The Ultimate Guide to Planning a Destination Family Reunion Everyone Will Remember
Are you dreaming of planning a family reunion that your family will remember for years to come?
Ok, let’s be real. Most family reunions aren’t anything special. They’re backyard barbecues with the same food, the same boring conversations and the same routine. It’s nothing memorable.
Until you take it “destination”.
Destination reunions are booming. A travel survey by Squaremouth predicts that 47% of travelers booked multigenerational family trips in 2025, up 17% over 2024.
Family vacations are here.
…but planning your family’s destination reunion takes more than booking a holiday villa for everyone to stay at. It takes serious planning. Coordinating with multiple families to find a location and travel dates that everyone can attend.
Oh, and activities. Everyone wants to do something different.
Here’s the secret…
Having one luxury villa rental that accommodates your entire family is the first step to taking stress-free family vacations. Places like this 10 bedroom villa rental Costa Rica with chef have private accommodations and on-site staff dedicated to making your large family feel right at home.
You’ve got enough to worry about when planning your next reunion. Let the experts at your villa handle the rest!
What you’ll discover:
- Why You Should Consider a Destination Reunion
- How to Choose Your Family’s Perfect Location
- Booking the Right Villa Rental For Large Groups
- Family Activities That Everyone Will Enjoy
- Saving Money: Budgeting for a Destination Family Reunion
Let’s go!
Why Should You Plan A Destination Reunion?
Let’s face it. Family reunions are tough. Someone has to plan it. Someone has to clean. Everyone has to travel.
With a destination reunion, you take everyone out of their element and force them to enjoy each others company. It’s a vacation for everyone.
Keeping the whole family in one private villa also means that everyone has space to relax without worry. You aren’t cramped in a hotel room or someone’s backyard. And staying in a luxurious villa with all of your loved ones means you have staff looking after you.
More family travel means more opportunity for memorable reunions.
Research from Hotel Management stated that 77% of travelers say multigenerational trips are primarily associated with a life event, such as family reunions or milestone birthdays.
Traveling with your family is no longer a casual vacation. People are taking large trips to spend quality time together that they’ll remember for a lifetime.
How to Choose The Perfect Destination for Your Family
If you want your reunion to go smoothly, picking the right destination is critical. If your villa is difficult to get to or something comes up with travel, you could be in for a stressful reunion before it even starts.
Keep these tips in mind when searching for the perfect spot:
Fly in. Fly out. Easy.
Make sure your villa has access to a major airport. A short cab ride should get you there. Too many families get stuck dealing with multiple layovers and delays because their villa wasn’t near the airport.
Weather will matter.
Don’t pick a destination based on activities alone. Would you want to be at the beach if it’s raining? No. Do you want your entire family stuck inside your villa while it rains? No.
Choose your destination with weather in mind.
Make sure there is something for everyone.
It can be tough to find something that entertains toddlers and grandparents equally. But when you pick a destination, make sure there are things for everyone to do. Sporting events, museums, outdoor adventures.
Those with access to outdoor activities are always a great choice.
Check infrastructure.
Having reliable cell service, internet, restaurants and roads near your villa is a huge help. Medical facilities should also be nearby if you’re bringing elderly relatives or children.
Popular destinations with great infrastructure for families include Central America, the Caribbean, and Southeast Asia.
How to Choose The Right Villa Rental for Large Groups
The biggest mistake most families make is booking multiple hotel rooms.
Suddenly you’re staying on different floors of a hotel with no place for your family to gather. Not only is that not ideal, but hotel rooms aren’t made for large family gatherings.
So how do you keep everyone together? Book a luxury villa rental that accommodates your entire family.
Staying in a luxury villa instead of a hotel has many benefits:
- Group space: Plenty of room for your entire family to gather together in one place.
- Privacy: While you can all stay in one villa together, everyone has their own private bedrooms and bathrooms.
- On-site amenities: Large villa rentals often have private pools, gardens and entertainment areas your family can enjoy.
- Staff: Many luxury villa rentals offer private chefs and housekeeping services.
You no longer need to worry about booking hotel rooms for your entire family. Not only can you save money by booking a private villa instead of hotel rooms, but you’ll have everything you need in one place.
Planning Activities For Every Age Group
Here is where most families go wrong with their destination reunions…
They plan activities for their kids without realizing their teenagers want to do something different. Or their parents won’t be able to join in.
Make sure you plan some things for your entire family to do, as well as smaller independent activities that different groups can do on their own. With that being said, some great activities for the whole family include:
- Day at the beach or villa pool
- Renting a private chef to cook a group dinner
- Tours or sightseeing around local attractions
If your kids want something a little more exciting, consider these adventurous activities:
- Zip-lining, kayaking, snorkelling
- Nature hikes or guided tours
- Water parks and boat tours
And for everyone who just wants to sit back, relax, and rejuvenate:
- Book a spa day
- Read a book by the pool
- Join a morning yoga session or take a walk
Don’t over-plan!
Build in lots of downtime so your families can relax and do what they want. Some of the best reunion moments come from spontaneous adventures.
Saving Money: Budgeting For Your Next Destination Family Reunion
Destination reunions sound expensive.
Here’s a secret.
When you split the costs of a luxury villa rental amongst multiple families, it’s often cheaper per person than booking everyone hotel rooms. Not to mention the experience is so much better.
Take these tips into consideration when it comes to budgeting for your family’s next reunion:
Splitting the bill.
Splitting the cost of the villa rental evenly between families will help make that large villa affordable. When split between 5-6 families, even larger villas come down to a very reasonable rate.
Hiring a private chef.
Did you know that you can hire private chefs to cook for your family while on vacation? Not only will this save you tons of money by not eating out every night, but think of all the delicious meals your family can enjoy together.
Transportation.
If you’re flying into a major airport nearby your villa, look into shuttle services or renting a van for your families to share transport costs.
Booking ASAP.
The best villa rentals book quickly, especially during peak seasons. To ensure you secure the best villa for your family’s next reunion, try to book your vacation 1 – 2 years in advance.
Wrapping It Up
Gathering your entire family in one place for a weekend (or week) of fun and relaxation is one of the best gifts you can give your family.
With a destination reunion, you take everyone out of their comfort zone and make them appreciate each other.
To recap on how to plan a stress-free and memorable destination reunion:
- Pick a destination with nearby major airports, year-round good weather and activities for all ages.
- Book a private villa rental that fits all of your families together in one place.
- Plan activities that everyone can enjoy together and some alone.
- Split the costs amongst multiple families to save money and book early to secure the best villa rentals.
The families that take the time to plan one destination reunion will almost always plan another. There’s nothing better than bringing three or four generations together in one unforgettable destination.
Say goodbye to boring backyard reunions. Plan your destination reunion today!
