Vacation Rentals & Villas in Montepulciano

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2,466 Houses

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Tuscany Chalet in family camping by the sea, near Pisa and Lucca

Viareggio caravan/mobile home

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Table tennis, Sea view, Trampoline

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$34

Convento San Francesco

Lugnano in Teverina apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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CINZIA'S HOUSE 2

Soiana b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

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$110

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$86

Apartment in Farmhouse near the sea with a bedroom

Riparbella apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 46 minutes

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$98

ELBA DISCOUNT SHIP direct access to the sea with private cove garden

Porto Azzurro townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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$110

Apartment in Farmhouse near the sea with two bedrooms

Riparbella apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 46 minutes

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$134

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$262

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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$87

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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Price per night from

$87

Borgo ai Lecci, Amazing Stone Villa in the heart of Tuscany

Orentano villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$784

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$73

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$109

La Villa - Luxury Home

Configni villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 12 minutes

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$670

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$131

Villa Giuliana, appartamento BILOCALE 4 Ptl, all'Isola d'Elba.

Capoliveri townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$67

Apartment in Farmhouse (Rosa 4+2) province of Pisa,Volterra area, San Gimignano

Volterra farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$109

Apartment in Farmhouse (Girasole 6+1) province of Pisa, Volterra, San Gimignano

Volterra farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$131

Apartment in Farmhouse (Viola 2+2) province of Pisa, Volterra, San Gimignano

Volterra farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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$87

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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$87

BUTTERFLY

Castiglioncello house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Table tennis, Sea view, Trampoline

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$113

Feel-good holiday in the midst of the olive grove

Sassofortino house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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$145

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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$1,600

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$731

guardalaluna villa holiday House

Pian di Sco b&b

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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$402

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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$183

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: Sea view, Table tennis, Staffed property, Trampoline

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Price per night from

$603

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,680

Marietto's House: Rustic Tuscan villa near historic Lucca

Cappella farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$268

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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Price per night from

$280

Chalet in Toscane aan zee te huur | Camping Paradiso in Viareggio | Italië

Viareggio chalet

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$80

Villa Brolio Quinto,exclusive use,secluded with large park and pool.

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

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$487

Spoleto Country House

Strettura villa

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 32

Responds fast! avg. 3 hours 10 minutes

3 of 4 match: Sea view, Table tennis, Staffed property, Trampoline

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Price per night from

$2,261

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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$1,341

Family villa Tuscany slps15 stunning sea/mountain views, beach/village 5 mins

Porto Ercole house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Staffed property, Table tennis, Sea view, Trampoline

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$509

Villa Liburnia B&B

Livorno apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Table tennis, Sea view, Staffed property

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$140

Villa Valle, incredible place at the seaside

Porto Santo Stefano apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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$731

Viewing 38 of 2,466
rentals in Montepulciano

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