Holiday Homes for Groups in Tuscany

Tuscany is the Italian region of genuine flavors and good living, a suitable place to spend a holiday with close friends or to celebrate some important date with family members. In this space there are holiday homes suitable for hosting large groups, consisting of more than 14 people, with a private swimming pool and large outdoor spaces, where children can play freely, to spend peaceful days surrounded by all possible comforts and affection of loved ones. The holiday homes dedicated to groups have been meticulously selected by us for the attention to detail, for the organized spaces and for the gardens scented with aromatic herbs where the harmony between your desire for well-being and the place becomes a real magic. Finding yourself at the table under a romantic pergola with delicate dishes and good red wine, while the days pass slowly and the sun illuminates the vineyards and olive groves, is a dream within reach. To make it come true, we have tested and checked all the holiday homes for you as well as we have taken care of the relationship with their owners so that every service we offer is the best possible.

January 2026
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19 Results:

Fattoria Antica
Holiday Homes for Groups
10 Apartments, 44+8 Sleeps, 22 Bedrooms, 17 Bathrooms, Internet connection, Private pool, Fenced, Pets
From €11,900.00
Welcome to Fattoria Antica: the ideal setting for your Tuscan wedding. This exquisite wedding venue welcomes up to 52 guests, blending the romantic charm of the Tuscan countryside with refined elegance for an unforgettable celebration. Set amidst the rolling hills of Tuscany, Fattoria Antica is a beautifully restored country estate that perfectly blends rustic charm with modern comfort. Surrounded by vineyards, olive groves, and centuries-old cypress trees, the property offers a peaceful atmosphere where guests can truly relax and experience the authentic Tuscan lifestyle. The estate features several charming villas and apartments of various sizes, ideal for couples, families, or groups of friends. Each accommodation is tastefully furnished in traditional Tuscan style, with terracotta floors, wooden beams, and warm colors that reflect the region’s unique character. Guests can enjoy private gardens, terraces with breathtaking views, and a large swimming pool overlooking the countryside - the perfect place to unwind with a glass of local wine at sunset. All accommodations are equipped with modern amenities to ensure a comfortable and relaxing stay, while still preserving the genuine spirit of rural Tuscany. Whether you are planning a romantic getaway, a family holiday, or a special celebration, Fattoria Antica offers an unforgettable setting for your stay - a place where history, nature, and hospitality come together in perfect harmony.
Podere Casentino
Holiday Homes for Groups
40+25 Sleeps, 22 Bedrooms, 19 Bathrooms, Internet connection, Private pool, Fenced, Pets
From €4,200.00
Large typical Tuscan farmhouse completely in stone for exclusive use, in a splendid panoramic position surrounded by unspoiled nature, 400,000 square meters of enclosed land, WiFi Internet, private swimming pool 8x16 m., SPA wellness area (on request, extra to pay), barbecue area, wood oven, park games for children, farm animals, a dream for large families with children! from 40 to 65 pax (49 adults and 16 children under 12 y.o.). CIN: IT051004B5XC2F68Z5National Tourism Accommodation Code
Casale Cortona
Holiday Homes for Groups
18+0 Sleeps, 10 Bedrooms, 8 Bathrooms, Internet connection, Air Conditioning, Private pool, Fenced, Pets
From €2,950.00
Large natural stone cottage for 18 people in Cortona, in an ideal location in the heart of Tuscany, spacious and child-friendly facility, lawns, swimming pool, barbecue area, table tennis, shopping opportunities in the immediate vicinity. CIN: IT051017B5GL35EP65  
Villa della Rosa
Holiday Homes for Groups
18+3 Sleeps, 9 Bedrooms, 11 Bathrooms, Internet connection, Air Conditioning, Private pool, Fenced
From €4,330.00
A dreamy environment awaits you in this Tuscany holiday home suitable for large groups and families up to 21 people (max. 17 adults + 4 children under 12 years), 9 bedrooms, 10 bathrooms, extra-large private pool with enclosed children's pool, enchanting panoramic and isolated position in the countryside, barbecue area, pizza oven, common rooms, satellite TV and WiFi Internet meet the highest demands. Main house 320 sq m. Dependence with common spaces 120 sq m.CIN: IT051004B5L3ZZE4C8