Vacation Rentals & Villas in Montepulciano

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2,155 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Shared outdoor pool (heated) Staffed property Trampoline Cycling trips

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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$136

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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$265

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, Cycling trips, Shared outdoor pool (heated), Trampoline

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Price per night from

$111

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$86

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Cycling trips, Shared outdoor pool (heated), Trampoline

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Price per night from

$437

Tenuta I Terzi d Ombrone

Poggi del Sasso villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Cycling trips, Shared outdoor pool (heated), Staffed property

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Price per night from

$3,233

Casa Titty Residence Terme Siena

Serre di Rapolano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Cycling trips, Shared outdoor pool (heated), Staffed property

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Price per night from

$99

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$575

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$378

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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$514

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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$74

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: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$185

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

Radicofani apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Cycling trips, Shared outdoor pool (heated), Staffed property

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Price per night from

$172

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Shared outdoor pool (heated), Cycling trips, 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: Shared outdoor pool (heated), Cycling trips, 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: Shared outdoor pool (heated), Cycling trips, 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: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$464

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Shared outdoor pool (heated), Cycling trips, 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: Shared outdoor pool (heated), Cycling trips, Staffed property, Trampoline

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Price per night from

$1,354

Farm Humile - Agriculture and Hospitality B & B

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$222

Casa Vacanze San Pierino - Capanna

Monteroni d'Arbia hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$345

Casa Vacanze San Pierino - Il Pozzo

Monteroni d'Arbia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$197

Villa Mulinello, secluded in the country, panorama over Montepulciano valley.

Montefollonico house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$283

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Casale dei Pianetti

Sovana farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Price per night from

$185

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Price per night from

$615

Camera n2 Gelso

Barberino Tavarnellle private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$93

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Price per night from

$123

Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Borgo di Mezzo

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$111

Agriturismo Poggio dell'Artista Chagalle

Vaiano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$172

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

2 of 4 filters match

Price per night from

$222

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$222

The VILLA of your dreams: FAMILY GROUPS, KIDS, FRIENDS and PETS - Siena: 12min

Monteriggioni villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 20

Responds fast! avg. 15 minutes

2 of 4 match: Staffed property, Shared outdoor pool (heated), Cycling trips, Trampoline

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Price per night from

$517

Apartment in farmhouse in San Gimignano

San Gimignano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 4 match: Shared outdoor pool (heated), Trampoline, Cycling trips, Staffed property

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Price per night from

$222

Viewing 38 of 2,155
rentals in Montepulciano

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