Vacation Rentals & Villas in Montepulciano

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Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$148

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Farmhouse Le Gualtiere

Sant'Albino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Staffed property, Swing set or jungle gym

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Price per night from

$97

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$198

Tuscany Villa in Argiano near Montepulciano B&B 1 Room, swimming pool, wifi

Montepulciano b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Staffed property, Swing set or jungle gym

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Price per night from

$74

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$81

Villa Poggio Fagianino

Sant'Albino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$358

Holiday Apartment in the historical palace.Marina

Montepulciano apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$173

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

Bivio di San Biagio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$309

I Tigli, apt in farmhouse only 5 km to Montepulciano. 2 bedrooms, pool and Wi-Fi

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Staffed property

1 of 2 filters match

Price per night from

$194

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

1 of 2 match: Swing set or jungle gym, Staffed property

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Price per night from

$1,033

Great rentals within 20 miles that match your search

Agriturismo Torre di Sant' Ansano

Ville di Corsano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swing set or jungle gym

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Price per night from

$99

Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swing set or jungle gym

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Price per night from

$266

Casale at Petriolo-private pool

Casal di Pari villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 21 minutes

Match: Staffed property Swing set or jungle gym

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Price per night from

$247

Private Villa with a wonderful view and private pool, close to Siena

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Staffed property Swing set or jungle gym

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Price per night from

$445

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Staffed property Swing set or jungle gym

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Price per night from

$432

Tuscany country apartment for 4

Buonconvento apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$247

Accommodation in chianti

Vagliagli apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Staffed property Swing set or jungle gym

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Price per night from

$74

Agriturismo Il Drago App. La Tinaia

Bucine finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Staffed property Swing set or jungle gym

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Price per night from

$130

Vernianello Type A

Cedda farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$185

Le Stalle, Podere Patrignone

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Staffed property Swing set or jungle gym

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Price per night from

$266

Walnut della Fonte

Radicondoli house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$173

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Staffed property Swing set or jungle gym

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Price per night from

$136

Agriturismo Incrociata Greppia

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$195

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$121

Agriturismo Il Drago App. La Stalla

Bucine townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$186

Agriturismo "Casa al Gianni" - Fico

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Staffed property Swing set or jungle gym

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Price per night from

$161

Agriturismo Incrociata Granaio

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Staffed property Swing set or jungle gym

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Price per night from

$136

Agriturismo Incrociata Dispensa

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Staffed property Swing set or jungle gym

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Price per night from

$136

Pulcianese in the countryside of the Tuscan hills but a stone's throw from Siena

Ville di Corsano farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swing set or jungle gym

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Price per night from

$124

Villa Patrignone 7 bedroom Tuscany villa with pool

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Staffed property Swing set or jungle gym

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Price per night from

$612

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

Match: Staffed property Swing set or jungle gym

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Price per night from

$1,703

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!

Match: Staffed property Swing set or jungle gym

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Price per night from

$611

Agriturismo "Casa al Gianni" - Capanna

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Staffed property Swing set or jungle gym

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Price per night from

$136

Agriturismo Il Drago App. The Barn

Bucine finca

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Staffed property Swing set or jungle gym

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Price per night from

$185

Agriturismo "Casa al Gianni" - Olmo

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$148

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Staffed property Swing set or jungle gym

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Price per night from

$1,234

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Staffed property Swing set or jungle gym

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Price per night from

$1,234

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Swing set or jungle gym

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Price per night from

$1,234

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