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: 39 villas
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Showing: 39 villas

SLEEPING: 22 - BEDROOMS: 11 - BATHROOMS: 11

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

Hold a fairytale wedding with up to 60 special guests at Torre Palazzone, an enchanting medieval castle just 15km from Siena. Say ‘I do’ surrounded by the estate’s romantic olive groves, sit down to a wedding feast in the beautiful rustic barn then dance the night away in the magical villa courtyard.

Weekly prices
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€ 22,004
€ 25,114
$ 23,711
$ 27,063
£ 18,969
£ 21,650

SLEEPING: 22 - BEDROOMS: 11 - BATHROOMS: 11

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

Magnificent medieval castle near Siena with daily continental breakfast service & chef services for dinner. A/C bedrooms & ensuite bathrooms. Private heated pool with outdoor living & dining areas. Short walk to village & winery. 

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€ 19,742
€ 22,965
$ 21,273
$ 24,747
£ 17,019
£ 19,798

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

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

One of our most exclusive villas with staff & cook 3km from Montepulciano. Design-led interiors, spacious A/C bedrooms & luxury en-suite bathrooms. Private infinity pool, large garden with unforgettable views of Pienza. Breakfast & dinner service included in the price.

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€ 24,046
€ 24,046
$ 26,101
$ 26,101
£ 20,552
£ 20,552

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

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

One of our most exclusive villas with staff & cook 3km from Montepulciano. Design-led interiors, spacious A/C bedrooms & luxury en-suite bathrooms. Private infinity pool, large garden with unforgettable views of Pienza. Breakfast & dinner service included in the price.

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€ 26,718
€ 26,718
$ 28,790
$ 28,790
£ 23,032
£ 23,032

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7

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

Magnificent villa with a private pool near Fiesole within easy reach of Florence. Air-conditioned luxury bedrooms & en suite bathrooms. Beautiful interiors and Glorious gardens. Fantastic local concierge. Breakfast dinner service included in the price.

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€ 14,038
€ 18,434
$ 15,238
$ 20,009
£ 11,998
£ 15,755

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 9

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

Magnificent villa with a private pool near Fiesole within easy reach of Florence. Air-conditioned luxury bedrooms & en suite bathrooms. Beautiful interiors and Glorious gardens. Fantastic local concierge. Breakfast dinner service included in the price.

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€ 15,806
€ 21,069
$ 17,157
$ 22,870
£ 13,510
£ 18,008

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 9

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

Host an Intimate wedding ceremony for up to 60 guests in the elegant & magnificent 16C Villa di Masseto. with a nearby country retreat ideal for your guests. Superb local concierge service. Breakfast & dinner service included in the price.

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€ 19,012
€ 24,275
$ 20,637
$ 26,350
£ 16,250
£ 20,748

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 11

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

18th-century villa with staff & cook 9km from Montepulciano. Restored period interiors, frescoed ceilings & lift. Private pool, A/C in all rooms & bedrooms with en-suite bathrooms. Easy stroll to shops & restaurants. Breakfast & dinner service included in the price.

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€ 16,015
€ 21,152
$ 17,384
$ 22,960
£ 13,688
£ 18,078

SLEEPING: 24 - BEDROOMS: 12 - BATHROOMS: 14

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

18th-century villa with staff & cook 9km from Montepulciano. Restored period interiors, frescoed ceilings & lift. Private pool, A/C in all rooms & bedrooms with en-suite bathrooms. Easy stroll to shops & restaurants. Breakfast & dinner service included in the price.

Weekly prices
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€ 18,130
€ 24,174
$ 19,679
$ 26,240
£ 15,496
£ 20,661

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

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

Luxurious hilltop farmhouse south of Siena with staff & cook. Large A/C bedrooms & modern en-suite bathrooms. Private pool, tennis court, football pitch, gym & sauna. Breakfast & dinner service included in the price.

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€ 9,894
€ 14,135
$ 10,740
$ 15,343
£ 8,457
£ 12,081

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 10

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

Luxurious hilltop farmhouse south of Siena with staff & cook. Large A/C bedrooms & modern en-suite bathrooms. Private pool, tennis court, football pitch, gym & sauna. Breakfast & dinner service included in the price.

Weekly prices
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€ 16,491
€ 23,558
$ 17,900
$ 25,572
£ 14,095
£ 20,135

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Luxury 12th Century Villa with beautiful views near Florence amid vineyards and olive groves. Immaculately maintained with gorgeous gardens. Air-con bedrooms. Private fenced pool [heated from 2024]. Estate T. Court.

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€ 17,556
€ 22,352
$ 19,057
$ 24,262
£ 15,005
£ 19,104

SLEEPING: 15 - BEDROOMS: 8 - BATHROOMS: 7

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

Luxury stone farmhouse in Chianti with staff & cook. Private infinity pool, multiple alfresco living spaces & large A/C bedrooms with luxurious ensuite bathrooms. On-site concierge. Breakfast & dinner service included. 

Weekly prices
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€ 10,140
€ 15,023
$ 11,007
$ 16,307
£ 8,667
£ 12,840

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.

Weekly prices
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€ 15,241
€ 20,124
$ 16,544
$ 21,844
£ 13,027
£ 17,200

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 6

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

A 16th-century architectural jewel of Veneto with staff & cook. Starred in "The Merchant of Venice" with Al Pacino. Frescoed interiors, Italian gardens & private heated pool. Large A/C bedrooms & modern kitchen. Breakfast & dinner service included in the price.

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€ 12,619
€ 18,613
$ 13,698
$ 20,204
£ 10,785
£ 15,909

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Elegant 17th-century villa with a private pool surrounded by a stunning park which includes an amphitheatre. Air-conditioned bedrooms with en suite bathrooms. Breakfast service [ingredients excluded] and maid service included.

Weekly prices
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€ 8,829
€ 13,856
$ 9,584
$ 15,041
£ 7,546
£ 11,843

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

For an Umbrian wedding with up to 50 guests (up to 90 with an extra fee) in a 17th-century villa with private pool, surrounded by 10-acre park with formal gardens, fountains & amphitheatre. A/C bedrooms with ensuite bathrooms. Breakfast service [ingredients excluded] and maid service included.

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€ 11,036
€ 17,321
$ 11,979
$ 18,801
£ 9,433
£ 14,804

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Stylish 16th-century luxury villa in Chianti with staff & cook. Terraced garden with outdoor living & dining areas. Private heated pool, gym & wellness area with treatment room and sauna [wellness area services available to those purchasing treatments]. Elegant interiors, internal lift & A/C in all rooms. On-site concierge. Breakfast & dinner included in the rental price.

Weekly prices
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€ 11,446
€ 17,223
$ 12,424
$ 18,695
£ 9,783
£ 14,721

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