
Unione dei Comuni Valdichiana Senese Rentals
- From $234 per night (USD)
VRBO
Awesome home in Pienza
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself to a dream holiday in this enchanting holiday home with a large pool in an idyllic rural setting. This ...
From $234 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Holiday home with garden
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The detached holiday home built in 1500, was renovated in 2015 and is furnished in a luxury and typical country style. T ...
From $296 per night (USD)Expedia
- Click For Pricing
VRBO
Apartment beautiful sunset farmhouse pascianella
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
<p>Located in Trequanda, this welcoming vacation home brings it all within your reach. Thanks to the convenient onsite p ...
Click For PricingVRBO
- From $1393 per night (USD)
Expedia
Villa la Monarca 16, Emma Villas
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
This rate includes: -Utilities: electricity - water - gas for kitchen use and hot water - weekly linen, initial and fina ...
From $1393 per night (USD)Expedia
- From $1031 per night (USD)
VRBO
My Rental Homes - Villa Incanto with pool offers an amazing view of Montepulicano
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 15
Only 900 meters from the beautiful city of Montepulciano Villa Incanto is a wonderful country house with a private swimm ...
From $1031 per night (USD)VRBO
- From $1930 per night (USD)
Expedia
Villa Bravio: A characteristic and welcoming two-story villa made of stone, with Free WI-FI.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Villa Bravio is a characteristic and welcoming two-story villa made of stone. It sleeps 12 people. From Villa Bravio you ...
From $1930 per night (USD)Expedia
- From $865 per night (USD)
VRBO
My Rental Homes - Villa Monticchiello with pool and garden surrounding the property
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Villa Monticchiello is a stunning property set in one of most amazing Tuscan area Val D’Orcia protected by the UNESCO; t ...
From $865 per night (USD)VRBO
- From $347 per night (USD)
Expedia
Agriturismo Borgo Sette Tigli - apt 1
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
During the summer months, our pool is the perfect spot to cool off and take in the breathtaking views of the surrounding ...
From $347 per night (USD)Expedia
- From $505 per night (USD)
VRBO
Vacation home for 7 guests with 120m² in Cortona (271993)
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
<p>Located in Cortona, this welcoming vacation home lets you experience it all. Thanks to the convenient onsite parking, ...
From $505 per night (USD)VRBO
- From $511 per night (USD)
Expedia
Stunning private villa for 14 people with WIFI, private pool, TV and patio, close to Montepulciano
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Villa Acquaviva With Pool In Perugia is located 13 km (8 mi) from Castiglione Del Lago, Italy and only 25 km (15 mi) fro ...
From $511 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mery's House- elegant apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located just 400 meters from the historic center of Montepulciano and close to all amenities, this charming apartment fe ...
From $297 per night (USD)VRBO
- From $295 per night (USD)
Expedia
Ancient Village 7
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Located in Montepulciano, this welcoming apartment lets you experience it all. Val di Chiana is just steps away and P ...
From $295 per night (USD)Expedia
- From $678 per night (USD)
VRBO
Cozy home in Sarteano
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Look forward to an unforgettable holiday in this spacious holiday home with pool and breathtaking panoramic views. We ...
From $678 per night (USD)VRBO
- From $193 per night (USD)
VRBO
Bella Casa Toscana, a contemporary designed penthouse apartment in Tuscany.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Bella Casa Toscana, a contemporary designed penthouse apartment in Chiusi Scalo, Tuscany. The apartment featu ...
From $193 per night (USD)VRBO
- From $87 per night (USD)
VRBO
Macadamia Tuscany House - Studio apartment in the green, bordering Val d'Orcia
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>Located in Sarteano, this welcoming vacation home lets you experience it all. Val di Chiana is just a short walk away ...
From $87 per night (USD)VRBO
- From $262 per night (USD)
Expedia
Apartment 'Appartamento In Palazzo Bucelli' with Balcony and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The holiday apartment Appartamento in Palazzo Bucelli with step-free access and interior in Montepulciano is the perfect ...
From $262 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Apartment 'Aurora' with Private Terrace, Wi-Fi and Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The holiday apartment Casa di Aurora is located in Montepulciano and is the ideal accommodation for a relaxing getaway. ...
From $139 per night (USD)VRBO
- From $845 per night (USD)
Expedia
TERRACQUA--an oasis of peace in the Tuscan hills
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 18
Bed & breakfast in Chiusi with a hot tub A hot tub and laundry facilities are available at this smoke-free bed & breakfa ...
From $845 per night (USD)Expedia
- From $143 per night (USD)
VRBO
Apartment 'Villa Rosa' with Mountain View and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The holiday apartment Podere Villa Rosa, which is situated in Torrita di Siena, overlooks the nearby mountain. The 90 m² ...
From $143 per night (USD)VRBO
- From $366 per night (USD)
VRBO
Homerez - Enchanting House in Trequanda + Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our charming holiday home in Trequanda, perfect for a relaxing getaway with family or friends. Here, you can ...
From $366 per night (USD)VRBO
- From $173 per night (USD)
VRBO
Homerez - Apartment in Trequanda with pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover a charming holiday rental with fantastic views of the garden and mountains. Perfect for couples, this studio of ...
From $173 per night (USD)VRBO
- From $586 per night (USD)
Expedia
Villa Montisi by Interhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Montisi 15 km from Montalcino: Modern, beautiful house "Villa Montisi", 2 storeys, built in 2020, surrounded by trees an ...
From $586 per night (USD)Expedia
- From $176 per night (USD)
VRBO
Charming Ground-Floor Apartment just steps from Montepulciano's Historic Center
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to horse riding, winery tours, and more, this smoke-free vacation home brings it all within reach. There's conv ...
From $176 per night (USD)VRBO
- From $191 per night (USD)
VRBO
Holiday apartment Abbadia for 1 - 2 persons with 1 bedroom - Holiday apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ED Refnr. 3189869 The Elefantino flat is our smallest apartment. It owes its name to the elephant in the original coat ...
From $191 per night (USD)VRBO
- From $1019 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
Dolce Pienza - Modern Home in the Historic Center
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
<p>Nestled in Pienza, this 2-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and the outdo ...
Click For PricingExpedia
- From $178 per night (USD)
VRBO
Samsara Apartment elegant apartment in the historical center.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Discover the magic of this elegant, fully renovated accommodation. You'll find a serene environment, with minimalist fur ...
From $178 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
The holiday apartment Piccolo Rustico is located in Scrofiano and offers a wonderful view of the mountains. The 50 m² pr ...
From $207 per night (USD)Expedia
- From $676 per night (USD)
VRBO
Beautiful private villa for 6 guests with private pool, WIFI, A/C, TV and patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Property Summary The modern and beautiful two-story Villa Montisi, built in 2020, is surrounded by trees and fields in M ...
From $676 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Apartment 'Comfort Alle Terme' with Balcony and Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Chianciano Terme, this 110 m² apartment can accommodate up to 5 people and features 2 bedrooms, a living room ...
From $338 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Poggio del Raglio: Relax&Nature
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
<p>Located in Trequanda, this welcoming vacation home brings it all within your reach. Thanks to the convenient onsite p ...
From $294 per night (USD)VRBO
- From $511 per night (USD)
VRBO
Vacation home for 6 guests with 90m² in Cortona (295159)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p>Located in Cortona, this welcoming vacation home brings it all within your reach. Val di Chiana is an easy 13-minute ...
From $511 per night (USD)VRBO
- From $903 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
Villa Vesta by My Villa Collection
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
Just 2 km from the medieval village of San Casciano dei Bagni and the renowned Fonteverde spa, Villa Vesta is an exclusi ...
Click For PricingExpedia
- From $140 per night (USD)
VRBO
Boutique Apartment Natura
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Elegant in shades of Sage Green and Brilliant, newly renovated apartment on the first floor of 60 square meters, has Tr ...
From $140 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Premium Apartment - Helichrysum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Featuring a private entrance, this air-conditioned apartment comprises 1 living room, 2 separate bedrooms and 2 bathroom ...
From $399 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Apartment 'Di Sopra' with Shared Pool, Shared Terrace and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Casina di Sopra apartment in Sinalunga offers 45 sqm of comfortable space for up to three guests. It features one be ...
From $146 per night (USD)VRBO
- From $153 per night (USD)
Expedia
Apartment 'Di Sotto' with Shared Pool, Shared Terrace and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Apartment Casina di Sotto in Sinalunga offers 45 sqm of space for up to 2 guests. You have 1 bedroom with king-sized bed ...
From $153 per night (USD)Expedia
- From $110 per night (USD)
VRBO
Room 'Queen' with Balcony, Wi-Fi and Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Room Queen Room in Bettolle offers 25 sqm of space for up to 2 guests with 1 bedroom and 1 bathroom. You have a comforta ...
From $110 per night (USD)VRBO
- From $151 per night (USD)
Expedia
Room 'Family Suite' with Shared Pool, Terrace and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Room Family Suite in Sinalunga offers 45 sqm of space for up to 4 guests. You have 1 bedroom and 1 bathroom during your ...
From $151 per night (USD)Expedia
- From $117 per night (USD)
VRBO
Beautiful apartment for 3 people with A/C, WIFI, patio and pets allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Property Summary Le rondini is a modern and comfortable 2-family house in Montepulciano, Italy. It features two apartmen ...
From $117 per night (USD)VRBO
- From $1013 per night (USD)
Expedia
Spacious Holiday Home in Radicofani
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 20
Imagine a serene escape nestled in the beautiful countryside of Radicofani, where a spacious holiday home awaits you wit ...
From $1013 per night (USD)Expedia
- From $128 per night (USD)
VRBO
Villa 'Anni '50' with Private Garden and Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Sarteano, Tuscany, this finely renovated 1950s villa covers 100 sqm and can accommodate up to 8 guests. It of ...
From $128 per night (USD)VRBO
- From $128 per night (USD)
Expedia
Apartment 'Isidora' with Private Garden, Wi-Fi and Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Acquaviva, Casa Isidora offers a comfortable 60 sqm apartment that accommodates up to 4 guests. You will find ...
From $128 per night (USD)Expedia
- From $118 per night (USD)
VRBO
Bellarmino Boutique Apartments
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>While you're here, you can enjoy all the comforts of home and more, including a rainfall showerhead and free WiFi, as ...
From $118 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Panorama House - Two Bedroom Apartment, Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
“Panorama House” is a bright and spacious apartment located in Sinalunga, ideal for those who want to explore the wonder ...
From $184 per night (USD)Expedia
- From $1703 per night (USD)
VRBO
Borgo Belsedere -Perfect for Family-Reunions, Retreats, intimate Weddings & more
- Bedrooms:
- 9
- Bathrooms:
- 11
- Sleeps:
- 22
Within a 300-hectare organic estate of vineyards, olive groves and truffle fields, Borgo Belsedere covers an area of mor ...
From $1703 per night (USD)VRBO
- From $104 per night (USD)
Expedia
Oliveto Del Cantarello
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy detached house, free on three sides, featuring an outdoor space furnished with table and chairs, ideal for lunches ...
From $104 per night (USD)Expedia
- From $309 per night (USD)
VRBO
Maria Gabriella Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
In the heart of the enchanting village of Monticchiello, this property offers two independent accommodations: a house an ...
From $309 per night (USD)VRBO
- From $154 per night (USD)
Expedia
Maria Gabriella Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the heart of the enchanting village of Monticchiello, this property offers two independent accommodations: a house an ...
From $154 per night (USD)Expedia
- From $411 per night (USD)
VRBO
Maria Gabriella Holiday Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Independent House with Cottage in Monticchiello In the heart of the charming village of Monticchiello, this independent ...
From $411 per night (USD)VRBO
- From $310 per night (USD)
Expedia
Cozy house in Val d'Orcia with breathtaking views and unforgettable sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
<p>Close to wildlife walks, cycling, and more, this pet-friendly vacation home brings it all within reach. Thanks to the ...
From $310 per night (USD)Expedia
- From $176 per night (USD)
VRBO
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)VRBO
- From $351 per night (USD)
Expedia
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)Expedia
- From $469 per night (USD)
VRBO
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)VRBO
- From $117 per night (USD)
Expedia
Beautiful villa for 4 people with WIFI and TV, close to Montepulciano
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Oliveto Del Cantarello is a beautiful vacation rental (76 sq m) with WiFi internet. The property can sleep up to four p ...
From $117 per night (USD)Expedia
- From $1040 per night (USD)
VRBO
Podere Gellino 14, Emma Villas
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
The rate includes: - Utilities: electricity/heating, water, gas for kitchen use - weekly linen, initial and final cleani ...
From $1040 per night (USD)VRBO

























































