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Vacation Rentals & Villas in Montepulciano

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1,036 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

5 bedrooms / 5 bathrooms / sleeps 12

Match: Private outdoor pool (heated) Staffed property Trampoline

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Price per night from

$782

Todi/Collazzone agriturismo RIPA del PAVONE

Collazzone farmhouse

6 bedrooms / 8 bathrooms / sleeps 14

Match: Private outdoor pool (heated) Staffed property Trampoline

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Price per night from

$391

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

10 bedrooms / 12 bathrooms / sleeps 20

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Family winery in the Chianti Classico area with B&B "Apt PILU"

Greve in Chianti apartment

2 bedrooms / 2 bathrooms / sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$324

Apartment with garden tested in Agriturismo

Asciano apartment

2 bedrooms / 1 bathroom / sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$142

agriturismo podere poggio mendico

Arezzo farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$324

Gorgoli, luxury apartment at Fattoria Pogni

Marcialla farmhouse

2 bedrooms / 2 bathrooms / sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$203

Brigolante Guest Apartments

Assisi farmhouse

1 bedroom / 1 bathroom / sleeps 4

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Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$279

Terrasole Apartment, luxury stay at Fattoria Pogni

Marcialla farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$214

Poggio ai Falchi, beautiful first floor apartment in the country side

Marcialla farmhouse

2 bedrooms / 2 bathrooms / sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$195

Tramonto, a romantic gate away at Fattoria Pogni

Marcialla apartment

1 bedroom / 1 bathroom / sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$130

Pomantello 2

Torre Alfina apartment

3 bedrooms / 2 bathrooms / sleeps 8

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$298

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$88

Amazing studio apartment surrounded by Chianti hills

Marcialla farmhouse

1 bedroom / 1 bathroom / sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$130

Nappolaio, 1 bedroom super cozy apartment at Fattoria Pogni

Marcialla farmhouse

1 bedroom / 1 bathroom / sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$123

La Francigena B&B

Staggia Senese apartment

2 bedrooms / 1 bathroom / sleeps 7

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Apartment Juliet

Torre Alfina apartment

1 bedroom / 1 bathroom / sleeps 3

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$98

chalet marialuana

Montespertoli chalet

1 bedroom / 1 bathroom / sleeps 3

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$110

Casale panoramicissimo con piscina S. Damiano

Todi villa

2 bedrooms / 2 bathrooms / sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$143

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

9 bedrooms / 6 bathrooms / sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$712

VILLA TALCIONA

Poggibonsi apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 21 minutes

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$175

Stunning private villa in Chianti wellness

Castelnuovo Berardenga villa

8 bedrooms / 5 bathrooms / sleeps 16

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$537

Wellness Center Casanova

San Quirico d'Orcia b&b

1 bedroom / 3 bathrooms / sleeps 2

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$156

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

15 bedrooms / 15 bathrooms / sleeps 33

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,647

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

7 bedrooms / 7 bathrooms / sleeps 14

“Outstanding Tuscany Villa” We stayed at Podere Patrignone for 7 days in October 2012. We were a party of 4 couples from the USa. We had done a lot of research in finding a villa that would provide what we thought would be the ultimate Tuscan experience; Podere Patrignone did that. We stayed in the main house and occupied 4 of the bedrooms. The accommodations were great, much like staying at a friend's country home. Each bed room has its own private bath accessed from the bedroom, not a hallway. There is a large, fully equipped kitchen where we spent most nights playing cards, reading, etc. We purchased breakfast 3 days and participated in the dinner one day. All meals were great and highly recommended. We went to many of the restaurants suggested by our hosts and I must say they were all excellent. My recommendation is to follow their recommendations; they will not steer you wrong. Speaking of our hosts, they were great. Simon and Verity are great hosts and were always available to make suggestions, etc. We ran into them most days somewhere on the property and they always had time to stop and chat for a bit, even though we knew they were busy. When reading the reviews on Podere Patrignone you will note almost all are very positive but that a few are not as positive. Remember this - you cannot please everyone. If you are looking for a authentic Tuscany villa, great hosts and an excellent location, you will love Podere Patrignone. All of us in our party did. My wife and I still talk about our week's stay and would love to return some day.

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$591

B & B Il Sognatore Bed and Breakfast in Perugia rooms with original pool theme

Ponte San Giovanni b&b

3 bedrooms / 3 bathrooms / sleeps 7

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$104

Lovely apartment in farmhouse, private pool, beautiful garden, quiet position

Brolio farmhouse

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 34 minutes

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$234

the Mill house Photos

Certaldo apartment

3 bedrooms / 2 bathrooms / sleeps 8

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$540

il Paluffo Forno House Luxury apartment

Certaldo apartment

2 bedrooms / 2 bathrooms / sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$398

the Tower House Photos

Certaldo apartment

3 bedrooms / 3 bathrooms / sleeps 8

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$605

il Paluffo Stillo House

Certaldo apartment

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$489

Agriturismo Pian del Gallo 3

Greve in Chianti farmhouse

2 bedrooms / 2 bathrooms / sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$169

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

5 bedrooms / 4 bathrooms / sleeps 12

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$278

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

1 bedroom / 1 bathroom / sleeps 2

“Very Romantic and Relaxing” Podere Patrignone, is a very well managed holiday/vacation destination. Simon and Verity (owners), went to great lengths to make sure ours and other guests stays we're relaxing and enjoyable. Always available, but rairly needed, they have created an "old world charm" and very natural feel to their quiet olive orchard. Whether it's a romantic getaway (ours was our 10th wedding anniversary), a quiet place to retreat and relax, or just a quaint Tuscan "centrally" located place to stay, we highly recommend it. Everything on their website was exactly as advertised! What isn't as highly advertised, but left to us to tell about, is the care and passion Simon and Verity have for making this such a special place to stay. And don't miss the weekly group dinner. Verity goes all out for that, and it's a delicious Tuscan style feast with a wonderful group of people! We can't wait to return!

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$198

Villa Nobile

Cortona villa

9 bedrooms / 6 bathrooms / sleeps 18

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,107

Collelungo Farm Maremma

Magliano in Toscana farmhouse

1 bedroom / 1 bathroom / sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$59

VILLA FEBEA, PRIVATE VILLA WITH HEATED SWIMMING POOL AND CHURCH

Chiusi villa

12 bedrooms / 12 bathrooms / sleeps 22

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$556

Viewing 38 of 1,036
rentals in Montepulciano

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