Curated Luxury Properties · Tuscany · 10 Stays
Luxury Villas in Tuscany, Italy
Tuscany remains Italy's most complete luxury villa destination, pairing Chianti vineyard estates around Castellina in Chianti and Radda in Chianti with the coastal ease of Forte dei Marmi. Inland, the rolling farmland near San Quirico d'Orcia and the Province of Grosseto suits longer, slower stays, while Florence and Pisa put art and history within easy reach. Late spring and early autumn bring the best light and fewer crowds than the height of summer.
Browse 10 stays →10 properties in Tuscany
No paid placements · Rated by our team
10 properties
Editor picks
“The documented De' Medici provenance sets this apart from other luxury Tuscan rentals, offering guests the rare opportunity to stay in a property with genuine Renaissance aristocratic history. The original ballroom, now converted to a grand lounge with the period fireplace intact, creates an experiential connection to Italy's noble past that most estates cannot replicate. Unlike typical large villas that feel like expanded holiday homes, Midnight Ball maintains the spatial grandeur and formal entertaining capability it was designed for, with a banquet-worthy dining room and wine cellar that support true estate-style hospitality. The combination of 20 bedrooms across multiple buildings with extensive grounds creates privacy options rare even among large Tuscan properties, allowing different groups within a party to find their own space whilst maintaining connection to the communal areas.”
“Villa Oblò occupies one of the most coveted positions in Forte dei Marmi, where you can walk to the beach in under three minutes yet enjoy complete privacy within extensive Mediterranean gardens. The villa's contemporary architecture incorporates traditional Tuscan materials with unexpectedly sophisticated amenities, including a dedicated spa treatment room and rooftop terrace that most comparable properties lack. Unlike many coastal villas that compromise on either beach proximity or garden space, Villa Oblò delivers both: the sound of the sea reaches the property whilst mature landscaping creates complete seclusion. The outdoor dining terrace with its traditional pizza oven and hydromassage pool creates an authentic Tuscan entertaining experience that extends well into the evening, something most rental properties in this coastal strip cannot match.”
“The detail that caught our attention is the Officine Gullo kitchen: a professional Italian culinary brand whose equipment is found in Michelin-starred restaurants, installed here for guests to use daily alongside four ovens, a Thermomix and a Gaggenau refrigerator suite. Most villas at this price point in Chianti offer a well-appointed kitchen; very few offer one with genuine professional provenance. The combination of an active wine and olive oil estate with complimentary in-house wine tasting is also unusually integrated: unlike most Tuscan villas that simply sit near vineyards, Fieravista sits within one, and the cellar below is stocked with the estate's own production. For a group that genuinely cooks and eats well, this is one of the most purposefully equipped six-bedroom villas in the Chianti Classico zone.”
Why Tuscany
What makes Tuscany worth choosing
Vineyard estates in Chianti
Castellina in Chianti and Radda in Chianti hold some of the region's grandest wine estates, many still producing their own label alongside olive oil. Staying among the vines gives direct access to tastings most visitors only see from a tour bus.
Coast and countryside together
Forte dei Marmi adds a stretch of genuine Tuscan coastline, with beach clubs and marble mountain views a short drive from Lucca and Pisa. Groups who want both sea and hills often split a trip between the two.
Estates built for long stays
Properties around San Quirico d'Orcia and Barberino Tavarnelle sit on working farmland, often with a pool, tennis court and enough bedrooms to host multiple families for a week or longer. Rignano sull'Arno offers a similar setting closer to Florence.
Best time to visit
Local guide
Local guide to Tuscany
dining
Osteria di Trequanda
A respected, long-standing trattoria in the village of Trequanda serving Sienese classics with local Crete Senesi ingredients. Book ahead at weekends; it fills quickly with Italians from Siena and Arezzo.
Lorenzo
Forte dei Marmi's only Michelin-starred restaurant serves refined coastal cuisine with impeccable service in an elegant setting just minutes from the villa.
Ristorante Centanni
A family-run local favourite serving superb pici all'aglione and delicious peposa, representing authentic Tuscan cooking without tourist markup.
experience
Saturnia thermal baths
The natural thermal pools at Saturnia provide a uniquely restorative experience, with mineral-rich waters flowing at a constant 37°C throughout the year.
Leaning Tower of Pisa
The iconic 14th-century tower sits just ten minutes from the estate. Climb to the top for breathtaking views and time your visit for early morning to avoid crowds.
Brunello wine tasting in Montalcino
Montalcino is 22km from the villa and produces Brunello di Montalcino, one of Italy's most celebrated red wines. Several estates offer private cellar tastings by appointment, including Biondi-Santi, whose archive vintages date back to the 19th century.
activities
Argentario peninsula exploration
The Monte Argentario peninsula offers dramatic coastal scenery and sophisticated resort towns like Porto Ercole, combining natural beauty with elegant dining options.
Chianti Classico harvest season
The grape harvest runs across the Chianti Classico estates throughout September and into October. Several estates in the Radda and Gaiole communes welcome visitors for harvest participation and pressing days: your concierge can arrange access.
Truffle hunting in the San Miniato hills
Autumn brings white truffle season to Tuscany, and the San Miniato area west of Florence is one of the region's most productive zones. The concierge can arrange a guided hunt with a local trifolao, typically followed by a lunch using the morning's finds.
wellness
Bagno Vignoni thermal baths
The historic thermal spring at Bagno Vignoni sits in a Renaissance piazza rather than a conventional town square, and the surrounding area has several thermal pools open to the public and to hotel day guests. An easy half-day from the villa at 23km.
shopping
Via Spinetti
Forte dei Marmi's designer shopping street features flagship boutiques from Italy's finest fashion houses alongside exclusive resort wear collections.
Common Questions
Frequently Asked Questions about Tuscany
When is the best time to visit Tuscany for a luxury villa holiday?
May, June and September deliver warm days without the peak heat and crowds of July and August. Autumn in the Chianti countryside also brings the grape harvest, a popular time for wine-focused stays.
What types of luxury properties are available in Tuscany?
The collection spans vineyard estates in Chianti, converted farmhouses near San Quirico d'Orcia, and coastal villas around Forte dei Marmi. Most combine period architecture with modern interiors and a private pool.
How much does a luxury villa in Tuscany cost per week?
Weekly rates run from £4,000 to £229,000, with the widest range of any region in the collection. Grand estates near Florence and Chianti's wine country sit at the top, while smaller countryside villas offer a more moderate entry point.
What amenities do luxury properties in Tuscany typically include?
Private pools, outdoor dining terraces and vineyard or olive grove views are close to standard. Larger estates near Barberino Tavarnelle often add a tennis court, wine cellar and staff such as a housekeeper or chef.
How many guests can luxury villas in Tuscany accommodate?
Smaller farmhouses sleep four to eight guests, while the larger Chianti estates and properties near the Province of Grosseto can accommodate groups of twenty or more across several buildings. Coastal villas near Forte dei Marmi tend to suit mid-sized groups.
How do you get to Tuscany?
Florence and Pisa airports are the main gateways, both within roughly an hour of Chianti and the surrounding countryside. Forte dei Marmi and the coast are best reached via Pisa, with transfers of around forty minutes.
Which areas of Tuscany are best for a luxury villa stay?
Castellina in Chianti and Radda in Chianti suit wine-focused stays among the vines, Forte dei Marmi offers the best coastal base, and San Quirico d'Orcia and the Province of Grosseto give the quietest, most rural setting.
Is Tuscany suitable for families, couples or groups?
Yes. Large estates near Rignano sull'Arno and Barberino Tavarnelle suit multi-generational family groups, couples often prefer a smaller farmhouse near Lucca, and wine-focused groups gravitate to the Chianti estates around Castellina and Radda.
How far in advance should you book a luxury villa in Tuscany?
The most sought after Chianti estates are typically booked six to nine months ahead for summer weeks. Coastal villas near Forte dei Marmi follow a similar timeline, while countryside properties often have more flexibility closer to travel dates.
Our Selection in Tuscany
Our collection here is built around estates and farmhouses that reward a full week rather than a quick stopover. We look for genuine vineyard or olive grove settings, a well-kept pool and staff who understand both the land and the local wine. Prices vary enormously by property and season, so we weigh grandeur against practicality before adding anything new. Each estate is visited and checked before it earns a place in the collection.
The Chosen Stay