Vacation Rentals & Villas in Montepulciano

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DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$281

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$198

Il Tosco: your home in tuscany

Montepulciano guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$1,481

davide apartment Montepulciano

Bivio di San Biagio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$118

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I Tetti Sulla Valle - nel cuore di Montepulciano

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Housekeeping Included

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Price per night from

$111

relax in the countryside with swimming pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Housekeeping Included

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Price per night from

$118

Gues tHouse del Corso

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$161

Appartement for 2 ppl. with shared pool and terrace at Montepulciano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$162

Apartement for 2 ppl. with shared pool and terrace at Montepulciano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 50 minutes

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Price per night from

$203

Podere Monti

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$1,358

Farmhouse Olimpia in Montepulciano, apartment furnished , pool, wifi

Acquaviva di Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Housekeeping Included, Safe

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Price per night from

$111

Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$149

Holiday Resort in Montepulciano M,,air conditioning,swimmingpool,wine tasting

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$142

Lovely home of Olimpia in Montepulciano, wifi, wine and bikes, music and termal

Montepulciano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$124

Tenuta di Argiano in Montepulciano, apartment, pool, wifi, winery, trekking

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$105

Tenuta di Argiano in Montepulciano, apartment, winery, pool, wifi

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$105

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

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Price per night from

$1,235

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

$1,033

Tuscany Villa PODERE MONTI

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$1,394

La Casina Toscana, central with parking and wi-fi

Montepulciano cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$142

Great rentals within 20 miles that match your search

Villa del Falco - Poggio Cennina Country Resort

Bucine villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$700

Villa della Volpe - Poggio Cennina Country Resort

Bucine villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$700

Casa dell'Istrice - Poggio Cennina Country Resort

Bucine house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$662

Casa della Lepre - Poggio Cennina Country Resort

Bucine house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$662

Casa del Merlo - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$467

Casa del Lupo - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$467

Casa della Donnola - Poggio Cennina Country Resort

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$285

Casa del Cinghiale - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$467

Casa del Riccio - Poggio Cennina Country Resort

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$285

Casa del Tasso - Poggio Cennina Country Resort

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$285

GH Paradiso - Apartment - Split Level (C)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$186

GH Paradiso - Large 2 Bedrooms Apartment (B)

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$186

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$124

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$716

GH Paradiso - 2 Bedrooms Apartment (A)

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$186

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!

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Price per night from

$1,975

antica fonte resort

Gallena hotel apartment

  • 28 bedrooms
  • 40 bathrooms
  • sleeps 50

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Private secluded retreat in the Chianti hills between Siena and Florence

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$585

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