Discover the enchanting magic of winter in Italy with our meticulously selected collection of villas, thoughtfully curated for the holiday season and beyond. Immerse yourself in the timeless charm of Tuscany, Umbria and Veneto, all within the allure of our exclusive villa collection.
Our winter villas are more than mere accommodations; they are a gateway to an unforgettable winter experience. This includes indulgent features like private heated pools and hot tubs for you to relax in, in-villa chefs and dedicated staff to cater to your every need, grand fireplaces inviting you to cosy up beside them, and elegantly designed interiors that exude warmth and comfort.
From staffed grand estates nestled in the heart of the Tuscan countryside to intimate boltholes near culture capitals, our winter villas in Italy can accommodate groups from from 2 to 24 people. Whether you’re seeking a romantic winter escape in the picturesque landscapes of Florence, Siena or San Gimignano, planning a family gathering in a water sun destination, or searching for the perfect location for a winter wedding in Italy, our villas are designed to make your winter dreams come true.
Each villa in our collection is an exclusive gem, available only through TN&M. Among our treasures, you’ll find an imposing 18th-century villa nested near Montepulciano and a charming converted Tuscan chapel surrounded by ancient cypress trees.
What sets us apart is our dedication to ensuring that every villa we list offers an authentic and unforgettable Italian experience. Our small, passionate team personally visaits or stays in each Italian villa, gaining intimate knowledge of the area. With over 30 years of experience, we excel in matching every guest to the perfect villa.
We take pride in keeping our portfolio small and selective to maintain the highest quality. That’s why you won’t find these unique villas listed on any other website. Our guests have spoken through their verified reviews, attesting to the exclusive Tuscany Now & More experience. Discover what they have to say about their remarkable stays, and let their experiences guide you toward your own Italian adventure.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6
Fantastic hill top villa with stunning views, just 30 mins from Florence. Ample outside shaded living & dining space. Private heated swimming pool with large air-con bedrooms & modern bathrooms.
SLEEPING: 14 - BEDROOMS: 6 - BATHROOMS: 4
Luxury home on a large estate with a heated private pool near Sansepolcro. Beautiful views, fantastic kitchen, air conditioned bedrooms, sophisticated bathrooms, stylishly furnished. Professional cook available.
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 gated pool 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 gated pool and pool house with summer kitchen. Shaded dining and lounging 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: 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: 6 - BEDROOMS: 3 - BATHROOMS: 3
Modern stone farmhouse with private heated pool under 1km from Poggibonsi, between Florence & Siena. A/C bedrooms with en-suite bathrooms. Panoramic outdoor living space terraced into the hillside with additional summer kitchen & dining loggia.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
Modern stone farmhouse with private heated pool under 1km from Poggibonsi, between Florence & Siena. A/C bedrooms with en-suite bathrooms. Panoramic outdoor living space terraced into the hillside with additional summer kitchen & dining loggia.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
15th century villa, part of a small hamlet in the hills of Florence. Large courtyard with a dining & seating area with a small garden & private heated pool. Very comfortably furnished with two air con bedrooms.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2
15th century villa, part of a small hamlet in the hills of Florence. Large courtyard with a dining & seating area with a small garden & private heated pool. Very comfortably furnished with two air con bedrooms.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 3
15th century villa, part of a small hamlet in the hills of Florence. Large courtyard with a dining & seating area with a small garden & private heated pool. Very comfortably furnished with two air con bedrooms.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2
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.
SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 1
17th-century stone farmhouse with A/C in all rooms, 20km from Florence. Tuscan interiors with terracotta floors, beamed ceilings & exposed stone. Private pool & hot tub. Manicured garden with outdoor dining area, olive trees & pomegranate trees.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 1
17th-century stone farmhouse with A/C in all rooms, 20km from Florence. Tuscan interiors with terracotta floors, beamed ceilings & exposed stone. Private pool & hot tub. Manicured garden with outdoor dining area, olive trees & pomegranate trees.