Whether you thrive best in the great outdoors or would rather spend your downtime at your favourite art museum, Tuscany provides an easy balance for luxury group getaways. The region offers something for everyone, with its perfect blend of stunning scenery, rich cultural heritage and delicious cuisine. Tuscany is ideal for young families and endlessly romantic for grand reunions, special occasions and weddings.
With over 30 years of experience, Tuscany Now & More handpick the finest villa rentals in Tuscany for carefree family travel. Our large luxury villas in Tuscany are perfect for extended family vacations and can host up to 30 people. They include grand estates, historic palaces, and exquisite farmhouse conversions.
Perfect for reunions or getaways with friends, this special collection guarantees that everyone enjoys privacy, peace and panoramic views. Here is our round-up of 5 of our favourite villas in Tuscany for large group and family vacations:
Our Top 5 Villas for Luxury Group Getaways in Tuscany:
Santa Dieci
Santa Dieci is an enchanting one-thousand-year-old tower near Siena that is ideal for large groups. The villa offers a perfect blend of history and modern sophistication, featuring a private swimming pool, hot tub, air-conditioned bedrooms, and a large professional kitchen. The villa terrace offers stunning views, providing ample space for group gatherings.
Our favourite features:
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Stunning views of Siena
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Set on a private wine estate
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Helpful owners who offer a fantastic local service that our clients rave about
Helpful to know:
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Up to 10 guests
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Can be rented fully-staffed with an in-villa chef
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3km from the centre of Siena and heritage sites
I Giullari
I Giullari is a beautifully renovated farmhouse. It is ideal for large groups looking to discover Florence, which is easily accessible by foot or public transportation. A private heated swimming pool, air-conditioned bedrooms and ensuite bathrooms make this an extremely comfortable base for friends and families who prefer everything they need within walking distance.
Our favourite features:
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The heated infinity pool with stunning views
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Walk to a local trattoria for lunch
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Fantastic base for walking into Florence
Helpful to know:
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Up to 18 guests
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Fully air-conditioned
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3km from Porta Romana, Florence
Poggio ai Grilli
Poggio ai Grilli is a grand Tuscan farmhouse set on a gloriously peaceful and private organic estate that produces Extra-Virgin Olive Oil, IGT wines and more. Fully staffed with a skilled local chef, larger groups can focus on relaxing, exploring the surrounding Tuscan hills and venturing into Pisa and Lucca. With a large private swimming pool and tennis court, there is plenty going on at the villa to keep everyone entertained.
Our favourite features:
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Private tennis court
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Fenced private pool for young families
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Restaurants within walking distance
Helpful to know:
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Up to 14 guests
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Fully staffed with chef services including six breakfasts and six dinners
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A 30-minute drive to the Leaning Tower of Pisa
Spini Bianchi
A haven for groups wanting to explore the Tuscan Coast, Spini Bianchi is an idyllic luxury villa with a private infinity swimming pool and tennis court. The villa is situated in complete seclusion, enjoying unforgettable views of the coastline towards the island of Giglio. The alfresco dining areas promise dreamy alfresco dinners and wine tastings. And there are beautiful beaches and coves on the doorstep waiting to be explored.
Our favourite features:
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Private tennis court
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Mesmerising coastal views
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The infinity edge pool and Mediterranean garden
Helpful to know:
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Up to 8 guests
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Monte Argentario
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6km to the fishing village of Santo Stefano
Podere Casalfava
Situated on a tranquil hillside near Sarteano, Podere Casalfava is perfect for large groups wanting to unwind and explore the Val d’Orcia and Val di Chiana in equal measure. Spend most of your time outside by your private swimming pool, while your children play on the sprawling lawns. The owners work with a fantastic local chef who can prepare meals at the villa! The traditional wood-burning oven in the summer kitchen is made for Bistecca alla Fiorentina dinners.
Our favourite features:
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The summer kitchen for al fresco dining and Bistecca dinners
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Spacious interiors with classic Tuscan features
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Tranquil setting with thermal spa, restaurants and shops within walking distance
Helpful to know:
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Up to 14 guests
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Large private swimming pool
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2km to the pretty village of Sarteano
Book your luxury group vacation rental with Tuscany Now & More
Feeling inspired to plan your large group vacation in Tuscany? Contact our Villa Specialists to find out how we can make your dream luxury family vacation in Tuscany a reality.
You can elevate your experience of luxury travel in Tuscany even further with our complimentary Concierge Service. We can arrange exclusive experiences and bespoke services, like dinners prepared by an in-villa chef and additional housekeeping.