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Large villas in Italy

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Our collection of large villas in Italy sleep up to 30 guests in country estates, historic palaces, castles, heritage properties and large stone-built farmhouses. Whether you are arranging a family reunion in Italy, or simply travelling in a large group, our handpicked villas accommodate you in style.

This curated selection of large villas in Italy includes properties ideal for multi-generational travel. If you are travelling with parents or grandparents who would like the added privacy of their own entrance or outbuilding, this collection includes several options (or ask our dedicated villa specialists for advice). Older teenagers also enjoy staying in our large villas: they provide the freedom of large grounds or annexes — sometimes both.

All our large villas in Italy have private swimming pools. Most of these villas for large groups come with air-conditioning, either in bedrooms or throughout the property. You will enjoy spacious, luxurious interiors and bedrooms with ensuite bathrooms (or, generally, one bathroom per bedroom). Panoramic terraces and well-tended gardens are popular spots for morning and evening downtime.

Our large villas in Tuscany include properties with private tennis courts and with heated pools or hot tubs, such as this 900-acre wine and olive oil estate close to Rufina. Among our large villas in Umbria are the former townhouse residence of neoclassical sculptor Antonio Canova (1757–1822) and a grand 17th-century villa near Perugia, where daily breakfast and maid service is included in the price.

Everyone who stays in our large villas in Italy has free access to our award-winning concierge service. These local travel experts can help you arrange something extra special for your large group or family reunion. Popular large group activities include woodland truffle hunting, ballooning over Tuscany and group cookery classes in your villa kitchen. Our concierges can also arrange a private chef to come to your villa and cook for a special occasion — or all week, if you wish.

If you are searching for a large villa to get married, see our collection of wedding villas in Italy. We can arrange staff and chefs to make your special day run smoothly; connect you with experienced wedding planners; and arrange unique tours or Tuscan wine tastings to keep your guests entertained throughout their stay. Contact us with any questions.

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Showing: 38 villas

Villas near Pisa and Lucca - Tuscany

Villa Dasya

Rental options (size of party):
Villa Dasya | 7 Bed Luxury Villa with Pool | Pisa & Lucca - A shaded terrace for al fresco dining.
Villa Dasya - Plenty of seating on the shaded terrance
Villa Dasya - On the same level as the ground floor; paved terrace with two outside shaded dining areas
Villas near Pisa and Lucca - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

Stunning home on the edge of a village with a private heated pool. Beautiful garden, lots of shaded living areas, wonderful views of the village. A/C bedrooms, sophisticated living rooms, fantastic kitchen.

Weekly prices
From
To
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€ 10,269
€ 13,792
$ 11,147
$ 14,970
£ 8,777
£ 11,788
44 Guest reviews
"Featured in the Brides magazine"
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Villas near Todi - Umbria

Santi Terzi

Rental options (size of party):

Special rates for July and August

Santi Terzi - Santi Terzi has emerged as a magnificent yet cheerful private villa in with the original architectural elements
Santi Terzi - The sun drenched pool terrace
Santi Terzi - Second floor one of two large sitting room with a fireplaces
Villas near Todi - Umbria

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

Renovated period palazzo with private heated pool in the medieval hill-town of San Gemini. A/C bedrooms with views & outdoor dining loggia. Enchanting stroll along cobbled streets to shops & restaurants. Rental option with cook available.

Weekly prices
From
To
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€ 3,660
€ 7,196
$ 3,973
$ 7,811
£ 3,128
£ 6,150
49 Guest reviews
"Featured in The Richmond Magazine"
View full details

Special rates for July and August

Santi Terzi (x 14 people) with Staff and Cook - This stunning period palazzo, once home to Canova, the neoclassical sculptor, is set in San Gemini.
Santi Terzi (x 14 people) with Staff and Cook - The sun drenched pool terrace
Santi Terzi (x 14 people) with Staff and Cook - Staff preparing meals at the villa.
Villas near Todi - Umbria

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

This rental option for Santi Terzi includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week. The cost of food & drinks is not included.

Weekly prices
From
To
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€ 5,792
€ 9,642
$ 6,286
$ 10,467
£ 4,950
£ 8,241
49 Guest reviews
"Featured in The Richmond Magazine"
View full details

Special rates for July and August

Santi Terzi - Santi Terzi has emerged as a magnificent yet cheerful private villa in with the original architectural elements
Santi Terzi - The sun drenched pool terrace
Santi Terzi - Second floor one of two large sitting room with a fireplaces
Villas near Todi - Umbria

SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

Renovated period palazzo with private heated pool in the medieval hill-town of San Gemini. A/C bedrooms with views & outdoor dining loggia. Enchanting stroll along cobbled streets to shops & restaurants. Rental option with cook available.

Weekly prices
From
To
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€ 4,210
€ 8,291
$ 4,570
$ 9,000
£ 3,598
£ 7,086
49 Guest reviews
"Featured in The Richmond Magazine"
View full details

Special rates for July and August

Santi Terzi (x 20 people) with Staff and Cook - This stunning period palazzo, once home to Canova, the neoclassical sculptor, is set in San Gemini.
Santi Terzi (x 20 people) with Staff and Cook
Santi Terzi (x 20 people) with Staff and Cook
Villas near Todi - Umbria

SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

This rental option for Santi Terzi includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week. The cost of food & drinks is not included. Rental option with chef & all-inclusive wine available.

Weekly prices
From
To
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€ 7,161
€ 11,679
$ 7,773
$ 12,677
£ 6,120
£ 9,982
49 Guest reviews
"Featured in The Richmond Magazine"
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Villas in Chianti - Tuscany

Tizzano

Rental options (size of party):
Tizzano - Ideally arranged seating for relaxing outdoors at all hours.
Tizzano - The extensive use of glass gives the feeling of open-planned spaces in the Lemon House.
Villas in Chianti - Tuscany

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and Chef service for 6 breakfast is also included in the price.

Weekly prices
From
To
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€ 7,519
€ 11,702
$ 8,162
$ 12,702
£ 6,427
£ 10,002
40 Guest reviews
View full details
Tizzano - Ideally arranged seating for relaxing outdoors at all hours.
Tizzano - The extensive use of glass gives the feeling of open-planned spaces in the Lemon House.
Villas in Chianti - Tuscany

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 8

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and chef service for 6 breakfast included in the price.

Weekly prices
From
To
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€ 8,099
€ 12,602
$ 8,791
$ 13,679
£ 6,922
£ 10,771
40 Guest reviews
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Villas near Siena - Tuscany

La Piana

Rental options (size of party):
La Piana - This beautiful stone farmhouse is set on one of the many magical hill tops that dot the stunning countryside just south of the city of Siena.
La Piana - A beautiful retreat with views over the rolling Tuscan countryside.
La Piana
Villas near Siena - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Picturesque stone farmhouse on a hill top with sweeping views of the countryside near to Siena. Private pool & pool house. modern outside lounging area and air conditioned bedrooms

Weekly prices
From
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€ 6,377
€ 10,042
$ 6,922
$ 10,900
£ 5,450
£ 8,583
63 Guest reviews
View full details
La Piana - This beautiful stone farmhouse is set on one of the many magical hill tops that dot the stunning countryside just south of the city of Siena.
La Piana - A beautiful retreat with views over the rolling Tuscan countryside.
La Piana
Villas near Siena - Tuscany

SLEEPING: 18 - BEDROOMS: 11 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Picturesque stone farmhouse on a hill top with sweeping views of the countryside near to Siena. Private pool & pool house. modern outside lounging area and air conditioned bedrooms

Weekly prices
From
To
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€ 7,594
€ 12,389
$ 8,243
$ 13,448
£ 6,490
£ 10,589
63 Guest reviews
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Villas near San Gimignano - Tuscany

Casa Tara

Rental options (size of party):
Casa Tara - The private swimming pool, 6 x 12m/19 x 38 feet is set on a lower terrace.
Casa Tara - Main house dining room, kitchen to the right.
Casa Tara - Guest house, views from the dining loggia.
Villas near San Gimignano - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

Weekly prices
From
To
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€ 6,107
€ 9,423
$ 6,629
$ 10,228
£ 5,220
£ 8,054
32 Guest reviews
View full details
Casa Tara - The private swimming pool, 6 x 12m/19 x 38 feet is set on a lower terrace.
Casa Tara - Main house dining room, kitchen to the right.
Casa Tara - Guest house, views from the dining loggia.
Villas near San Gimignano - Tuscany

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 8

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

Weekly prices
From
To
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€ 7,634
€ 11,779
$ 8,286
$ 12,786
£ 6,525
£ 10,068
32 Guest reviews
View full details

Villas in Chianti - Tuscany

Podere Brogi

Rental options (size of party):
Podere Brogi - The 5.5 x 17m/18 x 54 feet swimming pool is fully lit for a refreshing evening swim.
Podere Brogi - Dine with a view at Podere Brogi
Podere Brogi - Beautiful air conditioned bedrooms
Villas in Chianti - Tuscany

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Fully air conditioned luxury villa on the edge of the Chianti with a large private heated pool, en suite bathrooms, professional kitchen, fantastic outside living & dining areas. Superbly managed.

Weekly prices
From
To
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€ 5,313
€ 9,347
$ 5,767
$ 10,146
£ 4,541
£ 7,989
138 Guest reviews
"Featured in the Connoisseur Circle magazine"
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Podere Brogi - The 5.5 x 17m/18 x 54 feet swimming pool is fully lit for a refreshing evening swim.
Podere Brogi - Dine with a view at Podere Brogi
Podere Brogi - Beautiful air conditioned bedrooms
Villas in Chianti - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Fully air conditioned luxury villa on the edge of the Chianti with a large private heated pool, en suite bathrooms, professional kitchen, fantastic outside living & dining areas. Superbly managed.

Weekly prices
From
To
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€ 6,666
€ 11,665
$ 7,236
$ 12,662
£ 5,698
£ 9,970
138 Guest reviews
"Featured in the Connoisseur Circle magazine"
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Villas near Montepulciano - Tuscany

Villa Astori

Rental options (size of party):
Villa Astori - Villa Astori, Poggio Cantarello, near Montepulciano, Tuscany.
Villa Astori - A pretty outdoor dining pergola with views of the Tuscan rolling hills.
Villa Astori - Relaxing by the pool.
Villas near Montepulciano - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

Weekly prices
From
To
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€ 4,966
€ 8,444
$ 5,390
$ 9,165
£ 4,244
£ 7,217
18 Guest reviews
View full details
Villa Astori - Villa Astori, Poggio Cantarello, near Montepulciano, Tuscany.
Villa Astori - A pretty outdoor dining pergola with views of the Tuscan rolling hills.
Villa Astori - Relaxing by the pool.
Villas near Montepulciano - Tuscany

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

Weekly prices
From
To
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€ 5,596
€ 9,556
$ 6,075
$ 10,373
£ 4,783
£ 8,168
18 Guest reviews
View full details
Villa Astori - Villa Astori, Poggio Cantarello, near Montepulciano, Tuscany.
Villa Astori - A pretty outdoor dining pergola with views of the Tuscan rolling hills.
Villa Astori - Relaxing by the pool.
Villas near Montepulciano - Tuscany

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 10

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

Weekly prices
From
To
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€ 6,603
€ 11,323
$ 7,167
$ 12,291
£ 5,644
£ 9,678
18 Guest reviews
View full details

Villas near Montepulciano - Tuscany

Podere Casalfava

Rental options (size of party):
Podere Casalfava - The nearest restaurant, La Laterna, is a short walk down the road; the nearest shops and a thermal spa - are in Sarteano
Podere Casalfava - Beautiful archway leads into the dining area.
Villas near Montepulciano - Tuscany

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Fully air-conditioned villa
  • Internet connection
  • Private pool

Luxury stone farmhouse in Tuscany with a private swimming pool just outside a village. Air-con bedrooms & ensuite bathrooms. Beautiful gardens with unspoilt views. Within walking distance to great restaurants & the village Sarteano.

Weekly prices
From
To
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€ 4,825
€ 9,708
$ 5,237
$ 10,538
£ 4,124
£ 8,298
62 Guest reviews
View full details
Podere Casalfava - The nearest restaurant, La Laterna, is a short walk down the road; the nearest shops and a thermal spa - are in Sarteano
Podere Casalfava - Beautiful archway leads into the dining area.
Villas near Montepulciano - Tuscany

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Fully air-conditioned villa
  • Internet connection
  • Private pool

Luxury stone farmhouse in Tuscany with a private swimming pool just outside a village. Air-con bedrooms & ensuite bathrooms. Beautiful gardens with unspoilt views. Within walking distance to great restaurants & the village Sarteano.

Weekly prices
From
To
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€ 5,492
€ 11,014
$ 5,962
$ 11,955
£ 4,694
£ 9,413
62 Guest reviews
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Villas near Cortona - Umbria

Le Gorgacce

Rental options (size of party):
Le Gorgacce | 7 Bed Luxury Villa with Pool | Cortona - Le Gorgacce, in the hills west of Citta di Castello. Umbria.
Le Gorgacce - Another view of the pool house.
Le Gorgacce - Al fresco dining, positioned for the views.
Villas near Cortona - Umbria

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

Charming stone farmhouse & guest house with a large pool. Air-conditioned bedrooms in the main house, shaded living areas, sauna, gym. Private location and peaceful garden with well-kept lawns and impeccable views.

Weekly prices
From
To
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€ 4,629
€ 6,822
$ 5,025
$ 7,405
£ 3,957
£ 5,831
35 Guest reviews
View full details
Le Gorgacce | 7 Bed Luxury Villa with Pool | Cortona - Le Gorgacce, in the hills west of Citta di Castello. Umbria.
Le Gorgacce - Another view of the pool house.
Le Gorgacce - Al fresco dining, positioned for the views.
Villas near Cortona - Umbria

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 8

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

Charming stone farmhouse & guest house with a large pool. Air-conditioned bedrooms in the main house, shaded living areas, sauna, gym. Private location and peaceful garden with well-kept lawns and impeccable views.

Weekly prices
From
To
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€ 5,787
€ 8,528
$ 6,281
$ 9,257
£ 4,946
£ 7,289
35 Guest reviews
View full details

Villas in Chianti - Tuscany

Montesassi (x 10 people)

Rental options (size of party):
Montesassi - Stunning views of the Chianti.
Montesassi - The private swimming pool, 7 x 15 meters/22 x 48 feet.
Villas in Chianti - Tuscany

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Converted 400-year-old farmhouse on a Chianti hilltop with staff & cook. Private pool, tennis court & A/C bedrooms with en-suite bathrooms. Plenty of outdoor living & dining areas. Breakfast & dinner service included in the rental price. 

Weekly prices
From
To
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€ 7,220
€ 10,645
$ 7,837
$ 11,555
£ 6,171
£ 9,098
67 Guest reviews
View full details

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