Villas with all-inclusive wine in Italy

When you stay in our villas with all-inclusive wine, vino flows like water. Red, white or rosé; your cellar is always stocked, so you can drink like a true Italian while enjoying the luxuries of your private home in Italy. As the only collection of properties in the world that include unlimited wine in the rental price, this is a wine-lovers dream come true.

There's a popular expression here in Italy, “non puoi avere la botte piena e la moglie ubriaca” (“you can’t have a full barrel and a drunk wife”), but at TN&M we believe that our guests should never have to compromise. When you stay in our villas with wine included, you really can have it all.

Among our portfolio of handpicked villas with unlimited wine are luxury properties in Tuscany and Umbria. Each villa listed below is exclusive to TN&M, including a medieval tower on an organic farm overlooking Siena and a 400-year old stone farmhouse in Castellina in Chianti.  You will not find these villas listed on any other website. 

At Montaspro, Santa Dieci and Il Renaccio, the wines included in the rental price, are from the very vineyards you see. Stay among the vines and drink wine grown directly at the end of your garden. Some of these villas have a chef, maid and other staff included in the rental price. Your in-villa chef and housekeeper take care of the small things so you can concentrate on visiting the best wineries in Italy and tasting the niche wines of Tuscany and Umbria.   

Every single villa in this special collection has a private swimming pool and air-conditioned bedrooms — some even have air-conditioning throughout the property, including in the communal spaces. Our all-inclusive wine villas sleep from 2 to 20 guests. 

Your wine cellar will be stocked before your arrival so you can enjoy your villa from the very moment you step through the door. You’ll never have to worry about shopping for wine as your villa manager will regularly make sure the wine stock is topped up. TN&M has partnered with local wineries and villa owners to thoughtfully select wines that best express and embrace the regional identity. No two villas are the same, with each supporting local 0 km (“kilometro zero”) wineries on their doorstep.  While some may stock rosé and white wines, others might fill their cellars solely with quality reds. Whether your choice of wine is a juicy, full-bodied Chianti or a chilled, crisp Vernaccia di San Gimignano, there will always be a perfect villa best suited to your palate. 

Vino aficionados staying in our villas with all-inclusive wine have free use of our luxury concierge service for pre-trip arrangements, as well as an emergency number available 24/7 while in-destination. Your experienced concierges will tailor a trip around you and your travel party. They can arrange maid services, a private chef or babysitting so you can sit back, relax and soak up the calming rhythms of the Mediterranean. Our concierges can organise private cookery classes and sommelier-led tastings at the villa, and book you a table in the finest local trattorias or wineries. 

To see what other travellers think of our service, and the experience of staying in a Tuscany Now & More luxury villa, read our verified reviews.

Condé Nast Traveller 2022 Award
Showing: 11 villas
Sort by:
Select your currency:
Showing: 11 villas

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
-
€ 4,874
€ 8,575
$ 6,264
$ 11,021
£ 4,731
£ 8,324

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
-
€ 6,116
€ 10,701
$ 7,860
$ 13,753
£ 5,937
£ 10,388

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

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.  

Weekly prices
From
To
-
€ 7,244
€ 10,476
$ 9,310
$ 13,465
£ 7,032
£ 10,170

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

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 and drinks is not included. Additional meals can be arranged as an extra.

Weekly prices
From
To
-
€ 9,376
€ 12,609
$ 12,051
$ 16,206
£ 9,102
£ 12,240

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6

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

Renovated period palazzo with private heated pool in the medieval hill-town of San Gemini. A/C bedrooms with views & outdoor dining loggia. Enchanting stroll along cobbled streets to shops & restaurants. Rental option with cook available.

Weekly prices
From
To
-
€ 3,377
€ 6,608
$ 4,341
$ 8,493
£ 3,278
£ 6,415

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 6

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

This rental option for Santi Terzi includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week. The cost of food & drinks is not included. Rental option with chef & all-inclusive wine available.

Weekly prices
From
To
-
€ 5,343
€ 8,855
$ 6,868
$ 11,382
£ 5,187
£ 8,596

SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7

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

Renovated period palazzo with private heated pool in the medieval hill-town of San Gemini. A/C bedrooms with views & outdoor dining loggia. Enchanting stroll along cobbled streets to shops & restaurants. Rental option with cook available.

Weekly prices
From
To
-
€ 3,884
€ 7,614
$ 4,992
$ 9,787
£ 3,771
£ 7,392

SLEEPING: 20 - BEDROOMS: 9 - BATHROOMS: 7

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

This rental option for Santi Terzi includes services of a professional chef for breakfast 6 days a week and dinner 4 days a week. The cost of food & drinks is not included. Rental option with chef & all-inclusive wine available.

Weekly prices
From
To
-
€ 6,607
€ 10,726
$ 8,491
$ 13,786
£ 6,413
£ 10,412

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Converted 15th-century farmhouse surrounded by vineyards 3km from Panzano in Chianti. Large, private fenced pool. Spacious Tuscan interiors & large A/C bedrooms. Lush, terraced garden has stone terraces with shaded outdoor seating & dining area.

Weekly prices
From
To
-
€ 3,653
€ 5,358
$ 4,695
$ 6,886
£ 3,546
£ 5,201

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Restored stone farmhouse with private heated pool, 15km from Lucca. Interior has terracotta floors, beamed ceilings & A/C in all rooms. Manicured garden with outdoor living & dining areas. Easy walk to village shops & restaurants. Rental option with all-inclusive wine available.

Weekly prices
From
To
-
€ 2,194
€ 3,407
$ 2,821
$ 4,379
£ 2,130
£ 3,308

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Restored stone farmhouse with private heated pool, 15km from Lucca. Interior has terracotta floors, beamed ceilings & A/C in all rooms. Manicured garden with outdoor living & dining areas. Easy walk to village shops & restaurants. Rental option with all-inclusive wine available.

Weekly prices
From
To
-
€ 2,508
€ 3,894
$ 3,223
$ 5,005
£ 2,435
£ 3,780

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. Rental option with all-inclusive wine available. 

Weekly prices
From
To
-
€ 1,340
€ 3,548
$ 1,722
$ 4,560
£ 1,300
£ 3,444

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. Rental option with all-inclusive wine available. 

Weekly prices
From
To
-
€ 1,674
€ 4,071
$ 2,152
$ 5,232
£ 1,625
£ 3,951

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 9

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
From
To
-
€ 4,505
€ 7,431
$ 5,790
$ 9,550
£ 4,373
£ 7,213

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 10

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
From
To
-
€ 4,635
€ 7,721
$ 5,957
$ 9,924
£ 4,499
£ 7,496

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 11

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

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

Weekly prices
From
To
-
€ 4,981
€ 8,296
$ 6,402
$ 10,663
£ 4,835
£ 8,053

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Stone farmhouse in the peaceful hills near Pisa & Lucca with private swimming pool. Classic Tuscan interiors with A/C bedrooms & en-suite bathrooms. Garden with olive grove & panoramic views. Short walk to village square with shops, bars & restaurants. Rental option with all-inclusive wine available.

Weekly prices
From
To
-
€ 1,473
€ 2,830
$ 1,894
$ 3,637
£ 1,430
£ 2,747

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Stone farmhouse in the peaceful hills near Pisa & Lucca with private swimming pool. Classic Tuscan interiors with A/C bedrooms & en-suite bathrooms. Garden with olive grove & panoramic views. Short walk to village square with shops, bars & restaurants. Rental option with all-inclusive wine available.

Weekly prices
From
To
-
€ 1,636
€ 3,147
$ 2,103
$ 4,044
£ 1,589
£ 3,055

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

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.

Weekly prices
From
To
-
€ 2,685
€ 6,015
$ 3,451
$ 7,732
£ 2,606
£ 5,839

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

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.

Weekly prices
From
To
-
€ 3,308
€ 6,671
$ 4,251
$ 8,574
£ 3,211
£ 6,476

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, a welcome meal, a wine tasting experience in the estate’s wine cellars and evening meal, a cooking class with an evening meal.

Weekly prices
From
To
-
€ 6,705
€ 10,068
$ 8,617
$ 12,940
£ 6,508
£ 9,773

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

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.

Weekly prices
From
To
-
€ 3,506
€ 7,071
$ 4,506
$ 9,088
£ 3,403
£ 6,864

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 4

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

This staffed rental option at Santa Dieci includes continental breakfast for 6 mornings, a welcome meal, a wine tasting experience in the estate’s wine cellars and evening meal, a cooking class with an evening meal.

Weekly prices
From
To
-
€ 7,107
€ 10,672
$ 9,134
$ 13,716
£ 6,899
£ 10,360

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

Charming country villa with private infinity pool & hot tub 18km from San Gimignano. A/C bedrooms & ensuite bathrooms. Wealth of alfresco living areas. On-site attentive staff can prepare meals & offer cooking lessons.

Weekly prices
From
To
-
€ 3,988
€ 8,343
$ 5,126
$ 10,723
£ 3,871
£ 8,099

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

A food lover’s paradise complete with chef services for breakfast & dinner, plus one cooking class. A/C bedrooms & ensuite bathrooms. Private infinity pool & hot tub. On-site attentive concierge. 18km from San Gimignano. 

Weekly prices
From
To
-
€ 7,385
€ 11,740
$ 9,492
$ 15,090
£ 7,169
£ 11,397

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

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

Charming country villa with private infinity pool & hot tub 18km from San Gimignano. A/C bedrooms & ensuite bathrooms. Wealth of alfresco living areas. On-site attentive staff can prepare meals & offer cooking lessons.

Weekly prices
From
To
-
€ 4,786
€ 10,012
$ 6,151
$ 12,868
£ 4,646
£ 9,719

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

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

A food lover’s paradise complete with chef services for breakfast & dinner, plus one cooking class. A/C bedrooms with two family suites, perfect for younger families. Private infinity pool & hot tub. On-site concierge. 18km from San Gimignano.

Weekly prices
From
To
-
€ 8,183
€ 13,409
$ 10,517
$ 17,234
£ 7,943
£ 13,017

When to visit Tuscany & Umbria

Spring is one of the best seasons to visit Tuscany and Umbria. Temperatures are pleasant with an average daytime high of 23℃ (73℉) and a low of 11℃ (51℉) overnight. Make use of longer days to explore the great outdoors — a light jacket will do — but make sure to bring your camera to capture valleys ablaze with wild poppies, violets and roses. 

Oenophiles will find May the perfect time to visit. During the last weekend of the month, wineries all across Italy open their doors to the public for one of Italy’s most important wine tourism events, Cantine Aperte. If you prefer to discover under-the-radar, local wines, Mostra del Chianti in Montespertoli honours the traditions, practices and culture of Chianti wine, while Only Wine Festival in Citta del Castello celebrates niche and small property winemakers in Umbria.

Summer is the hottest and busiest season to visit. Daytime temperatures rise to an average high of 30℃ (86℉), and a low of 17℃ (62℉) overnight. You may prefer to dedicate more time to relaxing by the pool or enjoying a private wine tasting at your villa. Cultural festivals happen outdoors all summer including Jazz and Wine Festival in Montalcino, Puccini Festival in Lucca, Umbria Jazz in Perugia and Trasimeno Blues on the shores of Lago Trasimeno. 

Sunshine and blue skies carry Tuscany and Umbria into autumn and winter, with an average daytime high of 13℃ (55℉) and 4℃ (39℉) overnight. Summer has come to an end which means you can experience authentic Italy at your own pace. September and October are peak production time: grapes and olives have been harvested; truffle season is around the corner. 

About Our Handpicked All-Inclusive Wine Villas 

Concierge service

Everyone renting an all-inclusive wine villa gets free use of our luxury concierge service. If you want shopping stocked in your fridge on arrival, a private chef to cook everyone dinner for a special occasion, or a private sommelier to lead you through a fun wine tasting, just ask. Making your holiday lettings extra-special is all part of our service. While you are in destination, our 24-hour on-the-ground team are also available by phone or WhatsApp.

Checking in & out

You should check-in at your all-inclusive wine villa rental between 4 pm and 7 pm. We can accommodate different arrival times — just communicate this in advance to our office staff.  Upon arrival, the villa owner or caretaker will inspect the property with you and demonstrate appliances, equipment, and utilities.

Check-out is 10 am on the last day of your holiday rental. The villa owner or caretaker will arrive at 9 am to settle outstanding payments, if you have any. If you want to depart earlier, please let us know in advance.    

Cleaning

Both the luxury villa and your private swimming pool will be cleaned prior to your arrival. Some holiday villas have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with the vacation rentals involves cleaning and tidying but does not cover making beds, kitchen cleaning, laundry or ironing. Extra services can be organised via our dedicated Travel Concierge team.     

Bed linen & towels

Our Tuscany and Umbria holiday rentals include bed linens, bathroom and swimming pool towels for all guests. They are provided weekly, but it is entirely up to you how often you feel these need to be cleaned or changed. You can tailor these extra services and changes via our concierge.

Subscribe to our newsletter

loading
Searching for your villa