Villas in Italy

Italy, of course, is the country of romance, iconic wine and even more iconic food, it is picture-postcard landscapes of rolling vineyards, cypress trees and passionate sunsets. It is the same country that has brought us Gelato and Leonardo da Vinci. From soil rich with ancient history and noble grapes to awe-inspiring masterpieces of art and architecture, there is much to adore about Italy and we are here to help you curate your unique relationship with the country.

Whether you are captivated by the romance of Venice and Verona, the dramatic coastline of Portofino and the Italian Riviera, the timeless landscapes of Tuscany and Umbria with sprawling vineyards, cypress groves and Renaissance masterpieces, or the capital of la dolce vita itself, Rome, the ‘Eternal City’, we’re here to help you find your dream holiday destination. 

From lovingly restored, rustic farmhouses, sleek, modern and solar-powered villas to noble, historic estates, our luxury holiday rentals in Italy sleep from 2 to 46 people. So, whether you are planning a romantic retreat, a grand family reunion or even a destination wedding, we can accommodate all your needs and interests; just see our tailored villa collections. Almost all of our luxury villas have air-conditioned bedrooms as well and many others have air-conditioning throughout the communal spaces, which is a welcome relief during the hot Italian summer. 

At Tuscany Now & More we take pride in our service. We have 30 years of experience, matching every guest to the right villa. Someone from our small team visits or stays in every Italian villa we list and knows the area. This is why we keep our portfolio small — and probably why the world’s leading luxury travel magazine says we’re one of Italy’s top five villa rental companies. 

Every Tuscany Now & More villa has a private swimming pool, free use of our concierge service, for pre-trip arrangements and an emergency number available 24/7 while you are in destination. Your concierge can arrange a private chef, daily maid service, or shopping delivered to your villa, and memorable experiences like Italian cookery classes in your holiday rental’s kitchen. 

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

About Italy

It may seem hard to believe that Italy has only existed as a unified country for around 150 years 一 yes, Italy, the iconic boot-shaped peninsula that has seen ancient empires rise and fall… first the Etruscans, then the Romans. Until the mid-to-late 19th century Italy was made up of multiple independent city-states or republics 一 think of the far-flung Venetian Empire, Renaissance powerhouses like Florence, Siena, Pisa and Mantua, the Duchy of Milan 一 each with their remarkable histories and traditions, unique cuisine and dialect. This may partly explain why regional identities are so passionately upheld throughout Italy and why your experience of Tuscany won’t be the same as that of LazioVeneto or even neighbouring Umbria

What to do in Italy

Where do we even begin in a country that does have it all? 

From the iconic domes of the Basilica di San Marco in Venice to those of Saint Peter’s in Rome with Florence’s Duomo somewhere in between, our luxury villas across Italy are ideally situated for exploring the abundance of art and historical landmarks the country has to offer. 

Visit Palladian villas in Veneto and Medici villas in Tuscany, enjoy coastal walks in Portofino and beach days near Pisa. From outdoor arias at the Verona Arena to saxophone solos at Umbria Jazz Festival; each region in Italy has an endless itinerary of cultural experiences for you to discover. We can even arrange personalised experiences like truffle hunting in the Tuscan hills, private gondola rides along the river Arno, walking tours in Venice or Siena. 

Tuscany and northern Lazio are great bases for those who love ancient history, both areas are rich with Etruscan and Roman ruins. Umbria, Italy’s ‘Green Heart’ is ideal for outdoor lovers with an outstanding rural landscape to rival that of Tuscany. Head to Portofino, Italy’s answer to the Cote d'Azur, for dramatic sea views, superyachts and quaint Romanesque churches. As a rule, if art is what you are after, Florence is always a good idea. 

For more ideas on what to do in Italy and where to stay, read our historic city guides and discover our favourite towns and villages

Food & Drink in Italy 

Italy has such a unique love language with food, much of the country’s culture and way of life is rooted in the culinary arts. On a national level, Italy is the birthplace of classic dishes like Carbonara, Bistecca alla Fiorentina and Tiramisu, but many traditional recipes are also a source of immense regional pride. In Northern Italian cities like Venice and Verona, staples like risotto and polenta outshine the kinds of hearty hand-made pasta dishes that are abundant in central Italy. Where you’ll happily enjoy rich game dishes of wild boar and rabbit in Florence, you’re more likely to enjoy seafood and fragrant pesto dishes on the Ligurian coast. 

Nevertheless, there are certain Italian traditions you just won’t be able to shake, no matter which part of the country you visit; gelato on a hot summer day, the simple genius of antipasto and the social rituals of an evening aperitivo once the sun begins to set. Italy is also the birthplace of the slow food movement, placing central importance on 0km, local, seasonal produce and high-quality ingredients. Why not stay in one of our villas that champion farm-to-table produce; where you can see from your private pool what you’ll be eating on your private terrace that evening, where the wine you drink comes from the vineyards on your doorstep. 

At our fully staffed villas with chefs you can have a local cook or professional chef prepare delicious classic Italian dishes for you in your villa kitchen or even teach you recipes in a hands-on cooking class. True gastronomes can also enjoy an all-inclusive cooking vacation and spend a week learning the secrets behind some of Italy’s best recipes. 

A vacation in Italy would not be complete without good wine either; from seductive reds like Valpolicella, Brunello di Montalcino and Chianti Classico to crisp white and sparkling wines like Prosecco, Gavi di Gavi, Soave and Pinot Grigio. From our luxury villas in Italy, you can explore the very regions where these wines are produced, enjoy private sommelier-led wine tastings in your villa kitchen and tour prestigious wineries. We are also the only villa rental service to offer an all-inclusive wine vacation, keeping your villa wine cellar topped up with your favourite labels for the duration of your stay. 

Shopping 

Italy is a country with an incredibly versatile shopping scene; whether you are a true fashionista with an eye for designer brands, love to hunt out vintage and antique treasures or are purely in it for the food and wine. 

Italy is the birthplace of fashion powerhouses like Prada, Valentino, Bulgari, Fendi and Gucci… we could go on. If haute couture is more your style, Italy is home to not one but two fashion capitals, Rome and Milan. The latter makes for a great day trip from our villas near Venice and Verona. Of course, some of the biggest names in luxury fashion can be found in Venice as well, just head for Salita S. Moise and Calle Larga XXII Marzo near Piazza San Marco.

Florence is another great city for shopping, whether you are looking for high street styles or vintage gems. For designer brands without eye-watering price tags, be sure to see our guide to designer outlets near Florence. The Oltrarno district is also a great starting place to find unique artisan momento, like Italian leather and paper. Tuscany and Umbria are also large producers of Italian ceramics, which you’ll find in plenty of the smaller hill-towns like San Gimignano, Montelupo Fiorentino and Cortona. 

A trip to Italy would not be complete without paying a visit to one or two farmers markets either. Read our guide to farmer’s markets in Tuscany and Umbria for everything from organic honey and extra-virgin olive oil to the best places to find antiques. If you are staying in one of our villas near Venice or Verona, Padua is the city to visit. Markets are held daily in the Piazza delle Erbe and Piazza della Frutta, and every Saturday in the Prato della Valle, selling flowers, seasonal fruits and vegetables, as well as herbs and spices. 

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Showing: 120 villas

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 9

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

Top-level luxury villa facing Orvieto with staff & cook. Large, private pool & gym. Contemporary A/C interiors, luxury bathrooms & professionally equipped kitchen. Grounds with panoramic outdoor living & dining areas. Breakfast & dinner service included in the price. 

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€ 19,530
€ 31,801
$ 21,681
$ 35,304
£ 16,550
£ 26,950

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

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

Elegant villa with private heated pool surrounded by olive groves near Vinci. Minimal design using exquisite materials. A/C bedrooms & luxurious ensuite bathrooms. Terrace & outdoor dining area facing sunset with magical views.

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€ 11,935
€ 17,419
$ 13,250
$ 19,338
£ 10,115
£ 14,762
New villa, be the first to review

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Elegant villa with private heated pool surrounded by olive groves near Vinci. Minimal design using exquisite materials. A/C bedrooms & luxurious ensuite bathrooms. Terrace & outdoor dining area facing sunset with magical views.

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€ 13,644
€ 20,442
$ 15,147
$ 22,694
£ 11,562
£ 17,324
New villa, be the first to review

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

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€ 5,214
€ 8,866
$ 5,788
$ 9,843
£ 4,419
£ 7,513

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

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€ 5,876
€ 10,034
$ 6,524
$ 11,140
£ 4,980
£ 8,504

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 10

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Large villa & guest house with a private pool, air-con bedrooms all with ensuite bathrooms near Montepulciano. Very spacious, lovely sitting areas. Gorgeous garden with a beautiful dining loggia.

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€ 6,933
€ 11,890
$ 7,697
$ 13,199
£ 5,875
£ 10,076

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7

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

Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and Chef service for 6 breakfast is also included in the price.

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€ 7,895
€ 12,287
$ 8,765
$ 13,641
£ 6,691
£ 10,413

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 8

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

Spacious 16C stone farmhouse with air-conditioned bedrooms and a private pool on the edge of the Chianti. Comfortable homey interiors with many nooks, three kitchens and chef service for 6 breakfast included in the price.

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€ 8,504
€ 13,232
$ 9,441
$ 14,689
£ 7,207
£ 11,213

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Picturesque stone farmhouse on a hill top with sweeping views of the countryside near to Siena. Private pool & pool house. modern outside lounging area and air conditioned bedrooms

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€ 6,696
€ 10,645
$ 7,433
$ 11,818
£ 5,674
£ 9,022

SLEEPING: 18 - BEDROOMS: 11 - BATHROOMS: 7

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Picturesque stone farmhouse on a hill top with sweeping views of the countryside near to Siena. Private pool & pool house. modern outside lounging area and air conditioned bedrooms

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€ 7,973
€ 13,009
$ 8,852
$ 14,442
£ 6,757
£ 11,024

SLEEPING: 12 - BEDROOMS: 7 - BATHROOMS: 6

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17th-century farmhouse & guesthouse on a hilltop 5km from Greve in Chianti. Private pool & Chianti views. Interior has beamed ceilings, terracotta floors, A/C bedrooms & modern bathrooms. Ideal location to explore Tuscany.

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€ 5,006
€ 10,012
$ 5,558
$ 11,115
£ 4,242
£ 8,485

SLEEPING: 16 - BEDROOMS: 11 - BATHROOMS: 9

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17th-century farmhouse & guesthouse on a hilltop 5km from Greve in Chianti. Private pool & Chianti views. Interior has beamed ceilings, terracotta floors, A/C bedrooms & modern bathrooms. Ideal location to explore Tuscany.

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€ 7,093
€ 14,183
$ 7,875
$ 15,746
£ 6,011
£ 12,020

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.

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€ 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.

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€ 11,116
€ 14,023
$ 12,340
$ 15,568
£ 9,420
£ 11,884

New for 2025

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Serene hilltop villa 10km from Grosseto with 17m infinity pool overlooking vineyards. Seamless indoor/outdoor living between alfresco dining areas. Ideally located on organic wine estate near Tuscany’s best beaches. Complimentary wine tasting & tour.

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€ 10,945
€ 12,275
$ 12,151
$ 13,627
£ 9,276
£ 10,402
New villa, be the first to review

SLEEPING: 6 - BEDROOMS: 4 - BATHROOMS: 4

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

Charming hilltop retreat with stunning views near the Tuscan coast. Private swimming pool, hot tub & Recently fitted private spa with a second hot tub [extra fees apply]. Air-con bedrooms, loggia for al fresco dining.

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€ 3,701
€ 6,606
$ 4,109
$ 7,333
£ 3,136
£ 5,598

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

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

Charming hilltop retreat with stunning views near the Tuscan coast. Private swimming pool, hot tub & Recently fitted private spa with a second hot tub [extra fees apply]. Air-con bedrooms, loggia for al fresco dining.

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€ 3,875
€ 7,014
$ 4,302
$ 7,787
£ 3,284
£ 5,944

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

Charming hilltop retreat with stunning views near the Tuscan coast. Private swimming pool, hot tub & Recently fitted private spa with a second hot tub [extra fees apply]. Air-con bedrooms, loggia for al fresco dining.

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€ 4,624
€ 8,499
$ 5,133
$ 9,435
£ 3,918
£ 7,203

SLEEPING: 2 - BEDROOMS: 1 - BATHROOMS: 1

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

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€ 2,001
€ 3,971
$ 2,221
$ 4,408
£ 1,696
£ 3,365

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

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€ 2,193
€ 4,395
$ 2,434
$ 4,879
£ 1,858
£ 3,725

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

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€ 2,382
€ 4,820
$ 2,645
$ 5,351
£ 2,019
£ 4,084

Why stay in Italy 

Every traveller is different, so there is no such thing as the “best” villa in Italy; only the best Italian holiday rental for you. When you contact Tuscany Now & More, you will talk to someone who has stayed at the villas which interest you. It’s our golden rule — and why we stick to a focused, specialist portfolio of around 139 handpicked villas.

Italy is one of the most important centres for the arts, literature, music, philosophy and religion. It has produced some of the world's greatest intellectuals, humanists and artists like Dante, Galileo Galilei, Raphael and Michelangelo. It is a country with over 20 national parks and countless itineraries for hiking and cycling. Italy has a varied natural landscape, from dramatic alpine climbs and glamorous Italian lakes, brightly coloured fishing villages and protected coastlines, to ancient woodlands and sweeping valleys. It is also a country with a deep connection to the land, respecting family traditions and recipes stretching back generations. Great food, wine, plenty of history and art, beautiful surroundings; what’s more to want? 

Perhaps your idea of the perfect vacation in Italy starts with an early morning stroll into a nearby town or village for freshly baked bread and a strong cup of coffee, perhaps it is a week sunbathing by your enormous private pool or sampling fine wines surrounded by your private vineyard. Whether you want to be right in the heart of Florence, tasting your way through all the regional delicacies of Umbria, deep in the heart of Chianti or exploring the great outdoors near Padua; speak to our concierge today and discover your own Italy. 

When to visit Italy 

Spring temperatures are pleasant throughout most of Northern and Central Italy, with average daytime highs of 23℃ (73℉) and lows of 12℃ (53℉) overnight. It is the season of Carnevale and Easter celebrations throughout the country, which is a vibrant and unique way to experience Italy if you can handle crowds. However, it is also much quieter and more temperate than peak season, making it a great time to visit more popular cities like Florence, Venice and Rome. 

Summer is high season across Italy and average daytime highs can range from 28℃ (82℉) in Venice to 31℃ (88℉) in Rome, with lows between 17 ℃ (66℉) and 19℃ (66℉) overnight. This is the season for relaxing by your private pool, day-tripping to the Tuscan or Ligurian Coast for light seafood lunches and luxurious sea breezes, and for enjoying an unforgettable evening aperitivo in your favourite historic piazza. 

Autumn in Italy is the season for outdoor lovers — average daytime highs in Fall can still reach 22℃ (71℉) with overnight lows of 11 °C (52 °F) well into October, making it the perfect temperature for hiking and cycling. 

Winter is also a great time to visit Italy, even if it’s just for the magic of Christmas in a majority Catholic country or to make the most of the empty art galleries and museums like the Uffizi and Vatican. Expect daytime highs of 12 °C (54 °F) and overnight lows of 4 °C (40 °F).

For more ideas on the best time to visit Italy, read our month-by-month guides to Tuscany, Umbria and Veneto. 

About Our Handpicked Villas in Italy 

All of our villas at Tuscany Now & More are locally owned and staffed, and we take pride in being able to offer each of our guests a unique experience tailored to their needs. If you are interested in learning more about what makes us different, you can read the Tuscany Now & More story.

Concierge service

Everyone renting a villa in Italy with Tuscany Now & More gets free, unlimited access to our renowned concierge service. If you want shopping stocked in your fridge on arrival, or a private chef to cook dinner for a special occasion, just ask. Making your holiday lettings extra-special is part of our service. While you are in Italy, our 24-hour ground staff are available by phone or WhatsApp.

Checking in & out

You should check-in at your Italian holiday rental between 4pm and 7pm. 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 10am on the last day of your holiday rental. The villa owner or caretaker will arrive at 9am 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 before your arrival. Some holiday villas have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with 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 Italian holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and changes can be organised via our concierges.

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