Our handpicked Autumn villas are perfect for making the most of Italy during the shoulder season. Choose from our exclusive portfolio of luxury villa rentals in Tuscany, Umbria and Veneto, which bring some of Italy’s most popular destinations straight to your doorstep. With private heated pools, stunning views and plenty of peace and privacy, experience an Italy that is personal and slower paced.
Autumn is the perfect season in Italy for travellers wishing to experience Italy at its peaceful best, with fewer crowds and more meaningful local encounters. From September onwards the wine and olive harvest are in full swing and many wineries open their doors to guests wanting to help handpick the grapes.
The milder weather is ideal for exploring the country’s many UNESCO World Heritage Sites, like the Val d’Orcia and rolling hills of Prosecco country. Enjoy coastal hikes and white sandy beaches all to yourself, as well as horseback riding through the stunning Chianti region. Autumn is the season for white truffles, best enjoyed with visits to low-key truffle festivals and truffle hunting excursions.
Whether your idea of a perfect Italian vacation means enjoying iconic hilltowns like San Gimignano without the crowds, or savouring seasonal local dishes like Ribollita and Peposo, there are countless reasons to visit Italy in the Autumn.
Our luxury villas in Italy promise total privacy, while also being within easy reach of landmark destinations like Florence, Siena and Orvieto. Our fully-staffed villas offer the same amenities as a luxury hotel on a purely exclusive level. Our villas with heated pools are always warm enough to jump right in, while some villas even offer spa facilities for the ultimate bespoke luxury spa retreat in Tuscany. And, with the bonus of more space, comfort and privacy, villas are a haven for children and beloved pets.
SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7
Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and Chef service for 6 breakfast is also included in the price.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 8
Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and chef service for 6 breakfast included in the price.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6
Fully-staffed 19th-century heritage villa near Lake Maggiore. Located in an idyllic Piedmont village within walking distance of bars, restaurants & shops. Luxury renovated interiors, private heated pool, A/C bedrooms.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 9
Fully-staffed Positano villa. Walk to beaches, restaurants & shops. Bright open-plan interiors, expansive terrace with jaw dropping coastal views, two hot tubs, private heated pool & spa facilities. Breakfast service included in the price.
SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8
Grand villa just 3km from historic Lucca. Contemporary interiors & ensuite bathrooms. Idyllic gardens, hot tub & infinity pool set in 6-acres of private parkland. Walk to the local bakery and cycle into Lucca. Dedicated house manager.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9
Grand villa just 3km from historic Lucca. Contemporary interiors & ensuite bathrooms. Idyllic gardens, hot tub & infinity pool set in 6-acres of private parkland. Walk to the local bakery and cycle into Lucca. Dedicated house manager.
SLEEPING: 24 - BEDROOMS: 12 - BATHROOMS: 12
Grand villa just 3km from historic Lucca. Contemporary interiors & ensuite bathrooms. Idyllic gardens, hot tub & infinity pool set in 6-acres of private parkland. Walk to the local bakery and cycle into Lucca. Dedicated house manager.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 8
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.
SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 10
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.
SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 11
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.
SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 13
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.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 8
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.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 6
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.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 7
Fully-staffed family villa within hamlet 12km from Siena. Modern A/C bedrooms & ensuite bathrooms. Historic, peaceful setting with private, gated pool & manicured gardens with olive groves. Breakfast & dinner service included in the price.
SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7
Fully-staffed family villa within hamlet 12km from Siena. Modern A/C bedrooms & ensuite bathrooms. Historic, peaceful setting with private, gated pool & manicured gardens with olive groves. Breakfast & dinner service included in the price.
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
From fully-staffed Chianti farmhouses and historic villas on wine estates to a contemporary eco-villa on the Grosseto coast, our Autumn vacation rentals in Italy sleep from 6 to 18 people. So whether you are planning a family escape for October Half Term or a getaway with friends without the summer heat or crowds, we can accommodate all your needs and interests.
This special collection of luxury villas in Tuscany, Umbria and Veneto offer private heated swimming pools, hot tubs and exclusive access to local wine estates. Make the most of hearty autumn cuisine at our fully-staffed villas with chef and maid services included in the rental price. Your in-villa chef and housekeeper will keep you well-fed and feeling at home, so you can concentrate on enjoying the delights of Italy in the Fall.
When you book your villa with Tuscany Now & More you gain access to our Complimentary Concierge Service, who will help add those special personal touches to your autumn vacation. From pre-trip arrangements and additional services, like shopping delivered to your villa, our award-winning team can make it happen. Make the most of Italy in Autumn with local experiences, like Truffle hunting, winery tours, and sommelier-led wine tastings at your villa. You’ll also be given an emergency number available 24/7 for anything you may need while you are in destination.
Each villa in this collection is exclusive to Tuscany Now & More. Someone from our small team visits or stays in every Italian villa we list and knows the area. In fact, we have more than 30 years experience matching every guest to the right villa. This is why we keep our portfolio small and why you will not find this selection of villas listed on any other website. Just read our verified reviews to see what our guests think of the exclusive Tuscany Now & More experience!