Vacation Rentals & Villas in Montepulciano

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311 Houses

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$3,158

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

Match: Safe Solarium or roof terrace Staffed property

All filters match

Price per night from

$3,519

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$2,788

Casa Titty Residence Terme Siena

Serre di Rapolano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$99

Girasole - suite # number 2

Cortona villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$177

La Corte, one bedroom apt on the ground floor close Asciano. Pool, A/C & Wi-Fi

Rapolano Terme apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$149

Villa Portoverde

Foiano Della Chiana villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Safe Solarium or roof terrace Staffed property

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Price per night from

$578

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La Spiga D'oro -Granaio

Foiano Della Chiana apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$124

B & B THE OLD Lieutenancy SUITE TRIPLE

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 13 minutes

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$99

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$198

Villa Poggio Fagianino

Sant'Albino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$358

podere la giuda

Sinalunga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

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Tuscany Villa in Montepulciano,Free Parking,Free Wi-fi,view of valley

Bivio di San Biagio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$309

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$222

Farm Humile - Agriculture and Hospitality B & B

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$222

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$222

Fungus

Lucignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Staffed property, Safe, Solarium or roof terrace

2 of 3 filters match

Price per night from

$147

Podere Monti

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

2 of 3 match: Staffed property, Safe, Solarium or roof terrace

2 of 3 filters match

Price per night from

$1,358

il Giardino di s. Agostino

Cortona house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Staffed property, Safe, Solarium or roof terrace

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The Flowered Farmhouse in Cortona, Apartment Rosa

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$235

The Flowered Farmhouse Cortona, Apartment Margherita

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$247

The Flowered Farmhouse in Cortona Apartment Glicine

Cortona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$223

The Flowered Farmhouse in Cortona, Apartment Lavanda

Cortona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$272

The Flowered Farmhouse in Cortona, Apartment Tulipano

Centoia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$272

Agriturismo Il Torrino

Cortona villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$511

Wonderful and romantic Tuscany

Foiano Della Chiana villa

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 30

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$864

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$617

Il Pozzo, beautiful apartment in the Crete Senesi area. Hot tub, pool, A/C, WiFi

Rapolano Terme apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$149

Villa Montichiello

Monticchiello villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$570

Le Palazze, country b&b

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 30 minutes

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$186

B & B THE OLD Lieutenancy APARTMENT LA ROCCA

Citta della Pieve b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 13 minutes

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$223

2 of 3 match: Solarium or roof terrace, Safe, Staffed property

2 of 3 filters match

Price per night from

$926

Holiday Villa in Cortona, La Fiorita

Cortona farmhouse

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 20

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$1,411

COUNTRY HOUSE CETONA

Cetona farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$260

Fonte Cicerum stone villa with eco infinity pool - a Fontanaro Property

Paciano house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$988

VILLA FLAMINIO total privacy in the villa for exclusive use

Tuoro sul Trasimeno farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$265

Tuscany villa, private pool, for family & group

Mercatale di Cortona farmhouse

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 24

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

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Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

2 of 3 match: Safe, Solarium or roof terrace, Staffed property

2 of 3 filters match

Price per night from

$1,033

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rentals in Montepulciano

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