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: 14 - BEDROOMS: 7 - BATHROOMS: 9
Restored luxury stone farmhouse & guesthouse with private heated infinity pool in Siena outskirts. Interior has terracotta floors, beamed ceilings, A/C in all rooms & en-suite bathrooms. Plenty of panoramic outdoor living & dining areas. Private gym.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
Luxury villa with stunning views overlooking San Gimignano with an oversized private swimming pool and full size tennis court. Air conditioned bedrooms with en suite bathrooms.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
This rental option for Diaspero includes services of a professional chef for breakfast 6 days a week and dinner upon arrival. The cost of food is included, but drinks are not included. Additional meals can be arranged as an extra.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 5
Luxury hilltop villa 18km from Orvieto with staff & cook. A/C interiors, antique painting collection & internal lift. Modern en-suite bathrooms & professional kitchen. 25-acre park with formal gardens & private mosaic-paved pool. Breakfast & dinner service included in the price.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 9
Luxury hilltop villa 18km from Orvieto with staff & cook. A/C interiors, antique painting collection & internal lift. Modern en-suite bathrooms & professional kitchen. 25-acre park with formal gardens & private mosaic-paved pool. Breakfast & dinner service included in the price.
SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5
Fully air conditioned luxury villa on the edge of the Chianti with a large private heated pool, en suite bathrooms, professional kitchen, fantastic outside living & dining areas. Superbly managed.
SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7
Fully air conditioned luxury villa on the edge of the Chianti with a large private heated pool, en suite bathrooms, professional kitchen, fantastic outside living & dining areas. Superbly managed.
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
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
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: 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: 14 - BEDROOMS: 7 - BATHROOMS: 7
Fully-staffed Tuscan townhouse near Florence, in charming Mugello village. Short walk to shops, restaurants & hiking trails. Elegant interiors, all-ensuite bathrooms & private pool. Breakfast & dinner service included in the price.
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!