Exclusive Seaside Estate With Private BeachN°001
Italy (other), Italy
Private PoolSpa
From $55,041 per night
Tuscany is central Italy's storied region of cypress-lined hills, vineyards and Renaissance cities. Renting a luxury villa here places you among olive groves and historic estates, with the privacy of a private pool, the space for families or groups, and concierge ease within reach of Florence and Siena.
- Curated luxury villas with private pools set among olive groves and vineyards
- Easy reach of Florence, Siena and the Chianti wine route
- Renaissance art, UNESCO-listed city centres and Michelin-level dining
- Concierge service and direct booking with Smiling House
- Coastal escapes nearby at Forte dei Marmi and along the Tuscan shore
Known forRenaissance art, rolling vineyard landscapes, Chianti wine, hilltop towns and historic stone villas
Best time to visitMay to June and September to October for warm weather, the harvest and fewer crowds
Nearest airportFlorence Airport (FLR) and Pisa International Airport (PSA)
Ideal forCouples, families and groups seeking culture, food, wine and countryside privacy
Unique luxury villa with direct access to the seaN°002
Cala Moresca, Italy
Sea ViewWaterfront
From $24,919 per night
Luxury Tuscan Escape With Pool ViewsN°003
Italy (other), Italy
Private poolHot TubSauna
From $14,936 per night
Luxe Tuscan Villa Near The Historic Area Of LuccaN°004
Tuscany, Italy
From $12,314 per night
Scenic Chalet With Rustic SophisticationN°005
Italy (other), Italy
Hot TubSaunaFireplace
From $11,627 per night
Stunning Italian Villa With Great Mountain ViewsN°006
Tuscany, Italy
Private Pool
From $11,512 per night
420homes available
1–18bedrooms
up to 36guests
202with a pool
Events not to miss in Tuscany
- 2 July and 16 August
Palio di Siena
Siena's famous bareback horse race turns the shell-shaped Piazza del Campo into a cauldron of contrada rivalry twice each summer. Watch from a reserved balcony, then retreat to the quiet of a countryside villa.
- June to July
Lucca Summer Festival
International headline acts perform inside Lucca's Renaissance walls across several weeks of open-air concerts. An easy evening out from villas in the hills between Lucca and Pisa.
- February to early March
Carnevale di Viareggio
One of Europe's great carnivals, with vast satirical papier-mâché floats parading along the Versilia seafront. A colourful reason to visit Tuscany out of season.
- June and early September
Giostra del Saracino, Arezzo
Arezzo's medieval jousting tournament fills Piazza Grande with costumed processions, drummers and mounted knights tilting at the Saracen. Held twice a year, it pairs well with the city's famous antiques fair.
- September
Expo del Chianti Classico, Greve
The Chianti hills celebrate the new vintage with tastings from dozens of estates in Greve's main square. Time a harvest-season villa stay around it and follow up with private cellar visits.
Tuscany through the seasons
- Spring (March – May)
Wildflowers and uncrowded hill towns
Poppies and irises colour the Val d'Orcia while Florence and Siena are still calm. Mild days suit cycling, garden visits and long lunches on the villa terrace.
- Summer (June – August)
Pool season and festival evenings
Hot, dry days made for a private pool among the vines, with the Palio, open-air opera and village sagre filling the evenings. Book early, this is peak villa season.
- Autumn (September – November)
Grape harvest and white truffles
The vendemmia sweeps through Chianti and Montalcino, then San Miniato's white truffle season begins. Golden light, warm days and superb eating make this many regulars' favourite time.
- Winter (December – February)
Quiet cities and new olive oil
Florence's museums empty out, frantoi press the new oil and villa fireplaces come into their own. A slow, gastronomic take on Tuscany at its most local.
The Area
Tuscany unfolds across central Italy as a landscape of terracotta hilltowns, silver olive groves and ordered vineyards stitched together by winding, cypress-lined roads. Florence, the cradle of the Renaissance, flourished under Medici patronage and gave the world Botticelli, Leonardo da Vinci and Michelangelo, whose work still fills its churches and galleries. Siena, with its shell-shaped Piazza del Campo, preserves a medieval character all its own. Beyond the cities lie the gentle Val d'Orcia, the Chianti hills and quieter corners such as Cinigiano and Monticchiello. The Italian language itself evolved from the Tuscan dialect spoken near Florence, a measure of the region's cultural weight. It is the Italy most travellers picture when they imagine a luxury escape.
Where to Stay in Luxury Villas in Tuscany
Smiling House offers a curated collection of luxury villas in Tuscany, from restored stone farmhouses with private pools to elegant country estates surrounded by their own vineyards. The Chianti hills between Florence and Siena suit those who want vineyards and easy city access, while the Val d'Orcia near Monticchiello and the Maremma around Cinigiano reward travellers seeking deep countryside calm. For sea and style, Forte dei Marmi on the Versilia coast pairs sandy beaches with refined shopping. Many properties combine generous gardens, alfresco dining terraces and space for families or groups, with concierge support arranging chefs, drivers and tastings. Booking direct keeps the experience personal from first enquiry to arrival.
Things to Do
Begin in Florence at the Cattedrale di Santa Maria del Fiore, the great marble-fronted Duomo begun in 1296, whose cathedral, baptistery and Giotto's bell tower anchor a UNESCO World Heritage centre. Wander the Uffizi, cross the Ponte Vecchio, then drive south into Chianti for cellar visits and tastings. Siena's Palio horse race and Arezzo's Giostra del Saracino joust bring centuries-old pageantry to life, while Montepulciano's Bravio delle Botti sees teams roll wine barrels uphill. Cycle through the Val d'Orcia, soak in the thermal springs near Bagno Vignoni, or simply linger over long lunches on a villa terrace as the hills shift through shades of gold.
Dining and Nightlife
Tuscan cooking is rustic and generous, built on bread, beans, olive oil and slow-cooked meats. Seek out dishes such as pici con cacio e pepe, ribollita, bistecca alla Fiorentina and truffle menus in autumn. The best tables are often the osterie where locals eat, away from the main tourist streets and picture menus. In Siena, Osteria Le Logge near the Piazza del Campo occupies a former nineteenth-century pharmacy, its shelves now lined with wine. After dark, the region's joie de vivre carries on in piazza wine bars, vineyard dinners and the polished lounges of Forte dei Marmi, where the Versilia coast keeps its glamour late into the night.
When to Visit and Getting There
Late spring, from May into June, brings warm days and green hills, while September and October align with the grape and olive harvests and softer light. July and August are hot and busy, ideal for villas with pools and coastal access. Winter is quiet and atmospheric, with truffle season and uncrowded museums. Florence Airport (FLR) is closest to the centre and Chianti, while Pisa International Airport (PSA) serves the coast and works well for Forte dei Marmi. Both connect to major European hubs. A hire car is essential for exploring the countryside and reaching hilltop villas, and high-speed trains link Florence to Rome and Milan in a few hours.