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: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Cook included
  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Large stone farmhouse with staff and private heated pool, 15 mins from Siena. Fully air-conditioned and featuring beautiful gardens. Rental price includes daily breakfast service, excluding food.

Weekly prices
From
To
-
€ 9,577
€ 12,313
$ 10,632
$ 13,669
£ 8,116
£ 10,435

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 6

  • Cook included
  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Large stone farmhouse with staff and private heated pool, 15 mins from Siena. Fully air-conditioned and featuring beautiful gardens. Rental price includes daily breakfast service, excluding food.

Weekly prices
From
To
-
€ 11,116
€ 14,023
$ 12,340
$ 15,568
£ 9,420
£ 11,884

Special rates for October 

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
-
€ 3,712
€ 5,598
$ 4,120
$ 6,214
£ 3,145
£ 4,744

Special rates for October 

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
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To
-
€ 5,302
€ 7,997
$ 5,886
$ 8,878
£ 4,493
£ 6,777

Special rates for October 

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
-
€ 8,602
€ 11,498
$ 9,550
$ 12,765
£ 7,290
£ 9,744

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 11

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

18th-century villa with staff & cook 9km from Montepulciano. Restored period interiors, frescoed ceilings & lift. Private pool, A/C in all rooms & bedrooms with en-suite bathrooms. Easy stroll to shops & restaurants. Breakfast & dinner service included in the price.

Weekly prices
From
To
-
€ 16,816
€ 22,209
$ 18,668
$ 24,656
£ 14,251
£ 18,822

SLEEPING: 24 - BEDROOMS: 12 - BATHROOMS: 14

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

18th-century villa with staff & cook 9km from Montepulciano. Restored period interiors, frescoed ceilings & lift. Private pool, A/C in all rooms & bedrooms with en-suite bathrooms. Easy stroll to shops & restaurants. Breakfast & dinner service included in the price.

Weekly prices
From
To
-
€ 19,038
€ 25,382
$ 21,135
$ 28,179
£ 16,134
£ 21,510

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Heated pool
  • Tennis court

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.

Weekly prices
From
To
-
€ 10,389
€ 14,842
$ 11,534
$ 16,477
£ 8,804
£ 12,578

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 10

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Heated pool
  • Tennis court

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.

Weekly prices
From
To
-
€ 17,315
€ 24,736
$ 19,223
$ 27,461
£ 14,674
£ 20,963

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Elegant hilltop 17th-century villa in the Chianti, near Greve and Florence. Beautiful views with a private infinity-edge heated pool. Fully air-conditioned with luxury bathrooms & a large well-equipped kitchen.

Weekly prices
From
To
-
€ 8,708
€ 16,328
$ 9,667
$ 18,127
£ 7,380
£ 13,837

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 10

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

Elegant hilltop 17th-century villa in the Chianti, near Greve and Florence. Beautiful views with a private infinity-edge heated pool. Fully air-conditioned with luxury bathrooms & a large well-equipped kitchen.

Weekly prices
From
To
-
€ 9,580
€ 17,961
$ 10,635
$ 19,940
£ 8,118
£ 15,221

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Luxury home, fully air-conditioned with beautiful views part of a small hamlet within walking distance to the centre of Florence. Private heated infinity pool and en suite bathrooms.

Weekly prices
From
To
-
€ 7,776
€ 11,870
$ 8,633
$ 13,178
£ 6,590
£ 10,059

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Luxury home, fully air-conditioned with beautiful views part of a small hamlet within walking distance to the centre of Florence. Private heated infinity pool and en suite bathrooms.

Weekly prices
From
To
-
€ 8,190
€ 13,007
$ 9,092
$ 14,440
£ 6,941
£ 11,023

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool

Luxury home, fully air-conditioned with beautiful views part of a small hamlet within walking distance to the centre of Florence. Private heated infinity pool and en suite bathrooms.

Weekly prices
From
To
-
€ 10,238
€ 16,258
$ 11,365
$ 18,050
£ 8,676
£ 13,778

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
From
To
-
€ 7,474
€ 11,721
$ 8,297
$ 13,012
£ 6,334
£ 9,933

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 4

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
From
To
-
€ 7,867
€ 12,337
$ 8,734
$ 13,697
£ 6,667
£ 10,455

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
From
To
-
€ 8,562
€ 13,426
$ 9,505
$ 14,905
£ 7,256
£ 11,378

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Beautiful home with private pool & tennis court including a private cook for breakfast & evening meals on the famous Camugliano Estate. A/C bedrooms, sofisticated outdoor dining & living areas.

Weekly prices
From
To
-
€ 9,256
€ 14,515
$ 10,275
$ 16,114
£ 7,844
£ 12,300

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

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

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

Weekly prices
From
To
-
€ 6,733
€ 10,389
$ 7,475
$ 11,533
£ 5,706
£ 8,804

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

Weekly prices
From
To
-
€ 8,763
€ 13,522
$ 9,729
$ 15,011
£ 7,426
£ 11,459

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 8

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

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

Weekly prices
From
To
-
€ 8,416
€ 12,986
$ 9,344
$ 14,417
£ 7,132
£ 11,005

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

Luxury hill top farmhouse with large saltwater infinity pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook and cooking lessons available.

Weekly prices
From
To
-
€ 5,563
€ 10,384
$ 6,176
$ 11,528
£ 4,714
£ 8,800

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

Luxury hill top farmhouse with large infinity-edge pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook & cooking lessons available.

Weekly prices
From
To
-
€ 7,799
€ 12,617
$ 8,658
$ 14,008
£ 6,609
£ 10,693

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

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.

Weekly prices
From
To
-
€ 5,578
€ 10,731
$ 6,193
$ 11,913
£ 4,727
£ 9,094

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

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

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.

Weekly prices
From
To
-
€ 7,000
€ 13,164
$ 7,771
$ 14,614
£ 5,932
£ 11,156

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