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Luxury Villas in the Siena Area

Rich red wines and stirringly beautiful Tuscan landscapes await those who pick luxury villa rentals in the Siena area.

Luxury Villas in the Siena Area

The Siena area is the heart of Tuscany and a picture of quintessential Italian countryside. The great masterpiece that is the Gothic city of Siena crowns a bluff in the middle as swathes of softly contoured vineyards and farms roll onto the horizon. Slender Mediterranean cypress trees dance in the balmy breezes. Ancient farmhouses punctuate the ridges. Hill towns – tinted gold and terracotta red – cap the summits. Prepare to be enchanted.

Most will focus their attention on the north. That’s where the prestigious wine country of the Chianti Valley opens in all its glory. Sumptuous vineyards and cellar doors beckon travelling epicureans there with the promise of award-winning tipples made from Sangiovese grapes, highly smoked and heavy, with overtones of dark cherry and oregano. But Chianti is also the land of hill towns, like magical Montefioralle and walled Monteriggioni, ideal for day trips from your luxury villa.

The southern side of Siena is wilder; the Tuscan backcountry fragments into badlands and sun-baked ridges and is known as the Crete Senese for its barren appearance. However, there are places of refuge, including the stunning hilltop town of Montepulciano, home of the fine-aged vino nobile and a stunning piazza capped by the Torre di Pulcinella. Another is Pienza, a town famed as the first example of real urban planning, where elegant Papal palazzos and mediaeval arcades flank the streets.

The Val d’Orcia – UNESCO-tagged and legendary – also deserves a special mention for guests looking to holiday in a luxury villa in the Siena area. It’s a disarmingly beautiful part of the country, where the light dances ethereally on the hills, and the landscapes are a colour palette of beiges, browns, tans, and emerald greens. Within, you’ll unravel tales of great Italian banditos at Radicofani, sample some of the world’s best wines at Montalcino, and bathe in wild hot springs between the woods of Bagni di San Filippo.

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See

  • The stunning, UNESCO-protected Val d'Orcia region
  • Landscapes of rolling hills and verdant vineyards
  • The impressive tower of Radicofani Castle

Experience

  • Taste the fine wines of Chianti
  • Bathe in the hot springs of Bagni di San Filippo
  • Explore enthralling towns like Montepulciano and Monteriggioni
26 Properties found Sort by

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Podere Tesoro

Siena Area, Tuscany, Italy, Europe

Bedrooms: 10, Guests: 22
From 30,000 to 68,040 EUR per week

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Villa Cetinale

Siena Area, Tuscany, Italy, Europe

Bedrooms: 13, Guests: 25
From 25,000 to 60,000 EUR per week

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Villa Il Cellese

Siena Area, Tuscany, Italy, Europe

Bedrooms: 10, Guests: 19
From 56,000 to 56,000 EUR per week

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Villa Castelnuovo Tancredi

Siena Area, Tuscany, Italy, Europe

Bedrooms: 8, Guests: 16
From 28,000 to 33,000 EUR per week

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Villa San Gerolamo

Siena Area, Tuscany, Italy, Europe

Bedrooms: 5, Guests: 10
From 13,500 to 27,000 EUR per week

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Villa Podere Capannelle

Siena Area, Tuscany, Italy, Europe

Bedrooms: 7, Guests: 14
From 22,500 to 25,000 EUR per week

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Villa Principe

Siena Area, Tuscany, Italy, Europe

Bedrooms: 6, Guests: 12
From 15,000 to 25,000 EUR per week

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Villa Monte Mario

Siena Area, Tuscany, Italy, Europe

Bedrooms: 7, Guests: 14
From 16,250 to 21,250 EUR per week

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Villa Mugnello

Siena Area, Tuscany, Italy, Europe

Bedrooms: 10, Guests: 20
From 14,000 to 21,000 EUR per week

Aerial view of country estate with two brick villas behind a swimming pool

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Tenuta La Ripa

Siena Area, Tuscany, Italy, Europe

Bedrooms: 6, Guests: 12
From 13,000 to 15,000 EUR per week

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Villa Montesoli

Siena Area, Tuscany, Italy, Europe

Bedrooms: 9, Guests: 18
From 11,000 to 15,000 EUR per week

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Villa Poggio Fibbia

Siena Area, Tuscany, Italy, Europe

Bedrooms: 5, Guests: 10
From 10,500 to 12,600 EUR per week

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Villa Alba

Siena Area, Tuscany, Italy, Europe

Bedrooms: 3, Guests: 6
From 27,335 EUR per week, to price on request

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Villa Benefizio

Siena Area, Tuscany, Italy, Europe

Bedrooms: 6, Guests: 12
From 16,464 EUR per week, to price on request

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Villa Biondi

Siena Area, Tuscany, Italy, Europe

Bedrooms: 5, Guests: 10
From 44,275 EUR per week, to price on request

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Villa Case Crete

Siena Area, Tuscany, Italy, Europe

Bedrooms: 9, Guests: 18
From 10,824 EUR per week, to price on request

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Villa Castello

Siena Area, Tuscany, Italy, Europe

Bedrooms: 3, Guests: 6
From 27,335 EUR per week, to price on request

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Villa Chiusa

Siena Area, Tuscany, Italy, Europe

Bedrooms: 4, Guests: 8
From 37,730 EUR per week, to price on request

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Villa Conti

Siena Area, Tuscany, Italy, Europe

Bedrooms: 7, Guests: 14
From 10,070 EUR per week, to price on request

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Villa del Fiume

Siena Area, Tuscany, Italy, Europe

Bedrooms: 4, Guests: 8
From 37,730 EUR per week, to price on request

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Villa Gauggiole

Siena Area, Tuscany, Italy, Europe

Bedrooms: 4, Guests: 8
From 37,730 EUR per week, to price on request

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Villa La Foce

Siena Area, Tuscany, Italy, Europe

Bedrooms: 12, Guests: 24
From 40,000 EUR per week, to price on request

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Villa Oddi

Siena Area, Tuscany, Italy, Europe

Bedrooms: 6, Guests: 12
From 50,820 EUR per week, to price on request

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Villa Oliviera

Siena Area, Tuscany, Italy, Europe

Bedrooms: 3, Guests: 6
From 27,335 EUR per week, to price on request

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Villa Sant'Anna

Siena Area, Tuscany, Italy, Europe

Bedrooms: 5, Guests: 9
From 42,931 EUR per week, to price on request

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Villa Stabbi

Siena Area, Tuscany, Italy, Europe

Bedrooms: 5, Guests: 9
From 42,931 EUR per week, to price on request

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