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.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6
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, excluding food.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 6
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, excluding food.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
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.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
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.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6
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.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6
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.
SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7
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.
SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3
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.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
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.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, two dinners, a cooking class & a wine tasting in the estate’s wine cellars.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 4
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.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 4
This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, two dinners, a cooking class & a wine tasting in the estate’s wine cellars.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3
Beautifully set villa in the hills just over 20 minutes' drive from the sandy beaches north of Lucca, with air-conditioned bedrooms, well-kept garden with lawns and a private spring water swimming pool [heated from 2024 for an extra fee]. Powered by solar energy, charging stations for electric cars available at an extra fee. Read our clients fantastic comments.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
Beautifully set villa in the hills just over 20 minutes' drive from the sandy beaches north of Lucca, with air-conditioned bedrooms, well-kept garden with lawns and a private spring water swimming pool [heated from 2024 for an extra fee]. Powered by solar energy, charging stations for electric cars available at an extra fee. Read our clients fantastic comments.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
This rental option at Villa Denise includes a professional cook that will prepare breakfast 6 days a week and dinner 3 days a week. Note that ingredients & drinks are not included. Maid service is also included on Saturday + 3 times during the week. Powered by solar energy, charging stations for electric cars available at an extra fee.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 4
Beautifully set villa in the hills just over 20 minutes' drive from the sandy beaches north of Lucca, with air-conditioned bedrooms, well-kept garden with lawns and a private spring water swimming pool [heated from 2024 for an extra fee]. Powered by solar energy, charging stations for electric cars available at an extra fee. Read our clients fantastic comments.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 4
This rental option at Villa Denise includes a professional cook that will prepare breakfast 6 days a week and dinner 3 days a week. Note that ingredients & drinks are not included. Maid service is also included on Saturday + 3 times during the week. Powered by solar energy, charging stations for electric cars available at an extra fee. Read our clients fantastic comments.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
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.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7
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.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7
This rental option includes a professional cook and waiter that shall prepare wonderful evening meals for 3 nights and daily breakfast at villa Gugliaie.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9
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.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9
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.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
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.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
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.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5
Converted farmhouse on organic wine estate with staff & cook. Private panoramic pool & A/C bedrooms. Short walk to winery, cooking school, restaurants & medieval village. Breakfast service included plus one dinner & wine tasting. On-site experiences.