A curated selection of luxury holiday villas in Siena & Montepulciano, Italy
Rent a luxury villa in Siena or Montepulciano, Tuscany, to immerse yourself in a land where each day is lived to the fullest, where the simplest of ingredients become the most incredible food experience, and where 'la dolce vita' is a way of life. View our portfolio of luxury holiday villas in Siena & Montepulciano for 2026.
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Sovicille, Tuscany
Ref. CH1009
14 Guests - 7 Bedrooms - 7 Bathrooms
8 610€ - 16 940€/week
San Gimignano, Tuscany
Ref. CH1003
14 Guests - 7 Bedrooms - 8 Bathrooms
12 075€ - 17 500€/week
Buonconvento, Tuscany
Ref. MP1002
9 Guests - 4 Bedrooms - 4 Bathrooms
3 080€ - 10 010€/week
Monteroni d'Arbia, Tuscany
Ref. SN1006
16 Guests - 6 Bedrooms - 9 Bathrooms
24 710€ - 36 750€/week
Buonconvento, Tuscany
Ref. SN1001
14 Guests - 7 Bedrooms - 8 Bathrooms
31 220€ - 41 265€/week
Montepulciano, Tuscany
Ref. TU1004
12 Guests - 6 Bedrooms - 5 Bathrooms
10 360€ - 14 945€/week
Get in touch with us
Connect with us and let one of our reservation agents understand your criteria and help match you to the home that best suits your occasion. We work with a number of privately listed properties that may be just what you're looking for.
Get to know Siena & Montepulciano
Explore our portfolio of luxury villa rentals in Tuscany, which offers a large selection for you to choose from to experience the Italian countryside with your friends and family in 2026. Our Tuscan villas have incredible amenities including private pools, picturesque hillside views, outdoor dining areas for al fresco meals and beautiful Italian gardens.
Whether you’re looking for a historic holiday villa among olive groves and vineyards or a traditional Tuscan farmhouse that is elegant in design, we can help you find the perfect vacation rental for your stay. If you are travelling with young children, we can advise you on the best child-friendly villas. Our family villas are situated in and around Lucca, Florence, Siena and the Chianti Region as well as the Tuscan coast including the famous seaside resort, Forte dei Marmi. In addition, you can explore our portfolio of private villas in Tuscany for large groups.
Regarded as the birthplace of the Italian Renaissance, Tuscany is home to the world’s most recognizable Renaissance art and architecture including Michelangelo’s statue of David, Botticelli’s works in the Uffizi Gallery and the Duomo basilica. Tuscany’s diverse landscape includes the picturesque olive groves and vineyards of Chianti, the rugged Apennine Mountains and a beautiful coast including the glitzy resort towns of Forte Dei Marmi and Viareggio. Explore Florence, even if only for a day, and visit its museums, shops and restaurants, walk the winding cobblestone streets of Siena or enjoy a day wandering the beautiful town of Lucca. Travel to discover hidden gems such as Volterra or Pienza and get lost in Tuscan towns that are lesser known but well worth visiting. Rooted in Italian history, this exceptional region that is dotted with cypress trees and vines and complemented with incredible local cuisine, is the quintessential holiday destination for refined relaxation.
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© 2026 A.M.A Selections. All rights reserved
© 2026 A.M.A Selections. All rights reserved