Vacation Rentals & Villas in Pienza

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Price per night from

$907

luxury villa few steps from Pienza, outdoor-indoor swimming pool,air-conditoned

Pienza apartment

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 58 minutes

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$1,580

Source Val'd'Orcia Sienese farmhouse with pool and air conditioning

Monticchiello apartment

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 12

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$835

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Price per night from

$1,755

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$907

The quiet rooms in Pienza

Pienza b&b

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Villa with Pool in Monticchiello,Aircon,Garden,Barbecue,Table Tennis,sleeps 14

Monticchiello villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$606

Villa Montichiello

Monticchiello villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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$569

Great rentals within 20 miles that match your search

Tuscan private villa with large pool and garden

Chiusi villa

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$666

IL CASALE TOSCANO

Cortona house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 10

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$614

Agriturismo il Poggio di Cantagallina

Castiglione del Lago apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$111

Casa vacanze panoramicissima,zona tranquilla

Sarteano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$117

Beautiful family home Lake Trasimeno / Tuscany border

Petrignano house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$307

ANTICO PALLAIO

Cortona villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$492

Madonna Delle Grazie - double bedroom

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Charminghills villas in Umbria

Citta della Pieve farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

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$921

Sassicaia the wine lover home - a Fontanaro Property

Paciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$356

Frantoio the 19th Century home - a Fontanaro Property

Lake Trasimeno farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$307

COUNTRY HOUSE CETONA

Cetona farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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$258

Borgo La Bagnaia #Villa Sarageto

San Giovanni d'Asso villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 43 minutes

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$860

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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Price per night from

$1,228

Tuscany country apartment for 4

Buonconvento apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$246

Desiderio, the wine lover home with pool - a Fontanaro Property

Paciano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$356

Poste del Chiugi

Petrignano del Lago apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$492

Agriturismo Villa Panorama - 8 posti letto - Villa esclusiva - Siena

Rigaiolo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$590

Macciangrosso

Chiusi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$197

Orcia Valley country house, swimmimg pool, children play ground, table tennis

Castiglione D'Orcia villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 17

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$569

Tignanello: Tuscan Style home for wine lovers - a Fontanaro Property

Paciano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$356

Madonna delle Grazie-matrimonile room

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$111

Holiday Villa in Cortona, La Fiorita

Cortona farmhouse

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$1,404

Borgo Castelrotto, pool villa 18 guests at Castelnuovo Tancredi Estate

Buonconvento farmhouse

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$1,720

la lodola

Crete Senesi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

Scannelli Farm

Val d'Orcia b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$148

The Flowered Farmhouse in Cortona, Apartment Rosa

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$234

The Flowered Farmhouse in Cortona Apartment Glicine

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$221

The Flowered Farmhouse Cortona, Apartment Margherita

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$246

the grinders with large porch and large garden

Monte San Savino b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 32 minutes

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Price per night from

$117

The Flowered Farmhouse in Cortona, Apartment Lavanda

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$271

Viewing 38 of 129
rentals in Pienza

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