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Pienza Rentals

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From $1350 per night (USD)
VRBO
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Bedrooms:
10
Bathrooms:
9
Sleeps:
20
Entire VILLA at your 100% PRIVATE disposal with 9 Bedrooms, 11 Bathrooms (9 en-suite), PANORAMIC equipped POOL, private ...
From $1350 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Cosy apartment for 5 guests with WIFI, pool, TV and panoramic view, close to Montepulciano
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units ...
From $140 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Lovely apartment for 6 people with WIFI, pool and panoramic view, close to Montepulciano
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units ...
From $177 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Beautiful villa for 8 people with WIFI, private pool, TV and panoramic view, close to Montepulc...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Independent portion of a stone farmhouse dating back to the 15th century. This property, which has been, completely rest ...
From $386 per night (USD)
Expedia
From $119 per night (USD)
VRBO
Beautiful apartment for 4 guests with pool, WIFI, TV and panoramic view, close to Montepulciano
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcoming farmhouse situated in panoramic location in the beautiful area of Val D’Orcia. This property comprises 4 units ...
From $119 per night (USD)
VRBO
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Expedia
Country house with private Swimming pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Villa Apparita is a typical Tuscan farm from the 1800s in a panoramic position in the heart of Tuscany, in the municipal ...
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Expedia
From $108 per night (USD)
VRBO
Amazing Panorama in Monticchiello
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Villa PoliFlora Panorama is an independent apartment on the first floor overlooking the famous cypresses of Monticchiell ...
From $108 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Elegant apartment with garden view and rooftop terrace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Close to ecotours, rock climbing, and more, this pet-friendly apartment brings it all within reach. Thanks to the con ...
From $160 per night (USD)
Expedia
From $481 per night (USD)
VRBO
House / Villa - Pienza
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
(Text automatically translated) In Val d'Orcia where olive trees are lit up with silvery reflections, where the relation ...
From $481 per night (USD)
VRBO
From $164 per night (USD)
Expedia
Casa Bonari, amazing Tuscan view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casa Bonari is located in Monticchiello, in Val d’Orcia, the heart of Tuscany. It’s an indipendent apartment inside a co ...
From $164 per night (USD)
Expedia
From $737 per night (USD)
VRBO
Private Villa with private pool, A/C, internet, TV, patio, panoramic view, close to Montepulciano
Bedrooms:
9
Bathrooms:
7
Sleeps:
14
Conveniently located 2 km (1 mi) from Monticchiello, Italy in the tourist area "Orcia Valley" and only 14 km (9 mi) from ...
From $737 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Friends of Tuscany Ltd. takes care of every detail of your villa booking, providing personalized information to ensure y ...
From $308 per night (USD)
Expedia
$\Il Focolare\ Superior Apartment in Monticchiello$
From $117 per night (USD)
VRBO
\"Il Focolare\" Superior Apartment in Monticchiello
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The house is located in the small medieval village of Monticchiello, within the imposing city walls. Immersed in the cla ...
From $117 per night (USD)
VRBO
From $1009 per night (USD)
Expedia
Villa in Monticchiello with pool,Airconditioning,BBQ,Garten,Table tennis,sleep14
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Set in a one of the most beautiful areas of Tuscany, near Monticchiello, this stunning villa enjoys a breath-taking view ...
From $1009 per night (USD)
Expedia
From $151 per night (USD)
VRBO
A very comfortable apartment in Tuscan style
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The apartment named "Pienza" in Monticchiello is located on the first floor of Villa PoliFlora, with an exclusive view o ...
From $151 per night (USD)
VRBO
From $2442 per night (USD)
VRBO
Dimora Buonriposo Pienza Country House
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
A short distance from ecotours, wildlife walks, and more, this welcoming vacation home lets you experience it all. Ju ...
From $2442 per night (USD)
VRBO
$Apartment \Agriturismo Il Casato Mag-il Vaglio\ with Mountain View, Terrace and Wi-Fi$
From $626 per night (USD)
VRBO
Apartment \"Agriturismo Il Casato Mag-il Vaglio\" with Mountain View, Terrace and Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Pienza, in the heart of the Val d'Orcia, this stone villa is just 5 minutes from the historic center, which y ...
From $626 per night (USD)
VRBO
From $874 per night (USD)
VRBO
Villa Fontana
Bedrooms:
9
Bathrooms:
7
Sleeps:
14
Ideal for a luxury holiday combined with great hospitality.The extensive lawn is mainly grass to maintain the open space ...
From $874 per night (USD)
VRBO
From $822 per night (USD)
VRBO
Affittacamere Maria Gabriella, B&B and Holiday Home in Val d'Orcia
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Ashort way from Porta St. Agata, the main gate to the medieval village of Monticchiello, Guido is glad to welcome you i ...
From $822 per night (USD)
VRBO
From $4250 per night (USD)
VRBO
Stunning Refurbished Farmhouse With All Luxury Amenities & Staff Included
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
This beautifully restored villa sits in an ideal location in the hills outside of Pienza in the famed, world heritage pr ...
From $4250 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Holiday house Pienza for 1 - 10 persons with 4 bedrooms - Twin house
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
ED Refnr. 2899603 This lovely holiday home in Val d’Orcia in the Middle Ages was probably a resting place for pilgrims ...
From $339 per night (USD)
VRBO
From $964 per night (USD)
VRBO
Luxury Tuscan villa, spectacular views, beautiful pool and garden.
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Surrounded by lovely gardens in 29 hectares (70 acres) of unspoilt, peaceful & private woodland, olive groves and farmla ...
From $964 per night (USD)
VRBO
From $1984 per night (USD)
VRBO
Iperbole country house, between Pienza and Montepulciano
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
The house sleeps comfortably 9 people in 4 double bedrooms and 1 single ( full bed) , each with its own bathroom. .The ...
From $1984 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Villa with panoramic views of Pienza and Val d'Orcia
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Close to ecotours, wildlife walks, and more, this family-friendly vacation home brings it all within reach. Art Studi ...
From $440 per night (USD)
VRBO
From $221 per night (USD)
VRBO
Ginestra apartment overlooking the Val d'Orcia
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A short distance from ecotours, wildlife walks, and more, this family-friendly apartment lets you experience it all. ...
From $221 per night (USD)
VRBO
From $814 per night (USD)
VRBO
Pienza villa rental with pool
Bedrooms:
9
Bathrooms:
7
Sleeps:
14
Summary: This is a stunning 7 bedroom Pienza villa rental which can work well for either one large group or two smaller ...
From $814 per night (USD)
VRBO
From $455 per night (USD)
VRBO
Your piece of Heaven: Pure Relax in a charming & historical Villa
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
The old cottage is situated on top of the hill that is in front of the beautiful town of Pienza, a UNESCO World Heritage ...
From $455 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Nice apartment in villa for 2 guests with WIFI, A/C, close to Montepulciano
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Maria Gabriella Home & Cottage is a beautiful holiday home with WiFi internet and air conditioning. Maria Gabriella Home ...
From $176 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Cosy apartment in villa for 6 people with WIFI, A/C, TV and veranda, close to Montepulciano
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Maria Gabriella Home & Cottage is located in the centre of Monticchiello, Italy and only 9 km (5 mi) from Montepulciano ...
From $351 per night (USD)
VRBO
From $469 per night (USD)
Expedia
Wonderful private villa for 8 people with A/C, WIFI, TV and veranda, close to Montepulciano
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Vacation rental Maria Gabriella Holiday Home In Monticchiello is a nice property (600 sq m) that includes air condition ...
From $469 per night (USD)
Expedia
From $937 per night (USD)
VRBO
Villa Fonte Siena
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
The villa in Monticchiello has 6 bedrooms and has capacity for 12 people. Villa Fonte Siena is located in Monticchiello, ...
From $937 per night (USD)
VRBO
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Expedia
Dolce Pienza - Modern Home in the Historic Center
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nestled in Pienza, this 2-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and the outdo ...
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Expedia
$Apartment \Agriturismo Il Casato Mag-il Giogo\ with Mountain View, Terrace and Wi-Fi$
From $818 per night (USD)
VRBO
Apartment \"Agriturismo Il Casato Mag-il Giogo\" with Mountain View, Terrace and Wi-Fi
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in Pienza, in the heart of the Val d'Orcia, this stone villa is just 5 minutes from the historic center, which y ...
From $818 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Podere Fontebernardi, authentic Tuscan farmhouse overlooking Pienza.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Close to ecotours, birdwatching, and more, this pet-friendly vacation home brings it all within reach. Jump into your ...
From $479 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Beautiful apartment for 4 people with A/C, WIFI and TV, close to Montepulciano
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Monticchiello Apartment With Garden, Wifi, Pienza, is a beautiful stone building (85 sq m) with WiFi internet and air c ...
From $182 per night (USD)
VRBO
From $1013 per night (USD)
Expedia
Podere Manafiore - historical villa with swimming pool
Bedrooms:
7
Bathrooms:
6
Sleeps:
10
The estate, renovated to revive its ancient splendor while maintaining its distinctive atmosphere, can accommodate up to ...
From $1013 per night (USD)
Expedia
Click For Pricing
VRBO
Modern Farmhouse in Pienza With Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
While you're here, you can enjoy all the comforts of home and more, including an oven and free WiFi, as well as digit ...
Click For Pricing
VRBO
From $531 per night (USD)
VRBO
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
The farmhouse has a composite structure. Its oldest part is the watching tower with a scarp wall. It was built in the an ...
From $531 per night (USD)
VRBO
From $224 per night (USD)
VRBO
Villa Arpicella Pienza Siena Italy Tuscany, a stunning, green, peacefull corner
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
SURROUNDINGS Villa Arpicella is within a few miles of the historic and artistic villages of the Val D'Orcia in the south ...
From $224 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Podere Osteria In Pienza, Tuscany
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Property for exclusive use "Podere Osteria” is a country house which was originally one of the first examples of Europe ...
From $317 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Stunning private villa with private pool, WIFI, TV, veranda, panoramic view, close to Montepulciano
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming former stone barn with private pool situated in peaceful location south of Siena, amidst the beautiful hills of ...
From $216 per night (USD)
VRBO
From $1019 per night (USD)
Expedia
Luxurious 5-bedroom villa in charming Castelmuzio, Val d'Orcia wine region
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Nestled within the medieval hilltop of Castelmuzio, Casa Nobile is an elegant and sophisticated town house that sits on ...
From $1019 per night (USD)
Expedia
From $4697 per night (USD)
VRBO
Villa Il Beneficio
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
The house in Montepulciano has 6 bedrooms and has capacity for 12 people. Together with all modern technology the villa ...
From $4697 per night (USD)
VRBO
From $258 per night (USD)
VRBO
Villa Mazzi, hospitality and good taste vacation in the Tuscan countryside
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
The structure consists of four apartments, newly renovated with 2/4 beds for a total of 14 beds. With independent entran ...
From $258 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Private Tuscan Farmhouse with Stunning Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in the captivating hills of the Val d'Orcia region, between the historic towns of Montisi and Castelmuzio, lies ...
From $309 per night (USD)
VRBO
From $558 per night (USD)
VRBO
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
The farmhouse has been completely restored in 2009, according to the principles of bio-architecture; employing building ...
From $558 per night (USD)
VRBO
From $833 per night (USD)
VRBO
Charming Villa with private pool between Pienza and Montepulciano
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Villa Il Gelso is one of the three Villas of Casali Cellini . Careful restoration finished in May 2015 , using original ...
From $833 per night (USD)
VRBO
From $760 per night (USD)
VRBO
Casal d'Asso In San Giovanni d'asso, Tuscany
Bedrooms:
5
Bathrooms:
4
Sleeps:
7
Property for exclusive use Casale d’Asso is an ancient 18th-century holiday house, recently restored, on the edge of sma ...
From $760 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Apartment 'L'uscio' with Mountain View, Shared Pool and Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
With a view of the mountain, the holiday apartment L'uscio in Chianciano Terme is perfect for a relaxing holiday. The 90 ...
From $231 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Apartment 'Granaio' with Mountain View, Shared Pool and Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
With a view of the mountain, the holiday apartment Il granaio in Chianciano Terme is perfect for a relaxing holiday. The ...
From $269 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
In Chianciano Terme, the holiday apartment La loggia offers an excellent view of the mountain. The 80 m² property consis ...
From $230 per night (USD)
VRBO
From $1886 per night (USD)
Expedia
Villa Pianoia – Elegance and Historic Charm for Groups and Special Events
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
Nestled in the heart of Tuscany, Villa Pianoia is a historic residence surrounded by lush greenery, located between Mont ...
From $1886 per night (USD)
Expedia
From $2044 per night (USD)
VRBO
AMORE RENTALS - Villa Olimpia with Pool, Garden, Ideal for Weddings
Bedrooms:
8
Bathrooms:
8
Sleeps:
19
This sumptuously designed and decorated Tuscan country house, set in a prime hilltop location in the Val d’Orcia, is an ...
From $2044 per night (USD)
VRBO
From $2165 per night (USD)
Expedia
AMORE RENTALS - Villa Valle with Pool, Garden, Ideal for Weddings
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Enjoy views over the rolling hills of the Val d’Orcia in Tuscany from this sensitively restored large group villa with h ...
From $2165 per night (USD)
Expedia
$Villa \Privata Locanda In Tuscany\ with Private Pool, Private Terraces & Wi-Fi$
From $6444 per night (USD)
VRBO
Villa \"Privata Locanda In Tuscany\" with Private Pool, Private Terraces & Wi-Fi
Bedrooms:
9
Bathrooms:
9
Sleeps:
24
The villa "Privata Locanda in Tuscany" is located in Castiglione D'Orcia and is perfect for an unforgettable holiday wit ...
From $6444 per night (USD)
VRBO
From $903 per night (USD)
Expedia
Villa 'Country House Podere I Prati' with Private Pool, Private Garden and Wi-Fi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in Chianciano Terme, Tuscany, Country House Podere I Prati is a 350 sqm villa that welcomes up to 8 guests in 4 ...
From $903 per night (USD)
Expedia
From $4315 per night (USD)
VRBO
Private Villa with A/C, hot tub, private pool, WIFI, sauna, TV, veranda, close to Montepulciano
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Villa Bartolomeo is a nice stone building (400 sq m) with WiFi internet, air conditioning and private pool. The propert ...
From $4315 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Casa Ora d’Oro - PANORAMIC VIEWS / POOL / PRIVATE GARDEN
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our villa is nestled in the rolling hills of Tuscany, located in the Val d’Orcia and Crete Senesi region. Located in the ...
From $425 per night (USD)
Expedia
Click For Pricing
VRBO
Zampugna
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a refrigera ...
Click For Pricing
VRBO
From $4875 per night (USD)
VRBO
Montepulciano villa rental
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Summary: Villa Bene is a beautiful Montepulciano villa rental. Recently restored, original 16th century features blend s ...
From $4875 per night (USD)
VRBO

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Pienza Rentals

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Results: 60 Rentals