For the past five years, my friends and I have rented what we like to call “flophouses,” even though there is nothing flea-bitten about them. A farmhouse in Rhinebeck for New Year’s; a lake house in Copake for Labor Day; a 1970s modernist architect’s manor in the Berkshires for Memorial Day. We temporarily live well beyond our means in five-bedroom New England country homes where we’ll spend long weekends “flopping” around (reading, reclining, napping). We’ll take a short hike or piddle around a quaint little town, and then come home to cook extravagant meals in chef-kitchens before retiring to the living room to sit by the fire and sing obscure songs from Chess, the musical (we tend to get houses with pianos), or watch the Great British Bake Off in our sweatpants. Heaven.

A few summers ago, emboldened by these Airbnb success stories, we decided to attempt a European “flop.” I’d noticed through Instagram and Facebook that many people I knew to live in cramped Brooklyn apartments were posting selfies sipping white wine high above the Ionian Sea on their oceanfront Corfu estates. How was this possible? With a little help from their friends. The proliferation of extravagant home listings on sites like Airbnb and VRBO — made affordable if you bring enough people to fill the myriad bedrooms — has made traveling a group activity. (Friends of mine who live in London have been doing this ever since $45 Ryanair flights to Mallorca became a thing.) Why stay in a mediocre hotel when you can rent an entire Sicilian seaside manor house with your nearest and dearest? After going bleary-eyed scrolling through house after house, and debating which perfectly restored 17th-century villa had the infinity pool with the nicer view of rolling olive groves, my boyfriend and I — along with another couple and a single friend — decided to rent the Chianti country house of a Florentine architect for about $100 per person per night. We explored hilltop gem towns by day. At night, buzzed on red wine and full of pici, we’d cuddle up together and watch the English-language Korean daily news — on the channel the TV was set to, presumably by the previous guest — that we took an obsessive liking to.

The next summer, my boyfriend and I went to Hawaii for our vacation. It was lovely, we had a great time, we stayed in some really nice under-$200-a-night Airbnb studios overlooking the Pacific. But our tastes had become a bit more … refined. While walking along the beach in Hanalei Bay on the island of Kauai, I’d peek in at the ocean-side mansions, and think: That could be mine, if only I could convince enough friends to join me.

So the next summer, eight of us rented a house in Provence. The compound we found, owned by a Japanese woman who worked for the UN and had once been married to a French journalist, was right out of a European shelter magazine. The houses — that’s right, two of them, connected by a picturesque stone pathway — were filled with textiles and sculptures and books and artwork from her travels. There were pristine marble floors, a massive open kitchen with a view of rolling hills, and a beautiful swimming pool abutting a lavender field.

But, it turns out, living like a baroness can be a blessing and a curse. With eight people, as opposed to five, exploring the countryside and medieval churches was actually kind of unwieldy. Keeping track of everyone, taking multiple cars (or being stuck with one car when another broke down), figuring out who needed to be back at what time, proved tricky. Meals, too, were a bigger production: Cooking and shopping for so many people in a place where most supermarkets closed at 6 p.m. was a challenge. And going out to dinner with two cars, and everyone wanting some “magic water of the region,” was always a to-do.

What I learned from that trip, and the half dozen other houses I’ve rented with friends, is that you have to plan carefully. You need to establish up-front how you’ll handle the money and what activities everyone will want to do. I’ve also learned a thing or two about how to pick the right house: Look for a lot of books (which means the house is actually lived in), and a kitchen that’s open to the living area (or that’s big enough to contain couches) so that those tasked with cooking don’t feel isolated from the group. Make sure you’ve seen photos of all of the bedrooms — and that they’re more or less similar. A rule that I live by is that there should be one shower for every three people. Don’t be afraid to email your host a ton of annoying and specific questions. This past New Year’s, we did a flop in Connecticut. It was last minute and we didn’t ask enough questions; when we got there, we discovered the house was on a highway across the street from a McDonald’s.

The Connecticut house was … regrettable. But the Provence trip still turned out great, despite the challenges of the big group. We ultimately figured out how to navigate the size. We eventually settled into a rhythm with the excursions and the meal prep. And I have few memories fonder than drinking boxed rosé by the pool, listening to the chatter of my beloveds playing Settlers of Catan, while half-reading a very unserious novel and taking occasional breaks to walk a few feet and pick cherries off the nearby cherry tree.

18 Amazing Houses You Can Actually Rent with Your Friends »

Whom Do You Invite?

Choose your group carefully. Opposites don’t usually attract when it comes to group vacationing. Consider psychologist and travel-guide author Michael Brein’s three-point scale of compatibility:

1. Activity level. Are they high- or low-energy? If you plan to see a city by foot, for instance, you want people who can keep up.

2. Diurnal-nocturnal disposition. Do they prefer daytime activities or rowdy nightlife? The person who considers dinner to be a pre-game is going to have a very different experience than one who hopes to rest up and start the day early.

3. Time-urgency. Some people want to schedule every moment, while others prefer to be totally spontaneous. If you’re hoping to lock down two meals and three tours in one day, you’re going to be frustrated by the person who won’t commit to anything. 

This is even more important if you are renting a place where you and your friends are truly stuck together — like a yacht. “My favorite boats are the ones where everybody has the same idea for the trip,” says Kevin McLean, of The Yacht Week. “They could all be couples who want to eat big dinners and drink red wine, or people who want to stay out late and party on the islands. Either group is fine, so long as everybody agrees, generally, on what the vibe is supposed to be.”

Do You Have to Invite Jennifer?

No.

“Jennifer is a long-time friend of one of the girls who was spearheading a ten-person trip to Prague. She’s straight-up bad energy. She’s the kind of person who’s always exhausted or upset about something. We decided early on that we were only going to invite people who would be genuinely excited about the trip. For a couple of months we were discreet in the planning so that Jennifer wouldn’t find out about it. Then one day, while a few of us were at brunch, it came up. Jennifer perked up from her hangover long enough to say she’d like to join us. So my boyfriend says, ‘Crap! We already offered all the rooms to other people!’ This was a lie, but it motivated us to finalize our group. We had to act fast, before Jennifer came sniffing around again.” — Anonymous

To Airbnb or to VRBO?

Depends on what you’re looking for. Airbnb has over two million listings in 190 countries, everything from private villas to guest beds in a stranger’s apartment. The hosts tend to be young and chill, the homes slightly more modern and hip. But beware the professionally shot photos: You might be disappointed to find that the spacious, well-lit living room was just the product of a camera angle. 

VRBO, with 1 million listings in 190 countries, was founded more than a decade before Airbnb. Which means the crowd is generally older, a bit wealthier, and slower with technology. In this case, don’t be turned off by the amateur photography – the houses tend to be better than suggested by the photos. 

Is There Any Way to Avoid Endless Email Threads?

Doodle (free for iOS and Android) will help. The app allows you to blast out simple voting ballots, which your friends can reply to regardless of whether they have the app themselves. Use it to decide which villa to rent, how much seed money to put into your group vodka budget, and when to schedule your departure flight. Because it syncs with your calendar, Doodle can help work through scheduling dilemmas, too.

Do You All Have to Fly Together?

You don’t have to, but it’s a good idea. “Once you have more than nine people, you’re able to call up and deal with a group agent, who works on commission. That person wants to sell you more tickets, and I can get up to eight percent off of the going rate online. But the bigger perk is flexibility: With a group flight, you can change names on the reservation or arrange it so that one person flies back a couple days later. And say you have ten people committed to flying to Paris, and a few people who are still on the fence: Just book 15 tickets. You’ll put down a deposit, and the airline will give you a utilization date, which could be two or three months from the departure date. Now you can wait on your indecisive friends and continue recruiting people, and if you don’t fill the 15 spots before the utilization date, you can just hand the unused tickets back. So long as you’re using an airline with good group policies — Delta, United, and Southwest are my favorites for this — you’ll get your money back. Stay organized and there’s really no risk,” says Aaron Sanfield, founder of easygroupairfare.com.

Who Gets the Master?

Five room-picking tips you can learn from watching The Real Housewives, according to Vulture TV-recapper Brian Moylan.

1. The organizer gets first dibs. “It’s only fair. If Kyle Richards organizes the trip, you can bet your ass she’s going to take the best room. Nobody’s going to fight her on that.”

2. It pays to be obsessive. “Ramona Singer is the queen at getting the room she wants. The minute she arrives at a new house, she’s like, ‘Where’s the room? Where am I staying? What room am I getting?’ She keeps bitching and complaining until the rest of the girls are sick of it. They’ll give her anything to shut her up.”

3. It pays to have a roommate. “This is another famous Ramona move: She’ll team up with her bestie, Sonja Morgan, so that they can worm their way into a bigger room. She’ll say, ‘Since Sonja and I are sharing, we deserve the best room.’ Of course, Sonja doesn’t give a shit. She just rolls with it.” 

4. It’s not a good idea to show up late. “There’s usually one housewife who ends up arriving late because of scheduling conflicts. She’s definitely going to get screwed. The group that arrives first gets the first run of the rooms.” 

5. It’s possible to overthink the decision. “When the housewives visited Turks and Caicos, Sonja picked a room for her and Ramona to share. But Ramona wasn’t convinced it was the best, so she made a big production out of analyzing every room in the house. Nobody could settle in until she made up her mind, and in the end, it didn’t matter. ‘News flash,’ Carole Radziwill said. ‘All the rooms were exactly the same.’ ”

How Do You Stock the Fridge for Ten?

Cooking is always one of the pressure points for group vacations. Traveling chef Ian Buchanan says the key is division of labor: “Appoint one person for each important duty: cooking, cleaning counters, washing dishes, making supply runs. If you have multiple cooks, they can trade off the chef role each night.” Another key, says Buchanan, is a well-stocked kitchen. Here’s his weeklong shopping list:

PRODUCE (to last two days) Potatoes go with everything, so throw a five-pound bag into your cart. For aromatics, pick up two large onions and a head of garlic. Add four big heads of romaine, four cucumbers, and a pound of carrots (which you’ll shred) for appetizer salads. Then grab three pounds of tomatoes (for sauces and omelets) and three pounds of whatever vegetables look the freshest. For quick breakfasts and snacks, pick up a couple bunches of bananas, a dozen apples, and a couple pounds of berries.

MEAT & FISH (to last three days) Pick out some fresh fish for the first day, and 25 pounds of meat — split between chicken, beef, pork, lamb, sausage, and bacon — for the next few meals. It sounds like a lot, but a lunch portion is four to five ounces, and dinner is six to eight. Also grab a few packages of sliced deli meat for quick lunches and snacks.

DAIRY & EGGS (to last three days) Start with five-dozen eggs (that’s two per person per day). Then grab milk (three gallons), butter (one pound), and assorted cheeses (three pounds). If anyone’s lactose intolerant, make sure you know now. 

DRY GOODS (to last all week) These are your pantry staples: pasta, beans, grains, canned goods, olive oil, vinegar, cereal, crackers, condiments, and spices. In most cases, you only need one package (think one bottle of mustard, one bag of sugar, etc.). But this is where some degree of planning matters most: Are you going to have pasta every night, or rice-based dishes? Load up on whatever food you’ll be happy eating once everything else runs out. Oh —and this might seem obvious — but take stock of what’s already in your kitchen before the big trip to the supermarket. You don’t want to double-buy. 

How Do 12 People Get Around Tulum?

Whatever you do, don’t rent a van or anything else that assumes you will all want to do the same thing at the same time. “Over the past two years, I’ve been on four trips with friends. Three — a four-day trip to Montreal, a long weekend in Miami, and ten days split between Paris and Madrid — were terrific fun. But the RV trip through Iceland? That one was a disaster,” says Emily Chiu, an ad copywriter. “There were six of us, stuck together in a small hotel room on wheels. We were forced to agree on every single restaurant and route and detour. There were people who were sick of looking at waterfalls, or they were too cold to do anything in nature. We were arguing over the itinerary so much that we ended up cutting the trip a day short.” For her ten-person trip to Tulum, Mexico, travel writer Sophie-Claire Hoeller came up with a better plan. “We rented three cars. Some of us wanted to do yoga at the beach in the morning, other people wanted to sleep late. Some people wanted to go kite surfing, other people wanted to hang out at the bar. We’d always meet back up at some point, but being able to split up was key. That’s how we kept everybody happy.”

And Perhaps the Most Unpleasant Issue: How Do You Deal With Money?

There are basically two strategies for dealing with group expenses on the front-end, or on the back end. If you’d like to get the money out of the way ahead of time, decide on a budget and pool resources in the planning stage. “I’m planning a trip to Miami right now. I’m collecting $500 from everybody, and I’ll use that pay for the hotel, food, drinks, clubs — all of it,” says product manager Tim Holley, 30. “My friend who’s co-planning with me has used this strategy before. It solves a lot of problems: keeps people from breaking off into smaller groups, prevents awkward money conversations, stifles runaway spending. It allows you to focus on the important stuff. You just decide on a budget that everybody can afford, pool the money together before the trip, and plan your itinerary based on what you have to spend. If, by some miracle, we happen to come in under budget, I’ll just divvy up the money and hand it back.”

 If you’d rather divvy it up at the end, there’s an app for that. “When my friends and I were in Mexico, we all used this app called Splitwise,” says Hoeller. “Everybody on the trip downloaded it, we formed a group together, and then we used it to log all our expenses. We’d go grocery shopping, and instead of splitting the bill right there at the supermarket, one person would pay for everything and enter it into the app. At the end of the trip, Splitwise tallied everything up and showed us who owed what to whom. It’s not like we had to do a lot of calculations or anything. I can’t think of an easier way to keep track of group travel expenses.” — Clint Carter

18 Amazing Houses You Can Actually Rent with Your Friends »

*This article appears in the March 21, 2016 issue of New York Magazine.