Vacation Rentals & Villas in Montepulciano

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2,147 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool Staffed property Trampoline Tennis in town

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$738

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agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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$308

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$136

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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$86

VILLA TALCIONA

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Tennis in town, Heated pool, Trampoline

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Price per night from

$191

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$379

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$576

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$514

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, Tennis in town, Heated pool, Trampoline

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Price per night from

$111

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!

3 of 4 match: Staffed property, Tennis in town, Heated pool, Trampoline

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Price per night from

$1,229

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Tennis in town, Heated pool, Trampoline

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Price per night from

$437

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$1,696

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$1,229

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$610

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$465

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$1,615

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Heated pool, Tennis in town, Staffed property, Trampoline

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Price per night from

$1,356

Apartment 3 Stiozzi Palace Ridolfi Certaldo Alto

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Tennis in town, Staffed property

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Price per night from

$97

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$1,106

"Olivo Junior". Charming apartment in Podere Pietreta, old farmhouse with pool

Radicofani apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$172

Villa del Lago - Homelike Villas

Castiglione del Lago villa

  • 19 bedrooms
  • 15 bathrooms
  • sleeps 45

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$1,212

Villa Bellavista - Homelike Villas

Montegonzi house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$413

Villa Alessandro - Homelike Villas

Citta della Pieve villa

  • 17 bedrooms
  • 9 bathrooms
  • sleeps 37

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$1,785

Villa la Corte-Villa with pool and tennis court in the Chianti countryside

San Donato in Poggio villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$1,270

Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$331

Villa Colombini - Superb villa with private garden and pool in Val d'Orcia

Trequanda villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$508

Castelluccio - Arezzo, Toscana - Castelluccio Dependance - Arezzo, Toscana

Poggio d'Acona apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$279

Farmhouse Pianelli

Pergine Valdarno house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$369

Villa Castelluccio - Arezzo, Toscana - Villa Castelluccio - Subbiano, Private Po

Poggio d'Acona villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$611

Castelluccio - Arezzo, Toscana - Castelluccio Quadri - Arezzo, Toscana

Poggio d'Acona apartment

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

2 of 4 match: Staffed property, Trampoline, Tennis in town, Heated pool

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Price per night from

$439

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$1,832

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$2,107

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$3,588

Villa Miralaghi 8-9 WI-FI, Biliardo, Camino, Piscina riscaldata, Jacuzzi, Bocce

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$1,106

Exclusive Villa in countryside 8pers., heatable pool, Umbria/Tuscany, historic

Citta della Pieve villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Tennis in town, Heated pool, Staffed property

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Price per night from

$615

Tipico bilocale in un Borgo Toscano

Cavriglia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Tennis in town, Staffed property

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Price per night from

$134

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Heated pool, Tennis in town, Trampoline

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Price per night from

$123

Viewing 38 of 2,147
rentals in Montepulciano

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