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.

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Showing: 42 villas
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Showing: 42 villas

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 (and food) included in the price.

Weekly prices
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To
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€ 30,534
€ 30,534
$ 31,043
$ 31,043
£ 25,445
£ 25,445

SLEEPING: 22 - BEDROOMS: 11 - BATHROOMS: 12

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

This rental option for Podere Celli includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week, in addition to a hands-on cooking class before one of the dinners. The cost of food and drinks is not included.

Weekly prices
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€ 18,264
€ 27,194
$ 18,568
$ 27,647
£ 15,220
£ 22,662

SLEEPING: 26 - BEDROOMS: 13 - BATHROOMS: 14

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

Luxury fully air-con stone farmhouse in Chianti with a large private pool. Beautifully decorated bedrooms & luxury ensuite bathrooms. Professional kitchen & large dining loggia. Sauna [fees apply] & secure grounds.

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€ 14,074
€ 23,461
$ 14,309
$ 23,852
£ 11,728
£ 19,551

SLEEPING: 26 - BEDROOMS: 13 - BATHROOMS: 14

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

This rental option for Podere Celli includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week, in addition to a hands-on cooking class before one of the dinners. The cost of food and drinks is not included.

Weekly prices
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€ 20,272
€ 29,666
$ 20,610
$ 30,160
£ 16,893
£ 24,722

SLEEPING: 26 - BEDROOMS: 13 - BATHROOMS: 14

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

Plan an intimate wedding for up to 50 guests in a fully A/C luxury farmhouse. Tuscan interiors with ensuite bathrooms & well-equipped kitchen. Private travertine infinity pool, sauna, manicured gardens & stunning views.

Weekly prices
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€ 15,010
€ 24,395
$ 15,260
$ 24,801
£ 12,508
£ 20,329

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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€ 16,816
€ 22,209
$ 17,096
$ 22,580
£ 14,013
£ 18,508

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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€ 19,038
€ 25,382
$ 19,355
$ 25,805
£ 15,865
£ 21,152

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 8

  • 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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€ 12,121
€ 17,315
$ 12,323
$ 17,604
£ 10,101
£ 14,429

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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€ 17,315
€ 24,736
$ 17,604
$ 25,148
£ 14,429
£ 20,613

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • 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.

Weekly prices
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€ 14,740
€ 19,355
$ 14,985
$ 19,678
£ 12,283
£ 16,129

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 45 guests in the elegant & magnificent 16C Villa di Masseto. with a nearby country retreat ideal for your guests. Superb local concierge service.

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€ 21,374
€ 21,374
$ 21,730
$ 21,730
£ 17,812
£ 17,812

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.

Weekly prices
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€ 16,596
€ 22,122
$ 16,873
$ 22,491
£ 13,830
£ 18,435

New for 2025

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 11

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Exclusive fully-staffed sustainable villa. Luxury interiors with bespoke finishes. 17m heated infinity pool, in-villa spa with hammam sauna & turkish bath. All ensuite bathrooms. Panoramic views of Montagnola Senese Nature Reserve. Breakfast & 4 dinners included.

Weekly prices
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€ 16,671
€ 21,720
$ 16,949
$ 22,082
£ 13,893
£ 18,100
New villa, be the first to review

New for 2025

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 13

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Exclusive fully-staffed sustainable villa. Luxury interiors with bespoke finishes. 17m heated infinity pool, in-villa spa with hammam sauna & turkish bath. All ensuite bathrooms. Panoramic views of Montagnola Senese Nature Reserve. Breakfast & 4 dinners included.

Weekly prices
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€ 18,523
€ 24,133
$ 18,832
$ 24,536
£ 15,436
£ 20,111
New villa, be the first to review

New for 2025

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 8

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

Prestigious 16th-century Venetian villa near Vicenza with staff & cook. Elegant frescoed interiors, Italian gardens & private pool. Large A/C bedrooms, luxury kitchen & bathrooms. Breakfast service included in the price.

Weekly prices
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€ 22,901
€ 22,901
$ 23,282
$ 23,282
£ 19,084
£ 19,084
New villa, be the first to review

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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€ 10,647
€ 15,774
$ 10,824
$ 16,037
£ 8,872
£ 13,145

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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€ 16,004
€ 21,131
$ 16,270
$ 21,483
£ 13,336
£ 17,609

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.

Weekly prices
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€ 13,250
€ 19,544
$ 13,471
$ 19,869
£ 11,042
£ 16,286

New for 2025

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

Fully-staffed Medici fortress with 360-degree coastal views. Walk to bars, restaurants, beaches & beach clubs in Punta Ala. Grand interiors with A/C bedrooms. Breakfast & three dinners included.

Weekly prices
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€ 10,904
€ 18,791
$ 11,086
$ 19,104
£ 9,087
£ 15,659
New villa, be the first to review

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