Vacation Rentals & Villas in Montepulciano

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170 Houses

Villa Nobile, Luxury Tuscan Home, Walk to Town

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 1 hour 50 minutes

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$1,190

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

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 23 minutes

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$149

Villa Iris - Perfect for families or group of friends

Montepulciano apartment

3 bedrooms / 3 bathrooms / sleeps 5

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$213

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

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$112

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

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$124

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 23 minutes

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$87

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

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$112

Le Manzinaie - Glicine - Romantic apartment in Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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$118

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

Montepulciano studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$87

Tenuta Senese Tenuta Senese

Montepulciano house

5 bedrooms / 6 bathrooms / sleeps 10

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$533

Le Manzinaie - Limoni - Dream apartment in Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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$118

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

$940

Le Manzinaie - Rose - Magic apartment for couples

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$118

Le Manzinaie - Edera - Ideal for couple in love

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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$118

Le Manzinaie - Girasole - Perfect holiday in Tuscany

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$154

Agriturismo La Terra, Casa Carla a romantic room

Valiano farmhouse

1 bedroom / 1 bathroom / sleeps 2

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$99

Agriturismo La Terra, Casa Simonetta

Valiano farmhouse

2 bedrooms / 2 bathrooms / sleeps 4

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$204

TASKO

Montepulciano villa

5 bedrooms / 9 bathrooms / sleeps 9

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Price per night from

$1,235

Casa Dei Ro.Gi. - Montepulciano - Tuscany

Abbadia di Montepulciano house

3 bedrooms / 2 bathrooms / sleeps 4

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$80

Great rentals within 20 miles that match your search

Villa San Gimignano-apartment 1 to 6 people

Chiusdino apartment

3 bedrooms / 2 bathrooms / sleeps 6

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$132

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

$259

Nice apt with pool access & terrace

Monte San Savino apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$198

Casale Barberino Casale Barberino for 12

Barberino Val d'Elsa apartment

6 bedrooms / 6 bathrooms / sleeps 12

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$447

Agriturismo il Girasole-apartment Attic

San Gimignano apartment

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$105

Villa with private pool in the heart of Tuscany

Pieve A Presciano villa

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$840

Beautiful apt with pool access

San Gimignano apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$137

Panoramic Villa in Crete Senesi

Asciano villa

4 bedrooms / 3 bathrooms / sleeps 10

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$371

Podere Margherita Podere Margherita

Greve in Chianti villa

6 bedrooms / 7 bathrooms / sleeps 12

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$485

Apartment (F)in the center of Tuscany with Swimming Pool/Whirlpool/Tennis court.

Montecastelli Pisano apartment

1 bedroom / 1 bathroom / sleeps 4

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$93

Il Frantoio apt. at La Vecchia Greve with shared pool and wifi

Greve in Chianti apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 59 minutes

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$81

Restored Barn - country home

Quercegrossa barn

1 bedroom / 1 bathroom / sleeps 3

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$106

Authentic 3 Bedroom Farmhouse

Castellina In Chianti b&b

3 bedrooms / 2 bathrooms / sleeps 8

“The best and most relaxing vacation ever” As two couples, Poderi Val Verde's restored farmhouse was indeed rustic, but was perfect for us: adjoining suites each with a kitchen and patio overlooking the stunning grounds, one with a living room and fireplace, the other with a fantastic sunroom overlooking the grounds and pool. We stayed for our full 2 week visit and were thrilled with our choice of living on a working farm of over 200 hectares with a 350 year history. Our quarry stone home was clean, comfortable and perfectly located to facilitate our day trips to nearby villages-to neighboring Castellina in Chianti, as well as Siena, Florence, Poggibonsi, Greve, and Panzano where we participated in their annual wine festival. Around every corner of the road there was another breathtaking vista each arguably better than the last. We had our big Italian meal of the day wherever we were early in the afternoon and made a light dinner in our kitchen most evenings, eating on the patio with candle lights and wine listening to the sounds of wild boars, deer and wolves in the hillside and our hostesses' dogs keeping them all at bay. Most mornings we watched the sun rise over the valley, prepared a quick breakfast then usually stopped mid-morning for cappuccinos. Our kitchens were well equipped, however the lighting didn't meet our standards, easily solvable by task lights ... but,if that's our only complaint!!! Our hostess, Ulrike, runs the farm alone, feeds the sheep, chickens, ducks, dogs, cats and countless kittens who were always underfoot and also feeds her guests a Welcome Dinner Feast that shouldn't be missed - for the food and for the opportunity to meet new friends. Ulrike was always there to help us, make suggestions and share some wine or her homemade jams. By the end of our visit, she was no longer our hostess but a huggable friend. My well-traveled wife called it the best and most relaxing vacation of her life. When we return, we'll stay there again.

Responds fast! avg. 2 hours 39 minutes

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Price per night from

$322

Nice house with pool access & Wifi

Casole d'Elsa house

1 bedroom / 1 bathroom / sleeps 4

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$146

Holiday House "Via degli Orti"

Radicondoli house

3 bedrooms / 2 bathrooms / sleeps 6

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$93

Spacious house with pool access

Casole d'Elsa house

2 bedrooms / 2 bathrooms / sleeps 6

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$188

Apartment (A)in the center of Tuscany with Swimming Pool/Whirlpool/Tennis court

Montecastelli Pisano apartment

1 bedroom / 1 bathroom / sleeps 4

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$99

Felceto

Panzano in Chianti villa

7 bedrooms / 7 bathrooms / sleeps 13

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Price per night from

$792

- LA CASA DEI NONNI - Only you and your family

Monteguidi cottage

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$141

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rentals in Montepulciano

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