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It looked so good on paper — a week in a Caribbean villa with my two sisters, their children and mine. By sharing, we cut costs, gained more space than a hotel room and added such luxuries as a private pool. The rental house in Jamaica, our first villa rental, gave us time to reconnect instead of merely catching up between the turkey and apple pie at family gatherings. From the grade-schooler to the 20-somethings, the cousins bonded.

Over Scrabble on the veranda we laughed at anecdotes about Grandma Ray, who rationed french fries for svelte Aunt Ellie every Sunday because Ray told Ellie her bottom would grow too big. My nephew spoke about the difficulties and triumphs of teaching middle school, and my niece shared her joy at starting work at a New York City magazine. My son helped his cousins hone their golf strokes and taught his aunts tennis serves. My daughter perfected her backstroke, learning tips from her big cousins who spent summers as lifeguards.

My sisters and I agreed to split the house, rental car and food costs in thirds. Our hillside villa overlooked the turquoise sea and white sands of a resort where we had guest privileges. The villa’s staff cooked and cleaned, freeing us from chores. What could go wrong?

It turns out that even in the most picturesque settings, negative family patterns can pounce, clawing away at closeness.

Alas, our villa lacked enough bedrooms and bathrooms, causing me to bunk with my middle sister Rose (name changed to protect the guilty), just as we had growing up. 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 also thought nothing of coming in at 1:30 a.m. after dancing at clubs, turning on the lights and talking so she could “wind down.” After a few nights, I found quiet and the evening stars by bedding down on the veranda.

Write it in blood: A rental property must come with sufficient bedrooms and baths to provide a sanctuary for the adults.

One day we packed into the van and drove from Montego Bay to Dunn’s River Falls, Ocho Rios. Linking arms with the other tourists, we climbed the slippery rocks, getting doused by sprays and giggling. The next day, Joy (name changed), the oldest, commandeered the van to go shopping with Rose without telling me, leaving me scrambling for cabs to ferry six people to the beach and back.

Family rule two: Decide ahead of time how to share the rental vehicle. Not even sisters want to do everything together. Dedicate certain days for group exploration and other days for individual forays.

As the organizer, I found the rental, negotiated with the manager, informed my sisters and paid the upfront money. You know what’s coming. At the last night’s financial reckoning, recently divorced Rose refused to pay her share, arguing that we should cover her costs since Joy and I had husbands. After much talk, Rose plunked down about 25% of her bill, Joy added 20% to her payment, and as the family clean-up person and the contract signer, I paid the rest.

Family rule three: “Trust, but verify,” as Ronald Reagan said, is a good idea. Before the trip, ask each group to place their share of the fees in a vacation account managed by the trip organizer. See any hesitation as a warning of trouble ahead.

Despite the sister issues, I cherish the good moments and becoming closer to my niece and nephews. My children and I liked the privacy and pampering afforded by a rental home. Since our Jamaica trip we’ve booked many other properties — all vacations without my sisters.


A villa in Otago, South Island, New Zealand, provides a perfect spot for a family to gather.

When You Go

Popular vacation rental companies include:

Among the biggest vacation home rental companies in the world, HomeToGo compares more than 18 million vacation homes from 2,000 rental websites. Along with condos, homes and villas customers can find castles, boats, hostels and other lodgings: www.hometogo.com.

VRBO, part of Expedia Group, has been operating for 25 years. VRBO represents more than 2 million homes worldwide. Listings contain ratings and reviews, virtual tours and trip boards that allow groups to comment on the pros and cons of lodgings: www.vrbo.com.

Villas of Distinction vets each of its 4,000 properties in some 50 destinations, ensuring that the units maintain high cleanliness standards and feature modern amenities. Locations include Europe, the Caribbean, Central American and the United States. Customer service representatives are available 24/7: www.villasofdistinction.com.


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