Fully staffed and catered villas with chefs in Italy

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At our staffed and catered villas in Italy, you are in the hands of experts. You concentrate on enjoying yourself — relaxing by your private swimming pool or taking daytrips to some of Italy’s prettiest towns and villages — while our chef, maid and other staff look after you throughout your stay. Our villas with staff and cook sleep from two people to 30.

Each of our staffed villas with chef in Tuscany and Umbria has air-conditioning, either in bedrooms or throughout the villa. Even on warm summer nights, you are sure to get a good night’s sleep.

You will rise refreshed to enjoy breakfast prepared for you. Staff serve breakfast indoors or on your private terrace. Evening meals are cooked by local chefs following the traditional recipes of Tuscany and Umbria. See the individual villa listings, below, for details of exactly what your catered villa with chef includes. The cost of ingredients and wine is not generally included in the villa rental price.

Like every Tuscany Now & More villa rental, you also benefit from free use of our award-winning concierge service. Our experienced concierges are available from the minute you book to help tailor a trip around you and your travelling companions. They can arrange a wine tasting in your villa kitchen, an early morning truffle hunt or just find you a table at the best local restaurant on your chef’s evening off. Our concierges can order shopping delivered to your villa on arrival. We also have dedicated ground staff in Italy and a 24-hour emergency number.

Our special collection of fully staffed villas in Italy includes a range of holiday rentals in Tuscany and Umbria. Each catered villa listed below is exclusive to Tuscany Now & More, including a wine and olive oil estate near Rufina, a restored Medici villa overlooking Florence and original stone farmhouses of all sizes. Many also make unforgettable wedding venues, for anyone looking to get married in Italy.

If you want to explore even deeper into the regional food of Italy, we also offer a select few cooking vacations in Tuscany, with private cooking lessons, culinary excursions and wine tasting included in the villa rental price.

Condé Nast Traveller 2023 Award
Showing: 38 villas
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Showing: 38 villas

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
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€ 4,629
€ 6,822
$ 4,989
$ 7,352
£ 3,991
£ 5,881

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
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€ 5,787
€ 8,528
$ 6,236
$ 9,190
£ 4,989
£ 7,352

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
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€ 7,220
€ 10,645
$ 7,780
$ 11,471
£ 6,224
£ 9,177

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Hot tub

Classic stone farmhouse in the Val d’Orcia with panoramic views of Pienza. Fully A/C, spacious open-plan living areas with ensuite bathrooms. 12m infinity pool, hot tub & dining terrace.

Weekly prices
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€ 7,384
€ 10,548
$ 7,957
$ 11,367
£ 6,365
£ 9,093

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Tastefully renovated house with a private heated pool at the edge of a pretty hilltop town. Contemporary interiors, walled garden, air-con bedrooms. Walk to the main square, bars, shops, & restaurants.

Weekly prices
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€ 2,000
€ 4,473
$ 2,155
$ 4,820
£ 1,724
£ 3,856

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Tastefully renovated house with a private heated pool at the edge of a pretty hilltop town. Contemporary interiors, walled garden, air-con bedrooms. Walk to the main square, bars, shops, & restaurants.

Weekly prices
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€ 2,194
€ 4,855
$ 2,364
$ 5,232
£ 1,891
£ 4,186

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

This option includes chef services for 3 dinners and 6 breakfasts, ingredients not included. Renovated house with a private heated pool and air-con bedrooms at the edge of a pretty hilltop town. Walk to the main square, bars, shops, & restaurants.

Weekly prices
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€ 3,051
€ 6,112
$ 3,288
$ 6,586
£ 2,630
£ 5,269

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Hilltop stone villa with private heated pool, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
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€ 2,998
€ 4,916
$ 3,230
$ 5,298
£ 2,584
£ 4,238

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Hilltop stone villa with staff & cook, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Private heated pool & panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
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€ 3,195
€ 5,114
$ 3,443
$ 5,510
£ 2,754
£ 4,408

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

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

Hilltop stone villa with private heated pool, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
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€ 3,357
€ 5,563
$ 3,618
$ 5,995
£ 2,894
£ 4,796

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

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

Hilltop stone villa with staff & cook, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Private heated pool & panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany. 

Weekly prices
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€ 3,555
€ 5,761
$ 3,831
$ 6,208
£ 3,065
£ 4,967
Rental options (size of party):

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Fully-staffed stone villa near Rome with 360° views of Tuscia countryside. Fully A/C, bright contemporary interiors and ensuite bathrooms. 13m infinity pool, stunning terraced garden.

Weekly prices
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€ 3,147
€ 5,192
$ 3,391
$ 5,595
£ 2,713
£ 4,476

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable villa with a private pool, near San Gemini. Tastefully decorated. Air-conditioned bedrooms. Ensuite bathrooms. Beautiful garden, loggias, views. Large pool, Hike to village.

Weekly prices
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€ 1,318
€ 2,812
$ 1,420
$ 3,030
£ 1,136
£ 2,424

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at l’Olmo includes a talented local cook that shall prepare your evening meals. Breakfast is also included and prepared by the maid. Please note that food & wine are not included.

Weekly prices
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€ 2,793
€ 4,288
$ 3,010
$ 4,620
£ 2,408
£ 3,696

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable villa with a private pool, near San Gemini. Tastefully decorated. Air-conditioned bedrooms. Ensuite bathrooms. Beautiful garden, loggias, views. Large pool, Hike to village.

Weekly prices
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€ 1,465
€ 3,124
$ 1,579
$ 3,367
£ 1,263
£ 2,693

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at l’Olmo includes a talented local cook that shall prepare your evening meals. Breakfast is also included and prepared by the maid. Please note that food & wine are not included.

Weekly prices
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€ 2,941
€ 4,600
$ 3,169
$ 4,956
£ 2,535
£ 3,965

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable house with a beautiful garden, a private heated pool just minutes from the charming village of San Gemini. Satellite TV with DVD. Air-con. Wireless internet.

Weekly prices
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To
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€ 1,318
€ 2,190
$ 1,420
$ 2,360
£ 1,136
£ 1,888

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at Il Cerro includes a talented local cook that shall prepare your evening meals. Breakfast is also included prepared by the maid. Please note that Food & winne is not included.

Weekly prices
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To
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€ 2,793
€ 3,665
$ 3,010
$ 3,950
£ 2,408
£ 3,160

SLEEPING: 5 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable house with a beautiful garden, a private heated pool just minutes from the charming village of San Gemini. Satellite TV with DVD. Air-con. Wireless internet.

Weekly prices
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To
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€ 1,465
€ 2,523
$ 1,579
$ 2,719
£ 1,263
£ 2,175

SLEEPING: 5 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at Il Cerro includes a talented local cook that shall prepare your evening meals. Breakfast is also included prepared by the maid. Please note that Food & winne is not included.

Weekly prices
From
To
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€ 2,941
€ 3,999
$ 3,169
$ 4,309
£ 2,535
£ 3,447

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