Renting a Villa for A Group Trip

When our client reached out for help planning a large (26 people) week-long reunion in Mexico, we considered all the options. When you’re planning for a large group trip like that you might look at all-inclusive, cruises, and more “DIY” options like a vacation home rental. This family considered them all before deciding on a fully-staffed villa, and it ended up being the perfect choice!

Why a Villa is Perfect for Groups

Villas offer a multitude of benefits that cater to the needs and preferences of multiple individuals, ensuring a seamless and enjoyable vacation experience. When you’re planning a large family reunion or a vacation with a big group of friends your goal in taking a vacation together is generally to enjoy each other’s company. You want to spend time with each other, not separated in your own hotel rooms, and a villa accommodates that in the most perfect ways.

Everything about the villa was stellar and everyone was extremely impressed and pleased with their stay.

The Riviera Maya Hacienda was nothing less than magnificent.  The pictures of the Villa do not do it justice.  We were in awe from the moment we walked in (Margarita’s waiting for us). And continued to discover so many lovely nooks and crannies.  Comfortable surroundings, soothing breezes and gorgeous bedrooms. 

Fully staffed villas provide ample living space to accommodate a large group comfortably, ensuring everyone has their own retreat and shared areas for communal gatherings. Having a dedicated staff on hand eliminates the need to divide tasks among yourselves. It allows you to focus on relaxing and enjoying each other’s company.

They often feature expansive outdoor spaces with private pools, gardens, and patios. Ideal for hosting barbecues, pool parties, and other fun activities. Villa rentals allow you to customize your stay to suit your group’s specific interests. Whether it’s exploring nearby attractions, embarking on adventures, or simply relaxing and enjoying the tranquility of the villa.

The whole week was a dream! We were all so grateful to have so much time together (and SO glad we weren’t at an all-inclusive!).

Even the most upscale villas can be more cost-effective than renting multiple hotel rooms. For families, reunions, or even just a couple of couples- the price per person often works out to be equal to a nice hotel or resort.

Sharing a villa with loved ones fosters a strong sense of community and camaraderie. It creates lasting memories that will be cherished for years to come.

What Does A Fully Staffed Villa Include?

It always depends on you and what you’re looking for, but generally, a staffed villa will include a butler, chef, housekeeper, and perhaps even child care. All the benefits of a hotel staff so that you and your group don’t have to worry about cooking, cleaning, or otherwise caring for your space.

The wait staff was MORE than phenomenal.  They became part of our family.  Our needs were met with great smiles and nothing was too much for them to provide.  Jorge, Patricio and Edam were so gracious and wonderful with our little ones.

In many Villas, you can decide how much staff you need. A butler, a housekeeper, a chef, a driver, child care? You can add these services as needed. Because they are with you the entire time you enjoy that personal luxurious touch.

The food prepared for us was out of this world; abundant, presented beautifully, and more than delicious.  Eating fruit and fish will almost be impossible now that we are back in the States! They did such a great job catering to everyone’s preferences.

Considering a Villa Rental?

  • Be sure you know what kind of vacation you want. If your idea of relaxing is curling up with a good book, make sure the villa has plenty of nooks where you can get some time to yourself! If you plan to do a lot of cooking, make sure the kitchen is big enough for everyone to roll up their sleeves and help out.
  • Choose your group wisely – make sure your expectations are the same and you know that spending a week together under one roof is a good idea!
  • Be clear on location- How far out in the country will you be? Will you need a car to get into town? Is it actually on the beach or is there a road down to the sand? What kinds of activities do you want to do with your group?
  • Remember that many properties have one-week minimums and rent from Saturday to Saturday.
  • Plan well in advance so that we can help you get the exact kind of villa you’re looking for with all the amenities you want!

If you’re starting to consider a villa rental for your next big group trip take a look at our more in-depth Villa Guide Blog . And then reach out! We’d love to help you plan the perfect group adventure.

Top Tips for Group Adventures

There’s a lot to consider when you’re going on a group trip — whether you’re planning an adventure with your best friends, a multi-generational getaway with the whole family or you’re embarking on a pre-planned group tour. There are some incredible benefits of sharing experiences with other travelers, but it does take some specialized planning. Here are our top tips for group travel of all kinds:

#1 Make Sure Everyone Is On The Same Page

From big factors like budget, destination, and travel dates, to small details like the number of beds you’ll need. It’s important to start with an open and honest discussion to ensure that everyone’s expectations align.

Do you want to spring for the ultra-luxury hotel with incredible views, pool, and spa — Or is this a more casual trip? Will you splurge on a once-in-a-lifetime experience like snorkeling with whale sharks? You don’t need to nail down exactly where you’re staying or what you’re doing yet.  Just get an idea of what kinds of activities, amenities, and styles everyone envisions for this adventure.

Be upfront about your boundaries, your priorities, and your budget. And allow space for everyone else to express their expectations. Make sure this vacation is a shared vision.

#2 Use Apps

There are a myriad of apps and technology to help keep everyone connected and on the same page. Utilizing things like WhatsApp and Google Docs to stay connected and share itineraries. Tricount or Travelspend will make keeping track of budget and spending so much easier. Make sure you have a plan of what you’ll use to communicate and keep track of costs before you go.

a group stands in front of a large fountain and beautiful vineyards in Napa Valley CA

[Photo Credit: Cailtin White via Shared Adventures — check out their girl’s trip to Napa here]

#3 Balance Free Time & Activities – But always plan food & drinks

When planning a trip for clients, we always try to create the perfect balance between wandering the beautiful streets, relaxing on your own, and pre-planned activities. It’s important to have downtime as well as scheduled activities. Remember, having too many planned activities in a day will leave everyone feeling tired and stressed. Plus, groups take a little longer to get from place to place because there will always be unexpected needs like a coffee, snack, or bathroom. So, leave yourselves breathing room in your schedule.

However, always have a solid dinner plan.  Nothing is worse than trying to decide where to eat when everyone is already hungry and finding that there is a 2hr wait because of your group size. You can always cancel the reservation if you change your mind.

#4 Everyone is good at something

Find the skill sets of the individuals in your group and utilize them! Does someone have a great sense of direction? They are now the navigator. Does someone speak the local language? They are the communicator. Two people with an artistic eye? In charge of photos. This will help spread out the responsibilities and tasks. It ensures that everything that needs doing is being taken care of and gives your vacation a collaborative feel.

Cruise ship group on the small luxury ship

[Photo Credit: Ann via Shared Adventures — check out her group trip aboard a luxury cruise ship here]

#5 Be Flexible & Have Fun

First, agree to have fun. Nobody likes the constant complainer on a trip – this is supposed to be a fun adventure! Entering the trip with a positive mindset from the beginning will ensure you’ll have a good time!

Second, figure out your non-negotiables and communicate them with the rest of the group. Find where you mesh together and where you might need to do your own thing. There will be a little compromise beforehand and some unexpected changes in the moment. So make sure you’re flexible in your plans and expectations.

Above all, remember that the best decision is any decision that gets finalized. Sometimes someone just needs to decide so you can have an experience rather than standing around trying to come to a consensus. Just make sure it’s not always the same person making the call, and remember to step up if no one else has a strong opinion.

Specific Tips for Group Tours

#1 Keep an open mind

On a planned group tour you’ll be in the hands of a trusted guide and might find yourself a little outside your comfort zone – but that’s part of the experience! To be able to do and see things you may never have thought of doing and seeing yourself. Be sure to join these groups with an open mind and willingness to experience new and different things.

#2 Be patient

Everyone travels a little differently – and that’s ok. While each group tour will tend to attract like-minded people, everyone has their travel quirks that you may or may not enjoy. Remember to be patient with others in your group. Especially since moving in a group will take much longer than if you were on your own. A little patience and kindness go a long way in creating a fun group atmosphere.

[Photo Credit: Ann via Shared Adventures – check out her recent adventure to Thailand here!]

#3 Ask Questions

Your tour guide is there to answer all your questions! They often have more in-depth knowledge than just what’s on your itinerary – so be curious! If you start to wonder about something, speak up and ask. Similarly, ask questions of your fellow travelers. Group Tours are a great way to meet interesting people, and make new friends from all walks of life – so indulge in curiosity and ask away!

Specific Tips for Friend Groups

#1 It’s more about the Group than the Destination

The destination is incredible and worth enjoying, but the point of a group vacation is to spend time together! To get away from the day-to-day minutia of life! Carve out time to be in the moment, chat and enjoy each other’s company. Don’t get too hung up on ‘seeing it all’.

#2 Have Some Alone Time

While this adventure is about spending time with your favorite people – sometimes you need a little alone time to be your best self, and that’s ok. You don’t have to do every single thing together.

#3 Establish a leader

Early in the process, pick someone who will be the leader. The organizer, the person who best understands the needs of the group and is willing to take on the final decisions. While it should be an overall democratic process – having someone as the point person for your travel agent or general organizer will be a big help.

[Photo Credit: Ann via Shared Adventures — check out her group trip to the Galapagos here!]

Specific Tips for Multi-Generational Adventures

#1 Cater to Everyone’s Interest

a large family photo in front of the rocky mountains

More often than not, you’ll find that not everyone is interested in seeing the same things – and that’s ok. Make sure to have a balance – a little bit of something for everyone. And a few things that everyone will enjoy.

#2 Schedule time to sit and soak it in

Make sure to schedule frequent breaks and times to just enjoy being together. Whether it’s a long lunch, time to sit in the park, or relaxing together on the beach. Don’t let the vacation zoom by with too many plans and activities.

[Photo Credit: Ginny via Shared Adventures]

#3 Plan for bathroom breaks

The much older and much younger generations tend to need more bathroom breaks and it’s worthwhile to do a little planning ahead of time. Make sure there’s time in the schedule and, if you’re on a road trip or walking around a city – you know where the bathrooms are.

We hope these tips have you feeling ready for your next group adventure! The earlier you start planning the better — so let us know what you have in mind and we can help you every step of the way!

Five Destinations Ideal for Group Travel

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In 2022 we are all focusing on connection — finding ways to share experiences and create memories with those we’ve missed spending time with. But deciding where to go for a multi-generational family, reunion, or friend-cation group trip can be tricky. You want to find somewhere with a little something for everyone. Someplace where you can feel safe, and a destination where you can spend a lot of quality time together. And spend time soaking up everything you’ve missed over the past two years. Here are our suggestions for some small-group destinations that would be perfect for this year’s shared adventure:

Mexican All-Inclusives

Sun, beach, and warm sand for the whole family to enjoy! Plus the added luxury of all your meals and drinks included (and no one has to cook or clean!) With a big focus on relaxation, this is a great destination to reconnect. Many all-inclusives have casitas, villas, or stand-alone suites with their own pools. Which gives you a great sense of seclusion and privacy. Plus, they offer a wide range of activities for all ages and interests. You can just enjoy each other’s company without the stress of trying to get to the next landmark or attraction or figure out where to go for dinner that evening. For bigger groups, groups with younger children or those who love chilling on the beach – The Mexican Riviera has a lot to offer.

Costa Rica

a group of friends white water rafting down a river in Costa Rica

With a tropical climate, plenty of private villas, and beautiful beaches, Costa Rica has a lot in common with Mexico. Costa Rica, however, has a greater sense of adventure. Offering a multitude of outdoor activities from hiking to rafting to ziplining. It’s a great destination for friends who love the outdoors and want to have an active vacation with only a few beach days thrown in. Or families with kids who love animals and would enjoy the variety of wildlife in the area. Plus, Costa Rica has a major focus on sustainability, making it a top choice for your eco-conscious friends.

[Photo Credit: Alex via Shared Adventures]


Often seen as a ‘romantic destination’ (which it can be) Italy has a great advantage for groups — there’s a little bit of everything. If your group has a wide variety of interests, Italy is the place to go. History buffs, foodies, shopaholics, beach bums, and outdoorsy types alike will all find something to enjoy. You can head north to the Dolomites and the fashionably stunning lake district. Or head south into the wine-soaked hills, the small historical cities, and the beautiful beachy coastline. Cities like Rome and Florence offer history and shopping around every corner. And not too far away you’ll find breathtaking coasts and mountains. Italy is all about coming together for an aperitivo or a delicious meal to share stories about the day’s discoveries and adventures. And your accommodations can range from charming local hotels to sleek luxury resorts, city-center apartments, or private villas in the countryside.


a Castle Ruin in Conwy Wales

For those who aren’t looking for a tropical climate, Wales is great for a multi-generational road trip. The dramatic coastline and beautiful national parks offer a lot for those who love to be active (and for those who prefer a gentle stroll.) Certainly, you’ll find plenty of historic castles and quaint seaside towns to enjoy together. There’s plenty of room for kids to run around, and adults to follow. Above all, there’s something slow and relaxing about the pace of life in this intriguing countryside.

[Photo Credit: Ann via Shared Adventures – read about her UK road trip here! ]


Whether you head to South Africa, Tanzania, or Kenya – going on safari with your group of friends or family is a magical journey. Share the once-in-a-lifetime experience of seeing incredible wildlife up close. And share stories each night over a gourmet meal back in camp — safaris offer a complete change of scenery away from the hustle and bustle of daily life. Additionally, safaris are scheduled and guided to maximize the wildlife (and scenery) viewing potential, making planning your day a breeze. As a result, you have more time to focus on creating memories that you’ll be talking about for years to come. Since most safaris are group activities anyway, why not take your own private group with you?

Vacation Pods

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If 2020 has taught us anything, it’s the importance of connecting with loved ones. Most of us have had plenty of family time at home by now, and are yearning to find a way to get outside the same four walls. Finding a change of scenery, sharing adventures and laughter with friends, letting your little ones get out of the house and be around people their own age — this almost seems like an impossible dream. But there IS a way to make the impossible possible: Vacation Pods. This travel trend is all about minimizing risk while satisfying your urge to travel and your need for connection. Here’s all you need to know:

What is a Vacation Pod?

Vacation Pods (also called travel pods or quaranteams) are a new way of taking a vacation with others while minimizing the health risks typically associated with group travel. A pod is a group of families and/or friends (who follow and value the same safety standards) taking a trip together. This can include two or three families merging together or a group of friends. Typically, pods should be kept to 10 people or fewer.

By staying in the same group and with the same guides through the whole trip and not mingling with those outside your pod, you reduce risk. Of course, any travel will always carry some risk of infection and spread, and it’s important to stay vigilant, but pods can help you control that risk and keep it to a minimum. Pods also allow you to split the travel costs, making your vacation more affordable.

three young boys jumping into an infinity pool

Pods offer you peace of mind and a sense of safety, while still sharing an adventure. They’re particularly great for families who want to give their children a chance to socialize and play with other kids. Pods are a perfect way to salvage that annual vacation you look forward to every year (as long as you make smart, thoughtful choices.)

[Photo Credit: Marc Tutorials via Pexels]

Keys to making your Vacation Pod great

Same risk-aversion attitudes: When considering who you want to travel with, make sure that you have the same attitudes, priorities and risk aversion thresholds. Find like-minded people who agree with your risk comfort level.

Trust: Forming a vacation pod with another family or two involves a lot of trust. You’re trusting your pod with your health and they’re trusting you with theirs, so you want to make sure to choose people whom you trust to strictly follow the guidelines the group has established.

Communication: When you’re planning any group trip you have to agree on the destination, the activities, and who’s sleeping where. With a vacation pod designed to minimize the risk, there are few more details you need to work out.

a woman wearing a mask with a small backpack on a forest trail

Discuss in detail the precautions you’ll take before the trip. It’s best to negotiate to meet the needs of the most at-risk person. What makes this trip possible for them? Whether it’s everyone getting tested a few days before or going through a two-week quarantine or both. Consider everyone’s habits and who they’re exposed to daily. Make sure everyone agrees to follow social-distancing guidelines and wear a mask when out in public or with people outside of the pod.

[Photo Credit: Tsunami Green via Unsplash]

two women having a picnic in a field with a green tree

After the pre-vacation arrangements are agreed-upon, it’s important to discuss the safety guidelines you’ll follow while actually on the trip. When are masks required? How much exposure are you willing to risk? Are take-away or grocery runs ok? Or do you want to buy all the food beforehand and cook it on-site? We recommend having a zoom call and writing down all the agreed-upon guidelines so there’s no room for misinterpretation.

[ Photo Credit: Toa Heftiba via Unsplash]

Finally, make sure you have some back-up plans in place. Ask yourselves if/then questions. What if someone tests positive? What if someone’s test results don’t arrive on time? Having a clear plan will ensure that your vacation is as relaxing and worry-free as possible.

Where Should You Stay?

These days, vacationers the world over are looking for private, controlled spaces, away from the crowds, and with plenty of outdoor activities. Vacation pods are no different.

Many resorts and hotels are offering pod-friendly accommodations, where you can rent out an entire floor for your pod! These pod packages often include room service, local take-out, in-room entertainment, balconies and large suites that can be configured to perfectly suit your group. Some places have private pod events like wine & chocolate nights or a murder mystery party. Others offer you a private elevator and dedicated beach beds.

a private pool with two lounge chairs and a hotel room at a resort tropical

Some hotels and resorts even offer detached villa-style rooms with private pools. Depending on the size of your group, it can work out to be the same price per person as renting a couple of mid-range hotel rooms.

[Photo Credit: Anam via Unsplash]

a cabin in a snowy landscape across emerald lake, Canada

If you’re looking for even more control over your environment you and your pod can always opt to rent a stand-alone space. Choose from a cozy cabin, a luxury condo, a chill beach house, or a spacious Villa! The possibilities of where to stay with your vacation pod are endless!

[Photo Credit: Alex Hawthorne via Unsplash]

Utilizing the Experts

Ready to start but not sure how to narrow down the endless possibilities? We can help you find the right place to stay with the strongest health and safety protocols (and the right amenities) to make everyone in your pod happy.

Even before the pandemic, organizing a group trip meant juggling multiple opinions, priorities and budgets, but now you also need to know the ins and outs of local COVID regulations. This is where we can really help! We’re staying up-to-date on all the rules, and can keep you advised on the ever-changing local guidelines. We can also find you pod-friendly private tours or specialized events to enhance your trip!

Forming a conscientious vacation pod is becoming the future of travel. Finally getting out of the house and being able to enjoy a little company in a risk-minimal way is great for everyone’s mental health. Let us help you make it a reality, so all you need to do is enjoy the breath of fresh air and a change of scenery with your favorite people!

a group of people standing with their hands up facing a sunrise
[Photo Credit: Min via Pexels]

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)