Villa rentals in Tuscany

Few places in the world have a WOW factor quite like Tuscany. Whether it’s a silent sunrise in the emerald-green expanse of the Val d’Orcia; lunch on the terrace of your Tuscany holiday rental overlooking vines and olive groves; or the milky-pink sunset of a Chianti spring… At any time of day or year, renting a villa in Tuscany is an experience like no other.

At Tuscany Now & More we take pride in our service. We have 30 years’ experience matching every guest to just the right villa. Someone from our small team visits or stays in every 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 Tuscany’s best villa company.)

Almost all our villas in Tuscany have air-conditioned bedrooms — which you’ll appreciate in the hot Tuscan summer — and many have air-conditioning throughout. 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 Tuscan 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 Tuscany

History left its mark across this region, in the Renaissance art of Florence and the medieval brick palaces of Siena. Michelangelo, Leonardo Da Vinci, Gucci, Puccini and St. Catherine of Siena are just a handful among of hundreds of famous Tuscans. You can visit their many sights and shrines from several Tuscany holiday rentals.

Older, pre-Roman Etruscan heritage is preserved in museums and tombs, and even the landscapes, of Volterra and the Maremma, including at a UNESCO World Heritage Site near Tarquinia, in neighbouring Lazio.

All of these — and many more fascinating places, first-rate wineries and spectacular landscapes — are within easy range of our vacation rentals and luxury villas in Tuscany.

What to Do in Tuscany

Art and architecture; food and drink; the stone streets and scenery of a hilltop town — these are the mainstays of any itinerary from our luxury villas in Tuscany.

From the medieval period to the Renaissance, Tuscany led Europe in art and architecture. In Florence, Lorenzo Ghiberti’s Gates of Paradise and Brunelleschi’s cathedral dome face each other across Piazza del Duomo. Michelangelo, Botticelli, and Leonardo da Vinci were all Tuscans, and left works across the region, many now in Florence’s Uffizi Gallery.

Pisa’s glory days were earlier, during the Romanesque period. The city is now famous for a bell tower that went wrong. We call it the Leaning Tower of Pisa — though its architect would likely have been embarrassed, not proud, to hear that! Pisa is a favourite daytrip from many of our villas for families.

Siena’s style is Gothic, in the architecture of its shell-shaped Campo (main square) and on the frescoed walls of its Palazzo Pubblico. The nearby village of San Gimignano is another immaculately preserved Gothic relic.

Tuscany’s scenery is just as good from two wheels. Cycling or e-biking is a great way to explore the back-roads of the Chianti around Radda, or the photogenic clay landscapes of the Crete Senesi, south-east of Siena.

Food and Drink in Tuscany

Tuscan ingredients speak for themselves. Flame-grilled beef from the Chianina breed of cattle makes an authentic bistecca alla fiorentina. Simple dishes like panzanella (a salad of bread, tomato, olive oil and basil) or pasta ribbons tossed with a wild-boar ragù are elevated by Tuscany’s incredible seasonal produce. Truffles are abundant, in season, if you fancy a treat. Many of our villas in Tuscany offer truffle hunting trips.

Tuscany is one of the world’s great red wine regions. Brunello di Montalcino, Vino Nobile di Montepulciano, and Chianti Classico are produced within growing zones where quality is strictly controlled by DOCG (Denominazione di Origine Controllata e Garantita) rules. The Maremma’s Morellino di Scansano is another robust red pressed from the native Sangiovese grape.

Shopping in Tuscany

Wine and olive oil are sold almost everywhere. Extra-virgin olive oils are especially good in the Chianti, the hills close to Pisa and around Monte Albano, west of Florence. All Tuscany’s best red wines, as well as the sticky-sweet Vin Santo and many niche Tuscan wines, age well and can be cellared.

Several Tuscan towns have strong artisan traditions. Painted majolica ceramics have been made in the Valdarno, west of Florence, for centuries. Cortona and Colle Val d’Elsa both have excellent ceramic workshops. Impruneta is the home of Tuscan terracotta. Volterra has an alabaster heritage stretching back to the Etruscans.

Leather manufacture is a Florentine tradition. Although lots sold in city shops and markets is imported, the Scuola del Cuoio trains the next generation of artisans and sells their hand-made wares. Our guide to buying leather in Florence will help you find the best.

After Milan, Florence is Italy’s second city for fashion. There’s plenty of high-toned shopping for designer threads along Florence’s Via de’ Tornabuoni. Florence is also the home of internet fashion sensation Luisa Via Roma. The Mall outlet, east of Florence, sells end-of-line items from top-end Italian couture brands at discounted prices, including by the famous “Florentine Four” fashion designers: Gucci, Pucci, Cavalli and Ferragamo.

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Showing: 91 villas

SLEEPING: 15 - BEDROOMS: 8 - BATHROOMS: 7

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

Luxury stone farmhouse in Chianti with staff & cook. Private infinity pool, multiple alfresco living spaces & large A/C bedrooms with luxurious ensuite bathrooms. On-site concierge. Breakfast & dinner service included. 

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€ 10,647
€ 15,774
$ 11,820
$ 17,512
£ 9,023
£ 13,368

SLEEPING: 15 - BEDROOMS: 8 - BATHROOMS: 7

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

This rental option new for 2019 at Il Cortile Pratolino includes traditional or vegetarian cooking lessons & food experiences, alongside the chef & staff who will prepare breakfast and evening meals included in the rental price.

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€ 16,004
€ 21,131
$ 17,767
$ 23,459
£ 13,562
£ 17,907

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 7

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

Luxury stone farmhouse set on a large estate amid vineyards & olive groves near Florence. Fantastic kitchen, air-con bedrooms, en suite bathrooms. Large private fenced pool, hot tub, sauna, spa, yoga deck and yoga studio with gym. Access to the Estate's private tennis court.

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€ 16,454
€ 20,679
$ 18,267
$ 22,957
£ 13,944
£ 17,524

New for 2025

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 7

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

Fully-staffed family villa within hamlet 12km from Siena. Modern A/C bedrooms & ensuite bathrooms. Historic, peaceful setting with private, gated pool & manicured gardens with olive groves. Breakfast & dinner service included in the price. 

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€ 9,327
€ 14,108
$ 10,354
$ 15,663
£ 7,904
£ 11,956
New villa, be the first to review

New for 2025

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 7

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

Fully-staffed family villa within hamlet 12km from Siena. Modern A/C bedrooms & ensuite bathrooms. Historic, peaceful setting with private, gated pool & manicured gardens with olive groves. Breakfast & dinner service included in the price. 

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€ 10,969
€ 17,580
$ 12,178
$ 19,517
£ 9,296
£ 14,898
New villa, be the first to review

New for 2025

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 5

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

Design-led luxury villa near San Gimignano. 18m heated infinity pool, sauna & summer kitchen. Minimalist Wabi Sabi interiors in a converted medieval church. All ensuite bathrooms. Private hilltop position with 180° views

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€ 13,194
€ 17,500
$ 14,648
$ 19,428
£ 11,182
£ 14,831
New villa, be the first to review

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

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

Stylish 16th-century luxury villa in Chianti with staff & cook. Terraced garden with outdoor living & dining areas. Private heated pool, gym & wellness area with treatment room and sauna [wellness area services available to those purchasing treatments]. Elegant interiors, internal lift & A/C in all rooms. On-site concierge. Breakfast & dinner included in the rental price.

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€ 12,018
€ 18,084
$ 13,342
$ 20,077
£ 10,185
£ 15,326

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.

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€ 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.

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€ 9,580
€ 17,961
$ 10,635
$ 19,940
£ 8,118
£ 15,221

Special Christmas & New Year Offer

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.

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€ 7,776
€ 11,870
$ 8,633
$ 13,178
£ 6,590
£ 10,059

Special Christmas & New Year Offer

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.

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€ 8,190
€ 13,007
$ 9,092
$ 14,440
£ 6,941
£ 11,023

Special Christmas & New Year Offer

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.

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€ 10,238
€ 16,258
$ 11,365
$ 18,050
£ 8,676
£ 13,778

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.

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€ 4,822
€ 10,089
$ 5,354
$ 11,200
£ 4,087
£ 8,550

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. 

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€ 8,930
€ 14,196
$ 9,914
$ 15,760
£ 7,568
£ 12,031

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 with two family suites, perfect for younger families. Wealth of alfresco living areas. On-site attentive staff can prepare meals & offer cooking lessons.

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€ 5,787
€ 12,106
$ 6,424
$ 13,440
£ 4,904
£ 10,260

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.

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€ 9,895
€ 16,214
$ 10,985
$ 18,000
£ 8,385
£ 13,741

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

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

Large, elegant farmhouse & guest house with a private pool near Florence. Air-con bedrooms in main house. Modern bathrooms. lovely garden and spectacular views. Shaded terrace ideal for al fresco meals.

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€ 5,096
€ 8,301
$ 5,657
$ 9,215
£ 4,318
£ 7,034

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 7

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

Large, elegant farmhouse & guest house with a private pool near Florence. Air-con bedrooms in main house. Modern bathrooms. lovely garden and spectacular views. Shaded terrace ideal for al fresco meals.

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€ 6,361
€ 11,791
$ 7,062
$ 13,090
£ 5,391
£ 9,992

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 7

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

Plan a wedding for up to 60 guests in the Mugello countryside, 40km from Florence. A spacious converted farmhouse with wrap-around gardens & terrace, large private pool, A/C bedrooms, professional kitchen for events. Chapel within walking distance. Chef services included for arrival dinner & Sunday breakfast.

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€ 7,716
€ 13,431
$ 8,566
$ 14,910
£ 6,539
£ 11,382

SLEEPING: 20 - BEDROOMS: 10 - BATHROOMS: 7

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

This rental option includes fantastic local chefs who will prepare a pizza dinner upon arrival, breakfast for seven days and three dinners during the week. Cost of ingredients and drinks is not included. 

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€ 10,052
€ 15,482
$ 11,160
$ 17,188
£ 8,519
£ 13,120
Rental options (size of party):

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 9

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

Restored luxury stone farmhouse & guesthouse with private heated infinity pool in Siena outskirts. Interior has terracotta floors, beamed ceilings, A/C in all rooms & en-suite bathrooms. Plenty of panoramic outdoor living & dining areas. Private gym.

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€ 11,383
€ 15,676
$ 12,637
$ 17,403
£ 9,646
£ 13,285

Where to Stay in Tuscany

Every traveller is different, so there is no such thing as the “best” villa in Tuscany; only the best Tuscan 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 maintain a small, specialist portfolio of around 139 handpicked villas.

Maybe a villa with a pool is an essential, or a villa with air conditioning, or even one of our fully staffed villas in Tuscany. To work out where to stay in Tuscany, ask yourself six questions...

Are you a first-time visitor? Florence, Tuscany’s capital, has the largest concentration of sights and things to see and do. The Chianti, hills to the south of Florence and within easy reach of the city, is one of the most famous wine zones in the world. It makes sense to base yourself around here if you are renting a villa in Tuscany. You can easily mix city with countryside. If you have an idea of “classic Tuscany” embedded in your mind, you will find it in around our Chianti villas.

Do you need a dose of culture? For museums and other cultural spots, consider renting a villa in Tuscany within easy range of Florence or Siena (or between them, in the Chianti hills). Florence has the Uffizi Gallery; Michelangelo’s “David”; Medici villas, palaces and tombs; Renaissance gardens; countless painted chapels and more. Siena’s sights include the Campo, Palazzo Pubblico and Duomo, each of them unchanged since medieval times. Another location for culture vultures renting a villa in Tuscany is Lucca, birthplace of the composer Puccini, with a museum and summer opera festival dedicated to him. You should also see our collection of villas near Pisa and Lucca.

Do you want a holiday rental close to a village? Many of our vacation rentals are within walking distance of a village or town centre. Staying in one of our Tuscany villas near villages will connect you with small-town Tuscan life. You can stroll up the road for a cappuccino in the town square, or buy freshly baked bread each morning. Eat with the locals at the village trattoria. In the evenings, you can enjoy pre-dinner aperitif or a lively night in the town bar with no need to drive home. You get a special view of Italy: the local angle.

Are you a returning visitor looking for a new experience? You’ve seen a Chianti sunset, met David’s inscrutable gaze at the Accademia, climbed the Leaning Tower of Pisa, and walked Siena till your feet are sore. But you still haven’t seen all a villa in Tuscany has to offer — not even close. At a villa in the Maremma, you can explore the rolling hills of the Morellino winelands and archaeological sites of the ancient Etruscans. North of Florence, the Mugello was the original home of the Medici family, who ruled over Renaissance Florence. A villa near Borgo San Lorenzo puts you right at the heart of this very different part of Tuscany.

Do you have special interests to pursue? If you are a wine lover, it makes sense to choose a Tuscany holiday rental in the Chianti, or one of our luxury villas near Montepulciano. If you have a passion for ancient history, our Maremma villas are in the heartland of the Etruscan world (aka “Etruria”). Their fascinating pre-Roman culture left important archaeological remains (Vetulonia, Populonia, Roselle) and museums stuffed with artefacts (Grosseto, Volterra, Chiusi). Outside Pitigliano, the Etruscans carved a network of vie cave (open-air passages) into the soft tufa rock. Their use? That — like much of Etruscan life — remains a mystery.

Did you know Tuscany has a seaside? If you are undecided between a villa with a pool and a house by the sea, our select collection of beach villas in Tuscany means you don’t have to choose. Tuscany’s 250 miles of coastline stretches from flat, family-friendly sands and fashionable resorts in the north, to the rocky shores, remote dunes and fishing ports of Monte Argentario and the southern Maremma — “Tuscany for the cognoscenti”, The Guardian called it. All our luxury beach villas have private swimming pools, air-conditioned bedrooms (some are fully air-conditioned throughout), and free use of our renowned concierge service.

When to Visit Tuscany

Spring temperatures are pleasant over most of Tuscany. You can expect an average daytime high of 23℃ (73℉) and a low of 11℃ (51℉) overnight. Easter weekend is busy in Florence for the folklore Easter Day tradition, the Scoppio del Carro (Explosion of the Cart). This festival features 150 white oxen, an antique cart filled with fireworks, and a very big bang.

Summer in Tuscany is high season. The daytime temperature rises to an average high of 30℃ (86℉), with 17℃ (62℉) overnight typical. This is the ideal season for relaxing by your private pool. Cultural festivals happen outdoors all summer, from the Palio di Siena horserace to the open-air Puccini Festival, with live opera beside the composer’s lakeside home near Lucca.

Despite cooler temperatures, autumn and winter in Tuscany are still lots of fun. The sun shines on most days, with an average daytime high of 13℃ (55℉) and a low of 4℃ (39℉) overnight. Low season means you can enjoy Tuscany’s cities at your own pace. You can easily find a table at restaurants like La Bottega del Buon Caffè in Florence, Bistrot in Forte dei Marmi, and Osteria di Passignano in the Chianti hills. Make sure to try the seasonal delicacy, truffles.

About Our Handpicked Villas in Tuscany

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

Checking in & out
You should check in at your Tuscany 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 any outstanding payments. If you want to depart earlier, you can 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 holiday rentals include bed linens, bathroom and swimming pool towels for the number of guests. These are provided weekly. Extra services and changes can be organised with our concierges.

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