Tuscany
Rolling hills, serious wine, and villas that have been hosting guests for centuries.
Price Range
£1,500 - £5,000
per night
Best Months
May, June, September, October
Best For
Families, Couples, Multi-generational, Foodies
Properties
3 listed
Tuscany invented the luxury villa rental. While other destinations were still building hotels, Tuscan landowners were converting medieval farmhouses into properties that make five-star resorts feel generic. The tradition runs deep, and it shows in the quality of the stock.
The Chianti Classico zone between Florence and Siena remains the core market. Here, GBP 10,000-25,000/week buys a restored podere with original frescoes, a private vineyard, and views that haven't changed since the Renaissance. Val d'Orcia to the south offers a wilder, more photogenic landscape at slightly lower rates. The Lucca hills provide Pisan coast access with a countryside setting.
What separates Tuscany from beach destinations is the depth of the experience. A week here involves private wine tastings at estates that don't open to the public, cooking classes with ingredients from your villa's garden, and day trips to Florence and Siena that don't require a hotel change. The villa is base camp for a cultural immersion, not just a place to sleep.
Tuscany
Highlights
Medieval estates converted to world-class private villas
Private vineyard and winery access unavailable to hotel guests
Florence, Siena, and Pisa within day-trip range
Professional Italian cooking and culinary experiences
Val d'Orcia UNESCO landscape without the tourist crowds
Getting There
Florence Airport (FLR) and Pisa Airport (PSA) both serve the region, with Pisa offering more low-cost options and Florence better connections to premium carriers. Rome Fiumicino (FCO) is 2.5-3 hours by car. Most luxury villas arrange private transfers. A hire car is strongly recommended for exploring the region - distances between towns are short but public transport is limited.
Insider Tip
September harvest season is peak Tuscany. The vendemmia (grape harvest) happens in the vineyards surrounding your villa, temperatures are perfect, and summer crowds clear after the first week. Many estate villas offer private harvest experiences exclusively to their rental guests.
Tuscany
Available properties
3 luxury villas from £1,500/night
Villa Il Falconiere
A 14th-century Cortona hilltop estate producing its own Syrah and olive oil.
Podere San Lorenzo
A restored farmstead in the Val d'Orcia, where cypress-lined roads meet rolling wheat fields.
Villa Montalcino
A Brunello wine country retreat ten minutes from Montalcino's medieval centre.
Vetted Agents
Tuscany specialists
Agents who know the local market, have inspected properties, and provide concierge-level service.
Azure Luxury Villas
Est. 2009 · 85 properties
Specialists in Mediterranean luxury villa rentals with over 15 years of experience across Spain, France, and Italy. Azure hand-picks every property and conducts annual inspections. Their concierge team handles everything from airport transfers to private chef bookings, and they maintain relationships with the best local service providers in each destination.
Mediterranean Estates
Est. 2015 · 35 properties
A boutique agency specialising in historic estates and countryside villas across Tuscany and the Amalfi Coast. Mediterranean Estates focuses on properties with character - restored farmhouses, clifftop palazzos, and vineyard estates. They excel at sourcing properties that are not listed anywhere else, drawing on decades of local relationships.
FAQ
Tuscany villa rental FAQs
Do Tuscan luxury villas include private chef services?
Most properties at the GBP 1,500+/night level offer private chef services, either included or as an optional extra at EUR 400-800/day depending on the number of guests and meal complexity. Many chefs will shop at local markets with you before cooking. Some estates have resident chefs who know the property kitchen and local suppliers intimately.
Is a car necessary when renting a villa in Tuscany?
Yes, almost without exception. Tuscan villas are rural by nature, and restaurants, towns, and attractions require driving. Most agents can arrange luxury car hire (Mercedes, BMW, or classic Fiat 500 for fun). Roads are well-maintained but narrow in places. Some villas offer chauffeur services as an alternative.
What is the difference between Chianti and Val d'Orcia for villa rentals?
Chianti is closer to Florence and Siena (30-45 minutes), more wooded, and has the strongest restaurant and wine-tasting infrastructure. Val d'Orcia is further south, more dramatically photogenic (the classic cypress-lined road shots), quieter, and 15-25% cheaper at equivalent quality. Chianti suits culture-focused trips; Val d'Orcia suits pure relaxation.