Fully staffed and catered villas with chefs in Italy

PRESS PLAY TO WATCH THE TEASER

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 2022 Award
Showing: 30 villas
Sort by:
Select your currency:
Showing: 30 villas

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 centre of Siena.

Weekly prices
From
To
-
€ 2,685
€ 6,015
$ 3,451
$ 7,732
£ 2,606
£ 5,839

SLEEPING: 8 - BEDROOMS: 4 - 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 centre of Siena.

Weekly prices
From
To
-
€ 3,308
€ 6,671
$ 4,251
$ 8,574
£ 3,211
£ 6,476

SLEEPING: 8 - BEDROOMS: 4 - 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
From
To
-
€ 6,705
€ 10,068
$ 8,617
$ 12,940
£ 6,508
£ 9,773

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 centre of Siena.

Weekly prices
From
To
-
€ 3,506
€ 7,071
$ 4,506
$ 9,088
£ 3,403
£ 6,864

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
From
To
-
€ 7,107
€ 10,672
$ 9,134
$ 13,716
£ 6,899
£ 10,360

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
From
To
-
€ 4,333
€ 6,333
$ 5,569
$ 8,140
£ 4,206
£ 6,148

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
From
To
-
€ 5,098
€ 7,451
$ 6,552
$ 9,576
£ 4,948
£ 7,233

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 3 nights and daily breakfast at villa Gugliaie. Please note that food & wine is not included.

Weekly prices
From
To
-
€ 7,512
€ 10,312
$ 9,655
$ 13,253
£ 7,292
£ 10,010

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
-
€ 4,632
€ 6,986
$ 5,954
$ 8,980
£ 4,497
£ 6,782

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 three evening meals, to be enjoyed at the villa in one of the any dining areas available at the villa.   

Weekly prices
From
To
-
€ 7,516
€ 10,046
$ 9,660
$ 12,911
£ 7,296
£ 9,752

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
From
To
-
€ 6,270
€ 9,460
$ 8,059
$ 12,159
£ 6,087
£ 9,183

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
From
To
-
€ 6,308
€ 9,300
$ 8,108
$ 11,953
£ 6,123
£ 9,028

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
From
To
-
€ 4,505
€ 7,431
$ 5,790
$ 9,550
£ 4,373
£ 7,213

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
From
To
-
€ 4,635
€ 7,721
$ 5,957
$ 9,924
£ 4,499
£ 7,496

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
From
To
-
€ 4,981
€ 8,296
$ 6,402
$ 10,663
£ 4,835
£ 8,053

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • 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
From
To
-
€ 5,516
€ 7,814
$ 7,089
$ 10,043
£ 5,354
£ 7,585

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
From
To
-
€ 2,750
€ 4,510
$ 3,535
$ 5,797
£ 2,670
£ 4,378

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
From
To
-
€ 3,740
€ 5,500
$ 4,807
$ 7,069
£ 3,631
£ 5,339

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
From
To
-
€ 3,080
€ 5,104
$ 3,959
$ 6,560
£ 2,990
£ 4,954

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
From
To
-
€ 4,070
€ 6,094
$ 5,231
$ 7,833
£ 3,951
£ 5,916

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
From
To
-
€ 1,206
€ 2,574
$ 1,551
$ 3,309
£ 1,171
£ 2,499

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
From
To
-
€ 2,557
€ 3,925
$ 3,286
$ 5,045
£ 2,482
£ 3,810

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
From
To
-
€ 1,341
€ 2,860
$ 1,724
$ 3,676
£ 1,302
£ 2,776

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
From
To
-
€ 2,692
€ 4,211
$ 3,460
$ 5,412
£ 2,613
£ 4,088

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
-
€ 1,206
€ 2,005
$ 1,550
$ 2,577
£ 1,171
£ 1,946

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
-
€ 2,557
€ 3,356
$ 3,286
$ 4,313
£ 2,482
£ 3,258

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
From
To
-
€ 1,341
€ 2,310
$ 1,724
$ 2,969
£ 1,302
£ 2,242

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
-
€ 2,692
€ 3,661
$ 3,460
$ 4,705
£ 2,613
£ 3,554

Subscribe to our newsletter

loading
Searching for your villa