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.

Condé Nast Traveller 2020 Award
Showing: 27 villas
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Showing: 27 villas

Sleeping: 12 - Bedrooms: 8 - Bathrooms: 7

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

Beautiful stone farmhouse on the edge of the Chianti near Florence. Large infinity edge pool & air con bedrooms. Large stylish outdoor seating area & stunning views. Rental option including a cook avail.

Weekly prices
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€ 4,610
€ 7,549
$ 6,250
$ 10,235
£ 4,433
£ 7,260

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

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

Beautiful stone farmhouse on the edge of the Chianti near Florence. Large infinity edge pool & air con bedrooms. Large stylish outdoor seating area & stunning views. Rental option including a cook avail.

Weekly prices
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€ 5,327
€ 8,623
$ 7,222
$ 11,691
£ 5,122
£ 8,293

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

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

This staffed rental option at Il Cortile includes a professional chef that shall prepare 6 fantastic evening meals and  breakfast. Please note that food and wine is not included and that cookings lessons can be arranged. 

Weekly prices
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€ 7,870
€ 11,659
$ 10,670
$ 15,808
£ 7,568
£ 11,212

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

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

This rental option new for 2019 at Il Cortile Pratolino includes traditional or vegetarian cooking lessons & food experiences, alongside the chef & staff who will prepare breakfast and evening meals included in the rental price.

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€ 11,829
€ 15,619
$ 16,038
$ 21,176
£ 11,376
£ 15,020

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 5

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

Large, elegant farmhouse & guest house with a private pool near Florence. Air-con bedrooms in main house. Modern bathrooms. lovely garden and spectacular views. Shaded terrace ideal for al fresco meals.

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€ 3,943
€ 6,421
$ 5,345
$ 8,706
£ 3,791
£ 6,175

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 7

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

Host and celebrate here your wedding just, 30 minutes from Florence. Extensive grounds ideal for hosting a wedding up to 200 guests. Church San Michele a Rupecanina within walking distance.

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€ 5,970
€ 10,391
$ 8,094
$ 14,089
£ 5,741
£ 9,993

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 7

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

This rental option includes fantastic local chefs who will prepare a pizza dinner upon arrival, breakfast for seven days and three dinners during the week. Cost of ingredients and drinks is not included. 

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€ 7,127
€ 11,328
$ 9,662
$ 15,358
£ 6,853
£ 10,894

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 8

  • Cook Included
  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Heated Pool

Staffed 16th century fully air-conditioned villa with a heated private pool set in the Chianti. Spacious bedrooms with en-suite bathrooms, Fantastic cook included preparing breakfast & 6 evening meals. Maid service.

Weekly prices
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€ 6,000
€ 10,800
$ 8,135
$ 14,643
£ 5,770
£ 10,386

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 8

  • Cook Included
  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Heated Pool

New rental option for 2020 which includes: chef services for breakfast & dinner, cooking classes, food & wine experiences. Elegant interiors with original terracotta & beamed ceilings. Internal lift, A/C in all rooms & large en-suite bathrooms. Private heated pool, hot tub, sauna & gym. On-site concierge. Sleeps up to 16.

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€ 9,617
€ 14,417
$ 13,039
$ 19,547
£ 9,249
£ 13,864

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

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

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
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€ 5,484
€ 8,599
$ 7,435
$ 11,659
£ 5,274
£ 8,270

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 4

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

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
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€ 5,773
€ 9,053
$ 7,827
$ 12,274
£ 5,552
£ 8,706

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 5

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

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
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€ 6,282
€ 9,851
$ 8,517
$ 13,356
£ 6,041
£ 9,473

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 5

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

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
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€ 6,791
€ 10,650
$ 9,208
$ 14,440
£ 6,531
£ 10,242

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 9

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

Luxury hilltop villa 18km from Orvieto with staff & cook. 25-acre park with formal gardens, fountain and private mosaic-paved pool. A/C in all rooms, modern en-suite bathrooms & professional kitchen. Antique painting collection, billiard table & internal lift. Breakfast service included in the rental price, plus two dinners. 

Weekly prices
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€ 7,250
€ 10,250
$ 9,830
$ 13,897
£ 6,972
£ 9,857

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

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

Luxury hill top farmhouse with large saltwater infinity pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook and cooking lessons available.

Weekly prices
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€ 4,500
€ 8,400
$ 6,101
$ 11,389
£ 4,328
£ 8,078

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

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

Luxury hill top farmhouse with large infinity-edge pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook & cooking lessons available.

Weekly prices
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€ 6,309
€ 10,208
$ 8,554
$ 13,840
£ 6,067
£ 9,817

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 9

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
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€ 4,315
€ 7,117
$ 5,850
$ 9,650
£ 4,150
£ 6,844

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 10

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
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€ 4,439
€ 7,396
$ 6,019
$ 10,027
£ 4,269
£ 7,112

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 11

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
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€ 4,722
€ 7,866
$ 6,403
$ 10,664
£ 4,541
£ 7,564

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 11

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

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

Weekly prices
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€ 6,927
€ 10,071
$ 9,392
$ 13,654
£ 6,662
£ 9,685

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 11

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

This rental option for Il Renaccio includes an everflowing supply of DOCG Vernaccia di San Gimignano red & white wine & the services of a professional chef for dinner 6 days a week. 

Weekly prices
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€ 8,438
€ 11,582
$ 11,440
$ 15,703
£ 8,114
£ 11,138

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Beautiful farmhouse with a Private pool set in vineyards just 3kms/2 miles from Siena. Professional kitchen, modern bathrooms. Hot tub. Walk to restaurants or get a bus into the center of Siena.

Weekly prices
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€ 2,434
€ 5,454
$ 3,300
$ 7,395
£ 2,341
£ 5,245

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, a welcome meal, a wine tasting experience in the estate’s wine cellars and evening meal, a cooking class with evening meal.

Weekly prices
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€ 4,376
€ 7,397
$ 5,933
$ 10,029
£ 4,209
£ 7,113

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Beautiful farmhouse with a Private pool set in vineyards just 3kms/2 miles from Siena. Professional kitchen, modern bathrooms. Hot tub. Walk to restaurants or get a bus into the center of Siena.

Weekly prices
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€ 3,149
€ 6,350
$ 4,269
$ 8,610
£ 3,028
£ 6,107

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, a welcome meal, a wine tasting experience in the estate’s wine cellars and evening meal, a cooking class with an evening meal.

Weekly prices
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€ 6,385
€ 9,588
$ 8,657
$ 12,999
£ 6,140
£ 9,220

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

This staffed rental option for Santa Dieci includes an everflowing supply of DOC Chianti red wine & the services of a professional chef for breakfast 6 days a week, dinner 3 days a week, a cooking class & wine tasting experience. 

Weekly prices
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€ 7,518
€ 10,721
$ 10,193
$ 14,535
£ 7,230
£ 10,310

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 6

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

Large stone farmhouse with staff and private heated pool, 15 mins from Siena. Fully air-conditioned and featuring beautiful gardens. Rental price includes daily breakfast service, one dinner and pizza lunch; excluding food and wine.

Weekly prices
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€ 6,272
€ 8,064
$ 8,504
$ 10,933
£ 6,032
£ 7,755

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 6

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

Large stone farmhouse with staff and private heated pool, 15 mins from Siena. Fully air-conditioned and featuring beautiful gardens. Rental price includes daily breakfast service, one dinner and pizza lunch; excluding food and wine.

Weekly prices
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To
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€ 7,280
€ 9,184
$ 9,870
$ 12,452
£ 7,001
£ 8,832

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • 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
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To
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€ 1,794
€ 3,511
$ 2,433
$ 4,760
£ 1,725
£ 3,376

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
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To
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€ 2,791
€ 5,461
$ 3,784
$ 7,404
£ 2,684
£ 5,252

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. Rental option with chef & all-inclusive wine available.

Weekly prices
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To
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€ 4,416
€ 7,318
$ 5,987
$ 9,922
£ 4,247
£ 7,038

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
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To
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€ 3,210
€ 6,293
$ 4,352
$ 8,532
£ 3,087
£ 6,051

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
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To
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€ 5,460
€ 8,864
$ 7,403
$ 12,018
£ 5,251
£ 8,525

Sleeping: 20 - Bedrooms: 9 - Bathrooms: 7

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

This staffed rental option for Santi Terzi includes an infinite supply of IGT Umbria white wine & the services of a professional chef for breakfast 6 days a week & dinner 4 days a week.

Weekly prices
From
To
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€ 7,585
€ 11,293
$ 10,284
$ 15,311
£ 7,294
£ 10,860
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