Vacation Rentals & Villas in Montepulciano

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3,635 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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$135

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$264

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$377

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$512

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$573

Wohnungen und Haueser auf sehr zentral gelegenem tosk. Bauernhof mit Pool

Castellina In Chianti condo

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 24

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Staffed property, Private pool

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$184

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$1,350

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$1,227

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$1,612

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$736

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$491

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$463

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: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$184

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: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$608

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Private pool, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$1,693

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Staffed property, Private pool

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Price per night from

$1,828

Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Private pool, Shared outdoor pool (unheated), Trampoline

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Price per night from

$74

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Private pool, Shared outdoor pool (unheated), Trampoline

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Price per night from

$123

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (unheated), Private pool, Staffed property, Trampoline

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Price per night from

$307

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

2 of 4 match: Shared outdoor pool (unheated), Private pool, Staffed property, Trampoline

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Price per night from

$307

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Shared outdoor pool (unheated), Private pool, Staffed property, Trampoline

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Price per night from

$86

La Cascina Hotel Appartments

Marsciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Staffed property, Private pool

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Price per night from

$87

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

2 of 4 match: Staffed property, Private pool, Shared outdoor pool (unheated), Trampoline

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Price per night from

$295

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Private pool, Shared outdoor pool (unheated), Trampoline

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Price per night from

$224

Fattoria Quercia al Poggio - Apartment Cappella 4

Barberino Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Trampoline, Private pool, Shared outdoor pool (unheated), Staffed property

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Price per night from

$99

Fattoria Quercia al Poggio - Apartment Cappella 2

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Trampoline, Private pool, Shared outdoor pool (unheated), Staffed property

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Price per night from

$182

"MARGHERITA", DOUBLE WITH TERRACE IN SAN GIMIGNANO

San Gimignano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Trampoline, Private pool, Shared outdoor pool (unheated), Staffed property

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Price per night from

$86

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Shared outdoor pool (unheated), Private pool, Staffed property, Trampoline

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Agriturismo Gello - Villa with panoramic pool in Tuscany - Chianciano Terme

Chianciano Terme villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$701

Wonderful private villa 12 people, swimming pool

San Terenziano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$600

SMALL DREAMS apartment SOLE near ASSISI and immersed in the green of Umbria

Valfabbrica villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$246

Farm Beautiful Braid

Cannara farmhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$417

Casale degli Olivi

San Giovanni del Pantano farmhouse

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$806

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$436

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Trampoline, Private pool

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Price per night from

$552

Viewing 38 of 3,635
rentals in Montepulciano

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