Val d'Orcia
Rolling hills south of Siena, with Pienza, Montalcino and Bagno Vignoni among the places to visit.
14 villas
Tuscany
Tuscany villas by area
Our villas cover 15 areas of Tuscany, from Chianti and the Val d’Orcia to Lucca and the Maremma, plus 3 private estates. Each area page lists its villas, the places worth a day out and practical advice. Not sure which area suits you? Our guide to where to stay in Tuscany compares them.
01Our largest collections
Three different kinds of Tuscany, with the most villas to choose from.
Chianti
Vineyards and villages between Florence and Siena. A useful base for wine tasting and days in either city.
9 villas
Lucca & Garfagnana
Stay near the walled city of Lucca or explore the mountain villages and walking routes of the Garfagnana.
7 villas
02More towns and areas
Smaller collections, and towns with villas close by.
Cortona
A hill town above the Val di Chiana, with countryside villas and access to eastern Tuscany and nearby Umbria.
1 villa
Maremma
Southern Tuscany’s coast and inland countryside, with beaches, nature reserves and small towns to explore.
1 villa1 article
Montalcino
Brunello wine country south of Siena, a walled hill town above vineyards and olive groves, with Sant'Antimo Abbey and the wide horizons of the Val d'Orcia below.
1 villa
Montepulciano
A hill town known for Vino Nobile, with vineyards and a convenient base for exploring the Val d’Orcia.
1 villa
Siena
Choose countryside accommodation around Siena for visits to the historic centre, Chianti and the Crete Senesi.
1 villa1 article
Arezzo
Historic towns, art and countryside in eastern Tuscany, with Arezzo as a starting point for exploring the area.
Villas nearby
Cetona
A small town in southern Tuscany, close to wooded hills and the thermal springs around San Casciano dei Bagni.
Villas nearby
Crete Senesi
Open clay hills and countryside south-east of Siena, suited to scenic drives and quieter villa stays.
Villas nearby
San Gimignano
Medieval towers, Vernaccia vineyards and countryside between Florence and Siena.
Villas nearby
Val d'Ambra
A valley of vineyards, olive groves and villages in the province of Arezzo, between Chianti and the Valdarno.
Villas nearby
Versilia
North-west Tuscany’s coast and hills, with beach clubs around Forte dei Marmi and art in Pietrasanta.
Villas nearby
Private estates
03Estates with several villas
One address, several houses: useful for larger groups and celebrations. Facilities, services and arrangements for booking several villas vary by estate.
Castiglion del Bosco
Estate villas near Montalcino in the Val d’Orcia, with vineyards and countryside around them.
13 villas
Castelfalfi
Villas on the Castelfalfi estate near Montaione, surrounded by vineyards and countryside. Services vary by villa.
5 villas1 article
Dimora Ghirlandaio
An estate in the hills of Impruneta near Florence, with several villas and shared estate facilities.
1 villa1 article
04Beyond Tuscany
Beyond Tuscany
Explore options outside Tuscany for a trip that includes other parts of Italy.
Villas nearby
Umbria
The neighbouring region east of Tuscany, with hill towns and countryside for a stay or a longer Italian itinerary.
Villas nearby
Still deciding?
Choose by the holiday you want
Our area guide compares each part of Tuscany for wine, beaches, walking, art cities and quiet. Or tell Smaranda your plans and she will suggest a shortlist.
New to Tuscany? The regions of Tuscany explained