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 2021 Award
Showing: 30 villas
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Showing: 30 villas

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Multi-generational family farmhouse with air-conditioned bedrooms, lots of en suite bathrooms and a private swimming pool with plenty of shaded outdoor living areas near the beautiful town of Massa Martana.

Weekly prices
From
To
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€ 4,328
€ 6,527
$ 6,099
$ 9,199
£ 4,162
£ 6,277

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

This rental option at Solomonio includes a breakfast buffet and a chef that shall prepare four evening meals, to be enjoyed at the villa in one of the any dining areas available at the villa.   

Weekly prices
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€ 6,535
€ 8,735
$ 9,210
$ 12,310
£ 6,284
£ 8,400

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook Included
  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Historic Chianti villa with staff & cook 30km from Florence. Tuscan decor, terracotta floors and frescoed walls. A/C suites, en-suite bathrooms & fully-equipped kitchen. Private, gated pool on large, manicured garden. Breakfast & dinner service included in the price.

Weekly prices
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€ 5,700
€ 8,600
$ 8,033
$ 12,120
£ 5,482
£ 8,270

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Cook Included
  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Converted 400-year-old farmhouse with staff & cook. Beamed ceilings, terracotta floors, A/C bedrooms & en-suite bathrooms. Fenced grounds with private pool & shaded outdoor dining. Breakfast & dinner service included in the price.

Weekly prices
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To
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€ 5,600
€ 8,500
$ 7,892
$ 11,979
£ 5,385
£ 8,174
No reviews for this villa

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. Rental option with all-inclusive wine available.

Weekly prices
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€ 5,732
€ 8,451
$ 8,079
$ 11,911
£ 5,513
£ 8,127

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook Included
  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

This rental option for Montesassi includes an unlimited supply of IGT Chianti white & rosé wine & the services of a professional chef for breakfast 6 days a week & dinner 4 days a week. 

Weekly prices
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€ 6,867
€ 9,587
$ 9,678
$ 13,511
£ 6,604
£ 9,220

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool

Fantastically located on the famous “Corsini” Chianti  wine estate 15 mins from Florence. Private pool  A/C bedrooms, en-suite bathrooms. 5 min walk to shops & restaurants.  Option including a cook avail.

Weekly prices
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€ 4,127
€ 6,032
$ 5,816
$ 8,501
£ 3,968
£ 5,800

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool

Fantastically located on the famous “Corsini” Chianti  wine estate 15 mins from Florence. Private pool  A/C bedrooms, en-suite bathrooms. 5 min walk to shops & restaurants.  Option including a cook avail.

Weekly prices
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€ 4,622
€ 6,755
$ 6,514
$ 9,521
£ 4,445
£ 6,497

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool

This rental option includes a professional cook and waiter that shall prepare wonderful evening meals for 6 nights at villa Gugliaie. Please note that food & wine is not included. Breakfast can also be arranged as an extra.

Weekly prices
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€ 5,724
€ 7,858
$ 8,067
$ 11,074
£ 5,505
£ 7,557

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook Included
  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Medieval staffed villa on hilltop 12km from Orvieto with private cook. A/C bedrooms & modern en-suite bathrooms. Lush, planted garden with private pool & outdoor living areas. Easy walk to village shops & restaurants. Breakfast & dinner service included in the price.

Weekly prices
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€ 5,060
€ 7,169
$ 7,132
$ 10,104
£ 4,867
£ 6,894
No reviews for this villa

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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€ 2,500
€ 4,100
$ 3,523
$ 5,778
£ 2,404
£ 3,943
No reviews for this villa

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. Breakfast included in the price. 

Weekly prices
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To
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€ 3,400
€ 5,000
$ 4,792
$ 7,047
£ 3,270
£ 4,808
No reviews for this villa

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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€ 2,800
€ 4,640
$ 3,946
$ 6,539
£ 2,693
£ 4,462
No reviews for this villa

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. Breakfast included in the price. 

Weekly prices
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To
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€ 3,700
€ 5,540
$ 5,215
$ 7,808
£ 3,558
£ 5,328
No reviews for this villa

SLEEPING: 9 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Food Included
  • Internet Connection
  • Private Pool

Hilltop Tuscan farmhouse with staff & cook, 15km from Florence. Classic Tuscan decor, en-suite bathrooms & fully-equipped country kitchen. Gated garden has private pool & outdoor dining loggia with sweeping views of Florence. Breakfast service included in the rental price plus three dinners (ingredients excluded) including on Saturday on arrival, once during the week and on Friday.

Weekly prices
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€ 2,952
€ 5,482
$ 4,160
$ 7,726
£ 2,839
£ 5,272

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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€ 1,097
€ 2,340
$ 1,546
$ 3,298
£ 1,055
£ 2,251

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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To
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€ 2,324
€ 3,568
$ 3,276
$ 5,029
£ 2,235
£ 3,432

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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To
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€ 1,220
€ 2,600
$ 1,719
$ 3,664
£ 1,173
£ 2,500

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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To
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€ 2,447
€ 3,828
$ 3,449
$ 5,395
£ 2,354
£ 3,681

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
From
To
-
€ 1,097
€ 1,823
$ 1,545
$ 2,569
£ 1,055
£ 1,753

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
From
To
-
€ 2,324
€ 3,051
$ 3,276
$ 4,299
£ 2,235
£ 2,934

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
-
€ 1,219
€ 2,100
$ 1,719
$ 2,960
£ 1,173
£ 2,019

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
-
€ 2,447
€ 3,328
$ 3,449
$ 4,690
£ 2,354
£ 3,200

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