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: Clothes dryer Staffed property Swing set or jungle gym

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Price per night from

$148

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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: Swing set or jungle gym, Clothes dryer, Staffed property

2 of 3 filters match

Price per night from

$1,033

Farmhouse Le Gualtiere

Sant'Albino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Clothes dryer, Staffed property, Swing set or jungle gym

1 of 3 filters match

Price per night from

$97

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Clothes dryer, 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 3 match: Clothes dryer, Staffed property, Swing set or jungle gym

1 of 3 filters match

Price per night from

$74

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 3 match: Clothes dryer, Swing set or jungle gym, Staffed property

1 of 3 filters match

Price per night from

$81

Villa Poggio Fagianino

Sant'Albino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Clothes dryer, Swing set or jungle gym, Staffed property

1 of 3 filters match

Price per night from

$358

Holiday Apartment in the historical palace.Marina

Montepulciano apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 3 match: Clothes dryer, Swing set or jungle gym, Staffed property

1 of 3 filters match

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 3 match: Clothes dryer, Swing set or jungle gym, Staffed property

1 of 3 filters match

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 3 match: Clothes dryer, Swing set or jungle gym, Staffed property

1 of 3 filters match

Price per night from

$194

Gues tHouse del Corso

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$161

Casa della Luna

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$99

Charming 1-Bed Apartment in Montepulciano

Bivio di San Biagio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$199

Colombi Palace Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$145

Montorio

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

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B&B in Montepulciano

Bivio di San Biagio apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$130

Il Tosco: your home in tuscany

Montepulciano guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$1,480

Casanova of the Woods

Montepulciano farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$506

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$555

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$144

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$1,110

il Molinaccio Montepulciano 3

Montepulciano farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$555

1 of 3 match: Swing set or jungle gym, Staffed property, Clothes dryer

1 of 3 filters match

Price per night from

$1,110

Great rentals within 20 miles that match your search

Walnut della Fonte

Radicondoli house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$173

Agriturismo Podere Sertofano - apt J

Barberino Val d'Elsa farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$155

Agriturismo Sertofano - apt K

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$185

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: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

Match: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$1,702

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: Clothes dryer Staffed property Swing set or jungle gym

All filters match

Price per night from

$124

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