Large Group Holidays in September
- By Simpson Travel
- 07 Aug 2026
- Where to go
Why September is the sweet spot for a villa holiday in Greece, Turkey, Portugal, Mallorca, Italy and France
There’s a quiet magic to September in southern Europe. The intensity of high summer softens, the pace slows and the landscapes ripen into the bounty of harvest time. Sun-warmed seas still invite morning swims, days are cool enough to walk a little or explore the sights and evenings are made for lingering around the table beneath a canopy of stars.
For families bringing generations together, groups of friends celebrating a milestone, or those simply seeking time to reconnect, September offers one of the most rewarding times to escape. School holidays mean bigger properties are booked up very early in July and August, but the turn of the season means better availability in September for luxury villas with room for 6, 8, 10 or even twenty. This is time for you and your favourite people, and September provides an idyllic canvas to paint new memories upon.
Where to go on holiday with a large group in September
While autumn begins to make itself known at home, southern Europe continues to bask in late-summer warmth. Across Greece, Spain, Portugal and beyond, the sea remains wonderfully warm, days are comfortably sunny, and the atmosphere feels altogether more authentic once the peak-season crowds have departed. Corsica’s incredible mountain scenery becomes more attractive for walkers, Puglia’s coastal crowds thin out and Mallorca enjoys prime golfing weather for its 20+ courses.
GR20 walking trail in Corsica
Golf in The Algarve
Beaches are quieter, village squares regain their local charm, and there's space to savour every moment—whether that means exploring hidden coves, browsing colourful markets or simply settling into a favourite taverna for an unhurried lunch.
Why a villa holiday is the best solution for groups
There's something special about sharing a villa with the people who matter most. Unlike a hotel, where everyone retreats to separate rooms at the end of the day, a private villa creates space for holidays to unfold naturally. Mornings begin over coffee on the terrace, afternoons revolve around the pool, and evenings are spent gathered around one table, sharing local food, stories and laughter. It's these unplanned moments that often become the memories everyone talks about long after the holiday ends.
This is also prime time for pre-schoolers, as the gentler temperatures are easier on tender young skin, and a less frantic pace means families with young children can take their time to work around naps, meal times as needed. At selected villas we also offer a complimentary infant pack so you can travel a little lighter safer in the knowledge that everything you need will be there when you arrive.
Whether you're travelling with grandparents, cousins, lifelong friends or several families together, a thoughtfully chosen villa offers the freedom to holiday at your own pace, with generous living spaces, private pools, beautiful gardens and room for everyone to feel at home.
Mirabello Bay House, Crete
Mirabello Bay House, Crete
This is a town best experienced on foot, preferably without a plan. Mornings begin with coffee by the water, fishing boats nudging gently against the quay as the catch of the day flashes silver in the early sunlight. As the heat rises, the shaded backstreets come alive; stone stairways lead to elegant neoclassical homes and inviting little shops stocked with hand-finished linens, ceramics, herbs and oils. When evening comes, the harbour takes on a low-key glamour – candles flicker, glasses clink and menus tempt with a rather more sophisticated choice of dishes than you might expect.
Five idyllic villa destinations for a holiday in September
Mallorca villas in September
By September, Mallorca reveals a calmer side. Its beautiful coastline remains inviting for swimming, while the island's elegant villages, vineyards and mountain landscapes become even more enjoyable to explore. Whether you choose a countryside retreat or a villa overlooking the sea, Mallorca effortlessly combines sophistication with laid-back Mediterranean living.
Mallorca Villas
Crete villas in September
Crete rewards those who visit later in the season. Golden beaches, crystal-clear waters and warm Cretan hospitality remain as welcoming as ever, while quieter roads and villages invite deeper exploration. From archaeological treasures to traditional tavernas serving seasonal dishes, it's an island that offers something for every generation.
Crete Villas
The Algarve villas in September
With its dramatic coastline, exceptional beaches and relaxed atmosphere, the Algarve continues to enjoy glorious weather throughout September. Spacious villas, world-class golf, fresh seafood and spectacular sunsets make it an ideal choice for larger groups looking to combine relaxation with gentle adventure.
Portugal Villas
Turkey villas in September
The sun sets a little earlier in September, lending a special magic to Kalkan’s rooftop restaurants, though you may find the starlit evenings even more of a treat when you savour them from your own villa terrace. The Turquoise Coast has a vast wealth of archaeological sites to discover, from sunken ruins to an ancient city half buried in the sand behind one of Europe’s most spectacular beaches.
Turkey Villas
Italy villas in September
Food is always front and centre on an Italy villa holiday, but the month of September sees a mountain of fresh produce arriving in shops and on local market stalls, plus quieter restaurants so you don’t feel you have to plan your lunch booking days in advance. Food festivals celebrate the season and the abundance of nature.
Italy Villas
The Joy of Travelling Together
Bringing a large group together naturally requires a little more planning, but it also creates the kind of holidays that stay with you for years. After all, the best holidays aren't simply about where you go – they're about who you share them with.
Choosing a villa designed for larger parties means everyone can enjoy both shared spaces and quiet corners to themselves. When planning, it's worth considering:
- Spacious indoor and outdoor dining areas
- Comfortable bedroom layouts across multiple generations
- A private swimming pool
- Air conditioning throughout the villa
- Easy access to beaches, restaurants and local villages
- Parking if you're planning to explore by car
The best villas balance togetherness with privacy, allowing every guest to holiday in their own way.
September holidays simplified
With more choice available across our collection, finding the right villa for a larger group often becomes easier than during the height of summer. Flight availability is often easier to find, so you can choose a route that suits you and your party.
Our team specialises in matching guests with villas that suit the unique needs of every group – whether that's celebrating a special occasion, travelling with young children or finding a property where three generations can holiday comfortably together. From your first enquiry to your return home, we're here to ensure every detail is thoughtfully taken care of.
