So many of our special places to stay have been around a long time — some for a very long time. A select few are heritage properties of significant historical importance. When you stay in these historic and heritage villas, you take your place in an authentic piece of Italian history. You will be joining an illustrious, centuries-old guest list.
Our exclusive collection of unique places to stay includes a grand Palladian villa with its own formal gardens; country homes built for wealthy princes during the 17th century; the main farmstead on the former Grand Duke of Tuscany’s estate; and even the rustic Umbrian home of a renowned Italian neoclassical sculptor. (Antonio Canova, who crafted a famous statue of George Washington for the state of North Carolina.)
And note, even when you are enjoying your slice of history, you will still find all the luxuries that make a stay memorable and comfortable. Every one of these estates and villas comes with its own private swimming pool. Most of our historic and heritage properties have air-conditioned bedrooms, so you get a good night’s sleep even in the height of summer. Many Tuscany Now & More villas have professional-standard kitchens, for those who want to indulge (or fire up) a passion for Italy’s renowned seasonal produce.
Our historic and heritage properties to rent sleep from 6 to 22 guests. At every one, you have free use of our travel concierge service. They can book you a table at the finest local restaurants or advise on local daytrips and tours, for those who want to investigate local history in even more depth. It’s all part of our award-winning service.
Best of all, this selection of historic and heritage properties in Italy is just one of many specially curated Tuscany Now & More collections. If you have a question about these properties, or any other villas in Italy, please get in touch.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 5
Design-led luxury villa near San Gimignano. 18m heated infinity pool, sauna & summer kitchen. Minimalist Wabi Sabi interiors in a converted medieval church. All ensuite bathrooms. Private hilltop position with 180° views
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
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
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: 6 - BEDROOMS: 3 - BATHROOMS: 3
Newly restored Renaissance-style villa with private pool & Italianate gardens 15km from Florence. Immaculate interiors with classic Tuscan decor & contemporary art collection. A/C in all rooms, ensuite bathrooms & modern kitchen. Large shaded loggia with outdoor living & dining areas.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6
Newly restored Renaissance-style villa with private pool & Italianate gardens 15km from Florence. Immaculate interiors with classic Tuscan decor & contemporary art collection. A/C in all rooms, ensuite bathrooms & modern kitchen. Large shaded loggia with outdoor living & dining areas.
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: 10 - BEDROOMS: 5 - BATHROOMS: 5
Contemporary luxury villa 5km from Castellina in Chianti. Chic interiors with authentic Tuscan charm. Heated gated pool & private tennis court set in lush olive groves. A/C bedrooms with all-ensuite bathrooms.
SLEEPING: 8 - BEDROOMS: 6 - BATHROOMS: 5
Elegant 17C country villa with a private pool near Venice. Air-con bedrooms, modern bathrooms. Stunning gardens with gated pool, small lake. Walk to bus stop for venice, shops, restaurants, tennis.
SLEEPING: 11 - BEDROOMS: 6 - BATHROOMS: 5
Elegant 17C country villa with a private pool near Venice. Air-con bedrooms, modern bathrooms. Stunning gardens with gated pool, small lake. Walk to bus stop for venice, shops, restaurants, tennis.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
Renaissance farmhouse in a lovely hilltop village, walking distance to amenities. Air-conditioned bedrooms with ensuite bathrooms. Garden with a private pool [heating available from 2026 for an extra fee] and pool house with summer kitchen. Shaded dining and lounging areas.
SLEEPING: 11 - BEDROOMS: 5 - BATHROOMS: 4
Renaissance farmhouse in a lovely hilltop village, walking distance to amenities. Air-conditioned bedrooms with ensuite bathrooms. Garden with a private pool [heating available from 2026 for an extra fee] and pool house with summer kitchen. Shaded dining and lounging areas.