Vacation Rentals & Villas in Montepulciano

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42 Houses

Villa LA VALIANA (Montepulciano)

Montepulciano villa

4 bedrooms / 5 bathrooms / sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

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Price per night from

$589

Great rentals within 20 miles that match your search

Villa Osservatorio

Monticiano villa

14 bedrooms / 14 bathrooms / sleeps 27

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Price per night from

$3,625

Villa with Pool and Jacuzzi private Deal 2020

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 42 minutes

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Price per night from

$121

Amazing villa with swimming-pool

Monteroni d'Arbia villa

9 bedrooms / 6 bathrooms / sleeps 19

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Price per night from

$1,399

Villa Castellare de Sernigi stunning sunsets

Tavarnelle Val di Pesa villa

6 bedrooms / 8 bathrooms / sleeps 14

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$1,308

Siena San Fabiano climatized villa with outdoor heated pool

Siena villa

9 bedrooms / 6 bathrooms / sleeps 18

“The Best Place to Celebrate your Birthday with Friends” Coming back to "San Fabiano" is like coming back to friends. If you wish to forget all your day-by-day problems, come to stay at this place. Located in the middle of the farm fields. Sit under the beautiful trees next to the pool and listen to the wind, and understand the value of the word tranquility. We were a party of three rooms, celebrating my round birthday. This is certainly not the last time they will see me at "San Fabiano".

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Price per night from

$903

Villa Parmolaia

Ville di Corsano villa

7 bedrooms / 7 bathrooms / sleeps 14

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Price per night from

$2,027

Amazing tuscan villa in front of Brunello's hills

Monticiano villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$271

Rapale Villa Sleeps 20 with Pool and WiFi - 5834722

Rapale villa

9 bedrooms / 9 bathrooms / sleeps 20

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$1,771

Villa La Coccola - Seductive villa for 8 persons with heated pool and A/C

Poggibonsi villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$387

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Price per night from

$1,414

VILLA TALCIONA

Poggibonsi apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$174

la lodola

Crete Senesi apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$155

Barn overlooking the vineyards

Gaiole in Chianti barn

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$142

Villa Colombaio

Asciano villa

5 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$644

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

5 bedrooms / 6 bathrooms / sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

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Price per night from

$1,604

Holiday Home Le Corniole

Civitella in Val di Chiana villa

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$92

Villa il Roseto

Gaiole in Chianti house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$589

Villa Pergine

Pergine Valdarno house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$433

Casale Stroncoli

Rapolano Terme villa

8 bedrooms / 8 bathrooms / sleeps 16

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Price per night from

$702

Villa Il Santo

Petrognano villa

8 bedrooms / 10 bathrooms / sleeps 16

“Perfect and Beautiful Experience” Our stay at the villa was such a wonderful experience. The view was breathtaking -- the villa beautiful, luxurious, comfortable, and clean We loved every minute of it. The owners annagloria and her husband, Enzo, were very helpful and gracious. The experience was truly beautiful -- it definitely exceeded our expectations. The location was ideal and allowed us to travel to many towns in beautiful Tuscany. Try the wines from the owners vineyard -- delicious. A cook hired by the Corti's prepared several excellent meals. A truly awesome experience. Everyone in our family loved our stay at this special villa.

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$1,748

Chianti house, Florence, Jacuzzi, Tuscany up to 6p

Montefienali house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 59 minutes

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Price per night from

$70

Villa Ripertoli luxury secluded family-owned farmhouse, Tuscany

Greve in Chianti villa

8 bedrooms / 9 bathrooms / sleeps 17

“Second visit as great as the first!” We have rented the Ripertoli property twice in the past three years. We spent a wonderful week there in 2010 and then two weeks in October of 2013. The location is exceptional, both for it's proximity to the heart of Chianti Classico, and for the sheer beauty of the area. Great cycling, hiking, and relaxing. As a professional caterer, I particularly enjoy the great availability of local foods and the well equipped kitchen that Deborah has put together. The home is large, plently of privacy as well as wonderful common area with a great kitchen and sitting area. The grounds are great as well. There are a plethora of great restaurants in the area, varying in price and style. Greve has plenty of local grocers including a wonderful local butcher shop run by Paulo and his mother, and a great green grocer as well as two bakeries, excellent gelato, and all of the other typical but essential shops.

Responds fast! avg. 2 hours 33 minutes

Match: Private outdoor pool (heated)

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Price per night from

$584

Farm in Chianti

Castelnuovo Berardenga villa

6 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$565

villa with a view of the valley

Chiusdino villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 9 minutes

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Price per night from

$123

Villa Capannole Tontenano Chianti private pool 12 people

Bucine villa

6 bedrooms / 7 bathrooms / sleeps 12

Responds fast! avg. 49 minutes

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Price per night from

$644

Luxury villa Il Santo

Buonconvento villa

6 bedrooms / 9 bathrooms / sleeps 14

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Price per night from

$3,889

Luxury villa Casina

Taverne d'Arbia villa

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$579

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Price per night from

$1,414

Castello di Tocchi Villa Sleeps 27 with Pool Air Con and WiFi - 5247841

San Lorenzo a Merse villa

14 bedrooms / 14 bathrooms / sleeps 27

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$4,913

Villa Belvedere

Poggibonsi villa

6 bedrooms / 6 bathrooms / sleeps 12

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Price per night from

$1,251

Molino del Chianti

Bucine villa

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$700

Barn Wind

Gaiole in Chianti house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$589

TuscanFlat

Siena apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$129

Casale San Martino

Monteroni d'Arbia house

5 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$1,288

Luxury villa Merlini

Rapale villa

9 bedrooms / 9 bathrooms / sleeps 18

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Price per night from

$1,334

Luxury villa Olivia

Castellina In Chianti villa

5 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$2,114

Monteluco Villa Sleeps 8 with Pool Air Con and WiFi - 5226824

Castagnoli villa

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$640

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rentals in Montepulciano

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