Vacation Rentals & Villas in Montepulciano

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55 Houses

Agriturismo I Fuochi

Valiano farmhouse

11 bedrooms / 9 bathrooms / sleeps 22

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$1,067

Apartment Il Ciliegio

Valiano apartment

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$164

Farmhouse Il Fienile

Montepulciano farmhouse

7 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$176

Great rentals within 20 miles that match your search

Villa Le Bolli: a vacation like at your home!

Radicondoli villa

12 bedrooms / 14 bathrooms / sleeps 36

“A beautiful place to spend great moments with friends and family” We have been three families, a couple and some friends arriving on their own. It was one of the most relaxing, funny and wonderful holiday we have ever spent. The kids loved their time at the pool, the garden, with dart, billiard, ping-pong and table soccer and of course with the cat "Luigi". We adults had lots of time for chatting, laughing, joint cooking and eating, relaxing and some sports. The professional and big kitchen is a real asset. Albeit the nearby very fine and cosy restaurants, we usually preferred staying among us in the villa. Both, in sun shine and rain, the villa offers all you need for a great time in the big group (a big salon with open fire, several living and dining rooms indoor, the big and well-kept garden, main terrace, barbeque and pool outdoors). There are however also enough spaces to retire to, such as a hammock below a beautiful old oak, hidden benches in the garden, comfortable sofas here and there, and of course the spacious sleeping rooms, each with individual features and great views over the Tuscan landscape. We definitely can recommend this place!

Responds fast! avg. 55 minutes

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Price per night from

$1,015

Tuscan/Siena Villa 22 pax Fenced Pool, Hot tub, WiFi,A/C, Outdoorkitchen

Siena villa

11 bedrooms / 11 bathrooms / sleeps 22

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Price per night from

$698

Agriturismo Casa Pietraia

Certaldo farmhouse

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$443

Restored Barn - country home

Quercegrossa barn

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$108

Farmhouse with private garden and pool in Tuscany

Tavarnelle Val di Pesa farmhouse

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 47 minutes

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Price per night from

$127

Il Bel Canto Bed and Breakfast

Radicondoli apartment

3 bedrooms / / sleeps 9

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Price per night from

$253

IL GAVILLACCIO Residence

Figline e Incisa Valdarno apartment

2 bedrooms / 4 bathrooms / sleeps 5

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Price per night from

$190

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Price per night from

$270

Tenuta La Campana

Crete Senesi farmhouse

6 bedrooms / 7 bathrooms / sleeps 12

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Responds fast! avg. 3 hours 40 minutes

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Price per night from

$396

Private Tuscan Villa

Radicondoli villa

12 bedrooms / 13 bathrooms / sleeps 24

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Poggerina luxury private villa with stunning view

Greve in Chianti villa

4 bedrooms / 4 bathrooms / sleeps 8

“A beautiful villa in an amazing place, wonderful nice owner.” We stayed in the Villa late September 2014. The weather was nice, but not warm enough for the pool. We had amazing bio garden tomatoes every day, and loved the beautiful garden and house. Emanuele, was amazing. Helped a lot, guiding us and explaining where to go etc. The villa is clean, big, with amazing view of the mountains and the vineyards that grow just around the corner. The rooms are bright and the furniture is comfortable. The kitchen is fully equipped with any thing you need to cook an amazing dinner every day. There are 3 bathrooms with shower or tube, and one bathroom with toilet only. The upper room is quite and nice, and suitable for children mostly. We had a wonderful week in Chianti, and we will be back again. Thank you Emanuele.

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$265

Responds fast! avg. 3 hours 40 minutes

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Price per night from

$361

Room Apartment A with pool near Siena

Isola d'Arbia farmhouse

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$253

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

$1,279

Responds fast! avg. 2 hours 37 minutes

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Price per night from

$757

Siena, Farmhouse villa with outdoor swimmingpool near Siena, Tuscany, Italy

Murlo villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 31 minutes

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Price per night from

$182

A terrace on siena

Sovicille villa

5 bedrooms / 5 bathrooms / sleeps 14

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Vernianello - Type B

Poggibonsi farmhouse

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$133

Amazing stay in the heart of Tuscany, Chianti area

Gaiole in Chianti house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$265

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

$1,570

Il castagno

Radicondoli apartment

4 bedrooms / 2 bathrooms / sleeps 9

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Price per night from

$177

. IL GLICINE - Enjoy the Tuscan - free WI-FI

Monteguidi apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$91

Ghezzi-Farm App. Gisella

Pergine Valdarno house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$251

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

$1,704

A part of a beautiful mansion with view of the Chianti Classico hills

Montefiridolfi house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$140

Peaceful Holiday Home with Pool in Montefiridolfi Italy

Montefiridolfi villa

3 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$244

VILLA CALCINAIA - SAN PIERINO

Greve in Chianti farmhouse

6 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$251

Cerbaia Rock Country Resort

Sovicille villa

8 bedrooms / 8 bathrooms / sleeps 16

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Price per night from

$1,130

Poggio Cuccule

Moncioni house

11 bedrooms / 8 bathrooms / sleeps 22

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Price per night from

$585

La Ginestra

Radicondoli apartment

1 bedroom / 2 bathrooms / sleeps 4

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Price per night from

$113

Charming Nido in Chianti Shire

Gaiole in Chianti house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$88

A Rustic mansard overlooking the Tuscan hills

Greve in Chianti penthouse

4 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 3 hours 11 minutes

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Price per night from

$277

A-Room Apartment with pool near Siena

Isola d'Arbia farmhouse

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$251

Cavernous (SGI420)

Castel San Gimignano house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$166

Viewing 38 of 55
rentals in Montepulciano

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