Vacation Rentals & Villas in Montepulciano

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3,407 Houses

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

Match: Private outdoor pool (unheated) Satellite TV Staffed property Trampoline

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Price per night from

$1,614

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Satellite TV Staffed property Trampoline

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Price per night from

$1,228

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated) Satellite TV Staffed property Trampoline

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Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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Price per night from

$135

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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Price per night from

$574

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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Price per night from

$512

Villa Brolio Quinto,exclusive use,secluded with large park and pool.

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Satellite TV, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$492

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Satellite TV, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$1,354

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$436

Casale degli Olivi

San Giovanni del Pantano farmhouse

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$807

Farm Beautiful Braid

Cannara farmhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$418

Wonderful private villa 12 people, swimming pool

San Terenziano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$601

Casavacanze Pergolino con piscina ad uso esclusivo

Acquapendente house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$73

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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Price per night from

$737

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Private outdoor pool (unheated), Satellite TV, Staffed property, Trampoline

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Price per night from

$463

Squirrel House-Cortona

Cortona house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$422

CasaRosa - Camera P. Coelho (matrimoniale)

Bettona private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$81

Loggiato apartment - Podere Casarotta

Loro Ciuffenna apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$106

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$923

Comfort under the Umbrian Sun! Pool and Air Conditioned!!

Spoleto villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$455

Villa Casolare

Perugia villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$614

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

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$614

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$702

Holiday House Villa Patty

Apecchio guest house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 34 minutes

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$123

Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$252

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$2,149

Siena Entire Tuscan Property 20P Private pool A/C Hottub wifi OutdoorKitchen

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$982

Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany

Montanare villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$553

Villa ai Cedri

Pergo farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Private outdoor pool (unheated), Satellite TV, Trampoline

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Price per night from

$404

Agriturismo il Poggio di Cantagallina

Castiglione del Lago apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$111

Agriturismo Il Torrino

Cortona villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$509

Casale at Petriolo-private pool

Casal di Pari villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 21 minutes

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$246

Private Villa with a wonderful view and private pool, close to Siena

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$442

Podere Le Cantine

Lucignano farmhouse

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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REAL CHIANTI apartm: TRULY 100% PRIVATE SWIMMING-POOL ONLY FOR YOU! Free WIFI!!!

Campoli in Chianti apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Private outdoor pool (unheated), Satellite TV, Staffed property

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Price per night from

$307

Viewing 38 of 3,407
rentals in Montepulciano

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