Winter Villa Vacations

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.



Condé Nast Traveller 2023 Award
Showing: 19 villas
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Showing: 19 villas

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

  • Maid included
  • Fully air-conditioned villa
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Charming country stone farmhouse with a private pool enjoying beautiful views of the countryside near the pretty town of Montaione. Air-con. bedrooms, en-suite bathrooms & professional kitchen.
 

Weekly prices
From
To
-
€ 5,098
€ 6,991
$ 5,493
$ 7,533
£ 4,395
£ 6,027

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5

  • Maid included
  • Fully air-conditioned villa
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Charming country stone farmhouse with a private pool enjoying beautiful views of the countryside near the pretty town of Montaione. Air-con. bedrooms, en-suite bathrooms & professional kitchen.
 

Weekly prices
From
To
-
€ 7,282
€ 9,987
$ 7,847
$ 10,762
£ 6,278
£ 8,610

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5

  • Maid included
  • Fully air-conditioned villa
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

For an intimate wedding with up to 18 guests in a romantic & very private villa set at the heart of an 84-acre estate. Fully A/C interiors. Magical villa grounds with outdoor living areas & private pool. Breathtaking views of rolling Tuscan hills. Onsite concierge.   

Weekly prices
From
To
-
€ 8,810
€ 11,515
$ 9,494
$ 12,409
£ 7,595
£ 9,927

Special rates for May and June

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

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.

Weekly prices
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To
-
€ 3,535
€ 5,331
$ 3,809
$ 5,745
£ 3,047
£ 4,596

Special rates for May and June

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

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.

Weekly prices
From
To
-
€ 5,050
€ 7,616
$ 5,442
$ 8,207
£ 4,353
£ 6,565

Special rates for May and June

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

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.   

Weekly prices
From
To
-
€ 8,193
€ 10,950
$ 8,828
$ 11,800
£ 7,063
£ 9,440

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 6,145
€ 9,382
$ 6,621
$ 10,110
£ 5,297
£ 8,088

SLEEPING: 14 - BEDROOMS: 6 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 5,536
€ 8,413
$ 5,965
$ 9,066
£ 4,772
£ 7,253

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

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.

Weekly prices
From
To
-
€ 4,117
€ 7,141
$ 4,436
$ 7,695
£ 3,549
£ 6,156

SLEEPING: 11 - BEDROOMS: 5 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

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.

Weekly prices
From
To
-
€ 4,574
€ 7,934
$ 4,929
$ 8,550
£ 3,944
£ 6,840

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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. 

Weekly prices
From
To
-
€ 3,457
€ 5,237
$ 3,725
$ 5,644
£ 2,980
£ 4,515

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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. 

Weekly prices
From
To
-
€ 4,067
€ 6,161
$ 4,382
$ 6,639
£ 3,506
£ 5,311

Special rates for May and June

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 2,998
€ 4,916
$ 3,230
$ 5,298
£ 2,584
£ 4,238

Special rates for May and June

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 3,195
€ 5,114
$ 3,443
$ 5,510
£ 2,754
£ 4,408

Special rates for May and June

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 3,357
€ 5,563
$ 3,618
$ 5,995
£ 2,894
£ 4,796

Special rates for May and June

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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. 

Weekly prices
From
To
-
€ 3,555
€ 5,761
$ 3,831
$ 6,208
£ 3,065
£ 4,967

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 2,765
€ 4,623
$ 2,980
$ 4,982
£ 2,384
£ 3,985

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 3,073
€ 5,126
$ 3,311
$ 5,523
£ 2,649
£ 4,419

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 3

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

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.

Weekly prices
From
To
-
€ 3,443
€ 5,727
$ 3,710
$ 6,171
£ 2,968
£ 4,937

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 1

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Hot tub

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.

Weekly prices
From
To
-
€ 1,463
€ 3,876
$ 1,577
$ 4,176
£ 1,261
£ 3,341

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 1

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Hot tub

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.

Weekly prices
From
To
-
€ 1,829
€ 4,446
$ 1,971
$ 4,791
£ 1,577
£ 3,833

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