Vacation Rentals & Villas in Montepulciano

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1,090 Houses

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

Match: Ceiling Fans Staffed property Trampoline Car not required

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Price per night from

$1,616

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appartamento grazia centro storico

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Car not required

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Price per night from

$185

Casa San Gimi Perfect Location

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Car not required

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Price per night from

$104

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$308

WINERY HOTEL in the Chianti Classico area "Apt PILU" ADULT ONLY +14

Greve in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 10 minutes

3 of 4 match: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$308

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: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$185

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,697

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,230

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$738

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: Car not required, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$610

La Cascina Hotel Appartments

Marsciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Car not required

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Price per night from

$88

Casa Malichi - Rètro Apartment - Centro storico Perugia

Perugia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$160

Casatorre le volte city centre

Perugia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 49 minutes

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$160

Casa Mila Garden Apartment

Sansepolcro apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$93

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Car not required, Staffed property, Trampoline

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Price per night from

$86

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Ceiling Fans, Car not required, Staffed property, Trampoline

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Price per night from

$136

Enjoy Siena and its country!A medieval experience

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$197

Stay in a medieval tower in Siena! Apt for two.

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$123

Appartamento signorile con soffitto a volte nel centro di Assisi

Assisi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$136

Casa Falcucci

Gubbio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$110

Red House Gubbio

Gubbio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$173

Ride the Beauty appartamento verde con la terrazza al centro di Assisi

Assisi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$160

Casa Mila Top Floor apartment ID 422451, Sansepolcro, Province of Arezzo, Italy

Sansepolcro apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$93

House "The three Muses"

Deruta b&b

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$62

Ele Home

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Trampoline, Staffed property, Ceiling Fans, Car not required

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Price per night from

$93

GH Paradiso - Apartment - Split Level (C)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$185

GH Paradiso - Large 2 Bedrooms Apartment (B)

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$185

GH Paradiso - 2 Bedrooms Apartment (A)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$185

a casa di Arianna e Isabella

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$209

Few Steps from the Duomo - Luxury Penthouse

Siena hotel apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 16

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$240

Few Steps from the Duomo - Luxury Apartment

Siena hotel apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$141

Few Steps from the Duomo - Luxury Apartment 2

Siena hotel apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$141

Holiday Apartment in the historical palace.Marina

Montepulciano apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$173

Romantic Suite

Gubbio townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$173

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 4 match: Trampoline, Car not required, Ceiling Fans, Staffed property

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Price per night from

$99

2 MINI APPARTAMENTI ELEGANTI INDIPENDENTI CON PARCHEGGIO

San Martino in Colle house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Trampoline, Car not required, Ceiling Fans, Staffed property

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Price per night from

$80

Fidanza House a few steps from Civita di Bagnoregio

Bagnoregio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$148

Big Apartment with Garden

Siena apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Car not required

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Price per night from

$479

Viewing 38 of 1,090
rentals in Montepulciano

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