Curated Luxury Properties · Tuscany · 10 Stays
Luxury Villas in Tuscany, Italy
Tuscany draws luxury travellers with a landscape that shifts from the Tyrrhenian coastline at Forte dei Marmi to the rolling hills around Rignano sull'Arno, each area carrying its own distinct character and centuries of cultural weight. The region's private estates and restored villas sit among vineyards, olive groves and medieval hilltop villages, making it one of Italy's most compelling destinations for an extended stay. From the Maremma wilderness in the Province of Grosseto to the architectural grandeur near Pisa, the variety here is remarkable.
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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
Landscapes that shift dramatically
The Tuscan terrain covers far more ground than the classic cypress-lined postcard. South of Siena, the clay ridges of the Crete Senesi create an almost lunar panorama, while the Maremma coast in the Province of Grosseto delivers rugged, unspoilt shoreline. Forte dei Marmi, by contrast, brings a refined beach-club culture backed by the Apuan Alps.
A living culinary tradition
Tuscany's food culture operates at every level, from Michelin-starred restaurants in Cortona and Florence to neighbourhood trattorias serving ribollita and bistecca alla fiorentina. Many villas include private chefs who source directly from local markets in Greve in Chianti or San Gimignano. The region also produces some of the world's most sought-after wines, with Brunello di Montalcino and Bolgheri Super Tuscans available at cellar-door tastings.
Architecture with genuine provenance
Luxury properties here tend to be restored farmhouses, Renaissance-era villas or converted country estates rather than new-build resorts. Stone walls, terracotta floors, loggias and frescoed ceilings are common, lending each property a tangible connection to the region's past. Around Rignano sull'Arno, estates often sit within working agricultural land, adding an authenticity that purpose-built accommodation cannot replicate.
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?
Peak season runs from mid-June through August, bringing warm temperatures, long evenings and the liveliest atmosphere along the coast. May, early June, September and October are shoulder months that deliver excellent weather, lower rates and quieter roads, making them ideal for vineyard visits and cultural touring. Spring also coincides with wildflower season across the Val d'Orcia, while autumn brings the olive and grape harvests.
What types of luxury properties are available in Tuscany?
TheChosenStay curates a hand-picked collection of private villas and estates across Tuscany, ranging from restored Renaissance country houses to contemporary coastal retreats. Many retain original architectural features such as stone arches, beamed ceilings and chapel conversions, while incorporating modern comforts. Larger estates often include multiple buildings set within private grounds, making them well suited to multi-generational gatherings or group celebrations.
How much does a luxury villa in Tuscany cost per week?
Weekly rates in our collection range from approximately €1,500 for a smaller villa in the shoulder season to €260,000 for the most exclusive estates at peak summer. Prices typically rise sharply in July and August, particularly for coastal properties near Forte dei Marmi. Booking during May, June or September can reduce costs significantly while still guaranteeing warm weather and full availability of local restaurants and attractions.
What amenities do luxury properties in Tuscany typically include?
Private swimming pools are standard across nearly all properties, often set within landscaped gardens with views over vineyards or hills. Many villas provide dedicated staff including housekeepers, gardeners and private chefs who prepare meals using local ingredients. Larger estates may also feature tennis courts, wine cellars, outdoor dining terraces, heated pools and spa facilities.
How many guests can luxury villas in Tuscany accommodate?
Smaller villas suit couples or families of four to six, while mid-range properties comfortably sleep eight to twelve guests across multiple bedrooms. The largest estates in our collection can host groups of twenty or more, with separate annexes and guest houses providing privacy within a shared setting.
How do you get to Tuscany?
Florence Airport (Peretola) and Pisa International Airport serve the region directly, with Pisa receiving a wider range of European flights. Rome Fiumicino sits roughly two and a half hours south by car, making it a practical option for long-haul arrivals. Private transfers, helicopter charters and car hire are all readily available, and most properties in the Chianti or Val d'Orcia areas sit within sixty to ninety minutes of either Tuscan airport.
Which areas of Tuscany are best for a luxury villa stay?
Forte dei Marmi is the region's most glamorous coastal address, known for its designer boutiques and beach clubs. The Province of Grosseto covers the wilder Maremma coast and its hinterland, appealing to those who prefer seclusion and natural beauty. Rignano sull'Arno places guests within easy reach of Florence, while the Chianti hills, Val d'Orcia and Lucca each bring their own distinct blend of culture, landscape and gastronomy.
Is Tuscany suitable for families, couples or groups?
Tuscany works exceptionally well for all three. Families benefit from properties with large grounds, pools and proximity to beaches or hill towns with gelaterias and piazzas to explore. Couples gravitate towards smaller villas in the Chianti or Montalcino wine regions, while large groups and wedding parties find that multi-building estates provide communal space alongside private quarters.
How far in advance should you book a luxury villa in Tuscany?
For peak weeks in July and August, booking six to twelve months ahead is advisable, as the most desirable properties fill quickly. Shoulder season stays in May, June or September allow more flexibility, though three to six months' lead time still helps secure a first-choice property. TheChosenStay can assist with availability across our curated collection at any stage of planning.
Our Selection in Tuscany
Tuscany rewards the traveller who wants more than a hotel lobby. It suits those who prefer to live inside a landscape rather than simply look at it: cooking with ingredients from the morning market, swimming as the late sun catches the olive trees, reading on a terrace that has stood for three hundred years. Our collection here reflects a curation philosophy built on character, provenance and privacy. Every property we feature has been personally assessed, and each one earns its place through genuine quality rather than scale or flash. This is where slow travel finds its finest expression.
The Chosen Stay