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98 Houses

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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

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Price per night from

$1,027

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms
2 bathrooms

sleeps 5

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$208

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom
1 bathroom

sleeps 4

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$171

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$185

Studio "Rustic" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom
1 bathroom

sleeps 2

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$128

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom
1 bathroom

sleeps 4

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$171

Studio "Borghetto" at The House of the Oaks - Montepulciano

Montepulciano studio

Studio
1 bathroom

sleeps 2

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Price per night from

$128

Tenuta Senese Tenuta Senese

Montepulciano house

5 bedrooms
6 bathrooms

sleeps 10

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Price per night from

$643

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

6 bedrooms
5 bathrooms

sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

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Price per night from

$1,044

TASKO

Montepulciano villa

5 bedrooms
9 bathrooms

sleeps 9

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Price per night from

$1,228

Casa Dei Ro.Gi. - Montepulciano - Tuscany

Abbadia di Montepulciano house

3 bedrooms
2 bathrooms

sleeps 4

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$79

Tuscany Villa in Montepulciano,Free Parking,Free Wi-fi,view of valley

Bivio di San Biagio villa

2 bedrooms
2 bathrooms

sleeps 7

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Price per night from

$307

Il Molinaccio 14+2, Emma Villas

Cervognano villa

7 bedrooms
8 bathrooms

sleeps 16

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Price per night from

$1,008

Great rentals within 20 miles that match your search

Stones of the ancient village

San Lorenzo a Merse house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$129

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

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Price per night from

$307

Poggio alla Rocca - SUN

Casale di Pari house

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$614

detached house in the small hamlet of 4 buildings

Figline e Incisa Valdarno house

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$99

Muricce House

Mercatale Valdarno apartment

3 bedrooms
2 bathrooms

sleeps 8

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Inquire for Rates

Casa Azzurra

Barberino Val d'Elsa house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$185

Casa Mia In Chianti, Close to Florence & Siena.

Tavarnelle Val di Pesa apartment

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$99

Siena country house, private pool.

Quercegrossa villa

5 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$702

Borgo La Bagnaia #Villa Sarageto

San Giovanni d'Asso villa

4 bedrooms
4 bathrooms

sleeps 7

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$860

Gated Luxury Estate "LaChiusa" Prime Chianti Classico! Exquisite Privacy & Views

Siena farmhouse

4 bedrooms
3 bathrooms

sleeps 6

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$1,426

Poggerina luxury private villa with stunning view

Greve in Chianti villa

4 bedrooms
4 bathrooms

sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

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Price per night from

$614

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

9 bedrooms
6 bathrooms

sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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Price per night from

$1,228

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.

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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!

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Price per night from

$608