Fully staffed and catered villas with chefs in Italy

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.

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Showing: 27 villas
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Showing: 27 villas

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

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

Large welcoming 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
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€ 2,813
€ 4,242
$ 3,814
$ 5,752
£ 2,705
£ 4,080

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 6

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

Large welcoming 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.

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€ 3,462
€ 5,221
$ 4,694
$ 7,079
£ 3,329
£ 5,021

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 9

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

Large welcoming 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.

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€ 4,328
€ 6,527
$ 5,868
$ 8,849
£ 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.   

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€ 6,535
€ 8,735
$ 8,860
$ 11,843
£ 6,284
£ 8,400

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

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

Historic 13th-century villa in Chianti with staff & cook, 30km from Florence. Classic Tuscan decor, terracotta floors and frescoed walls. A/C suites, modern en-suite bathrooms & fully-equipped kitchen. Private, gated pool on large, manicured garden. Breakfast service included in the rental price plus two dinners.

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€ 5,700
€ 8,500
$ 7,728
$ 11,524
£ 5,482
£ 8,174

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.

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€ 5,732
€ 8,451
$ 7,772
$ 11,458
£ 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. 

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€ 6,867
€ 9,587
$ 9,310
$ 12,998
£ 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.

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€ 3,928
€ 5,742
$ 5,326
$ 7,785
£ 3,778
£ 5,522

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
$ 6,266
$ 9,159
£ 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.

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€ 5,724
€ 7,858
$ 7,761
$ 10,654
£ 5,505
£ 7,557

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • 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.

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€ 1,889
€ 3,509
$ 2,561
$ 4,757
£ 1,817
£ 3,374

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.

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€ 2,362
€ 4,386
$ 3,202
$ 5,946
£ 2,271
£ 4,218

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.

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€ 997
€ 2,128
$ 1,352
$ 2,885
£ 959
£ 2,046

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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€ 2,113
€ 3,244
$ 2,865
$ 4,398
£ 2,032
£ 3,120

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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€ 1,109
€ 2,364
$ 1,503
$ 3,205
£ 1,066
£ 2,273

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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€ 2,225
€ 3,480
$ 3,016
$ 4,718
£ 2,140
£ 3,347

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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€ 997
€ 1,657
$ 1,352
$ 2,247
£ 959
£ 1,593

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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€ 2,113
€ 2,773
$ 2,865
$ 3,760
£ 2,032
£ 2,667

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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€ 1,109
€ 1,909
$ 1,503
$ 2,588
£ 1,066
£ 1,836

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
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€ 2,225
€ 3,025
$ 3,016
$ 4,102
£ 2,140
£ 2,909
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