Vacation Rentals & Villas in Montepulciano

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1,276 Houses

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Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool Housekeeping Included Staffed property Trampoline

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Price per night from

$738

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$86

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$379

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$576

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Heated pool, Housekeeping Included, Trampoline

3 of 4 filters match

Price per night from

$437

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Heated pool, Housekeeping Included, Trampoline

3 of 4 filters match

Price per night from

$555

Suite CielAzzurro

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$74

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$74

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$465

VILLA TALCIONA

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Heated pool, Housekeeping Included, Trampoline

3 of 4 filters match

Price per night from

$191

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$1,106

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$1,832

Tenuta I Terzi d Ombrone

Poggi del Sasso villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$3,233

Fattoria Quercia al Poggio - Apartment Proneta 1

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$218

#la Ghibellina Montalcino

Montalcino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$123

B & B THE OLD Lieutenancy Suite Double

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 13 minutes

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$99

the garden of the Etruscans

Chiusi villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 59 minutes

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$111

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Housekeeping Included, Heated pool, Staffed property, Trampoline

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B&B Le Storie di Pietra - Deluxe Room-

Todi private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$105

B&B Le Storie di Pietra - Cozy Room -

Todi private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$86

Fattoria Quercia al Poggio - Apartment Cappella 3

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$233

Lacasadicampagna Agricola

Collevalenza apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$80

comfortable room by andrea

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$62

Fantastic apartment in a Tuscan farmhouse

San Rocco a Pilli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$197

the garden of the Etruscans

Chiusi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 59 minutes

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$197

The Granary, villa with pool and heated spa

San Venanzo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$234

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$2,107

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$3,588

Villa Rovicciano, sleeps 16+4. Family reunions, cooking service, heatable pool

Castel Ritaldi villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$1,475

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

3 of 4 match: Trampoline, Heated pool, Housekeeping Included, Staffed property

3 of 4 filters match

Price per night from

$1,033

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Staffed property, Housekeeping Included, Trampoline

2 of 4 filters match

Price per night from

$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Staffed property, Housekeeping Included, Trampoline

2 of 4 filters match

Price per night from

$160

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

2 of 4 filters match

Price per night from

$308

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

2 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

2 of 4 filters match

Price per night from

$308

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Heated pool, Housekeeping Included, Staffed property, Trampoline

2 of 4 filters match

Price per night from

$136

Deliziosa romantica camera

Asciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$62

Fattoria Quercia al Poggio - Apartment Cappella 4

Barberino Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$99

Fattoria Quercia al Poggio - Apartment Cappella 2

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Housekeeping Included, Staffed property

2 of 4 filters match

Price per night from

$182

Viewing 38 of 1,276
rentals in Montepulciano

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