Large Villa Holidays: pressure off, party on!
- By Simpson Travel
- 30 Apr 2026
- Where to go
We get it. Being the group holiday organiser for a large party can suck up hours in research. It’s no joke trying to find the best accommodation for multiple families with kids, or maybe a group of adult friends needing a villa with a pool, walkable restaurants, direct flights and a great bedroom/bathroom ratio… and that’s before you even start thinking about which European destinations are best for groups! But don't stress, help is here.
Hacks for Group Trip Organisers
Stuck with the job of organiser? At Simpson Travel, we literally do this for a living, so however complex and demanding your party dynamics are, we’ll get on the case to find your group holiday accommodation for 8, 10, 12, 14, 16, 18 or even more in Greece, Turkey, Mallorca, Italy, France, Corsica or Portugal. Our team have visited every single one of our villas, and we're all about the details. This means we can tell you everything you need to know about the layout, down to the sizes of the beds and the number of pool loungers, so even that super-picky person – because every group has one – will thank you for doing a brilliant job. And don't forget that booking a package with a tour operator also means you get full financial protection, unlike many villa-only sites or booking platforms.
Time that Works for You
Prefer to research online after hours? Our website has a ton of helpful filters so you can quickly generate a useful shortlist of villas for your group in one place instead of having a hundred tabs open from different sites – just enter the number of guests travelling and then refine the results using the ‘facilities’ filters on the left-hand side. Pick a destination and dates, or leave it open and see what matches your criteria. You can also use our Dreamcrafter feature to search villas by image – a great way to find inspiration.
Local Concierges to Take Care of You
In addition to taking the pain out of finding that perfect large villa, you also get the services of our own local concierges to organise everything from boat hire and beach recommendations to booking the best local restaurants. And if you want to take the whole holiday up a notch or two, we’ll be happy to find you that private chef or book a massage or yoga session at your villa: no chatbots, just real, friendly, knowledgeable people, and all part of the Simpson Travel service.
Tips to Get you Started
The possibilities for large villa holidays are practically endless, but to get you started, we’ve listed some typical scenarios, checklists and group villa recommendations below. Not quite what you’re looking for? Get in touch for some free, expert advice on the fine art of choosing the best villas for groups.
Scenario 1: The big group get together at a villa.
Girlfriends, golfers, couples, uni mates or old school friends: whatever the original connection, you’ve been friends for ever and this is the one week of the year you always make time for. The stakes are high, and the wish list is long.
Villa Essentials
- Realistic space for a large group – no sofa beds or bunks please, we're all adults
- A private pool – this time is yours, no one else’s
- Direct flights included – because a week is already too short
Nice to Have
- Gym or gym equipment
- Visiting spa service
- Pool lighting for evenings in
- Walkability – the trending holiday luxury in 2026
Recommended Villas for Big Groups
Scenario 2: A villa (or villas) for multiple families together
Company for the kids, freedom for the adults, a social life without going out. You met when the kids were tiny, and going away on an annual villa holiday together just gets better and better each year. The destination is less important than the accommodation, and the photos make for priceless memories of fleeting years.
Villa Essentials
- Large, safe garden – or a beach very nearby
- Private pool – it’s just not a villa holiday without one (choose gated if you have young kids)
- A proper kitchen – eating in is part of the fun
- Welcome pack – or upgrade to a pre-arrival supermarket delivery
Nice to Have
- Annexe/den for older kids
- Outdoor kitchen
- Home cinema
- Table tennis
Recommended Villas for Multiple Family Groups
Scenario 3: Big luxury villa for a special occasion
Multi-generation mix? Perhaps. Memorable? Most definitely. Whether it’s a milestone birthday, a wedding anniversary or whatever you feel like celebrating, we can find you the right villa and luxe things up with a private chef, villa wine tastings, boat trips or even a photographer in certain destinations to capture the special moments. And if you choose one of our luxury Signature collection villas, you also get the dedicated service of our groups organiser: pressure off, party on!
Villa Essentials
- All bedrooms en-suite – max privacy, no loo queues
- A private pool – a focal point for the party
- Space to entertain – a dining table that can accommodate you all
- Contemporary luxury or grand design – to match the sense of occasion
- Flights and car-hire included – let us take care of everything
Nice to Have
- Private chef
- Breakfast delivery
- Tennis court
Recommended Villas for Group Celebrations and Occasions
Not found the one yet? See our full collection of large villas for groups
