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Our top choices for San Rocco a Pilli vacation homes

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola

Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View
Boccheggiano
9.6 out of 10, Exceptional, (56)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
United Kingdom
Patrick H.
The price is AED 12,472
AED 14,812 total
includes taxes & fees
31 Dec - 1 January 2026
Private House with Exclusive Swimming Pool Heated and Amazing View

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveler
The price is AED 340
AED 488 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Comfort, relaxation and nature

Comfort, relaxation and nature
Monticiano
10.0 out of 10, Exceptional, (1)
"Appartamento perfetto non manca nulla e proprietari accoglienti, e gentilissimi. Da tornare"
Italy
Sandra V.
The price is AED 310
AED 439 total
includes taxes & fees
22 Dec - 23 Dec
Comfort, relaxation and nature

House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
9.4 out of 10, Exceptional, (3)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is AED 602
AED 1,174 total
includes taxes & fees
2 Jan - 3 January 2026
House with pool for 4 pax

Exclusive Stone Tower.

Exclusive Stone Tower.
Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
The price is AED 364
AED 622 total
includes taxes & fees
4 Jan - 5 January 2026
Exclusive Stone Tower.

LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST
Toscana
The price is AED 228
AED 559 total
includes taxes & fees
22 Dec - 23 Dec
LOVE NEST SIENA YOUR LOVE NEST

Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Rosmarino
Montalcino
9.0 out of 10, Wonderful, (4)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
The price is AED 516
AED 602 total
includes taxes & fees
22 Dec - 23 Dec
Podere Belsogno-camera Rosmarino

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is AED 516
AED 602 total
includes taxes & fees
22 Dec - 23 Dec
Podere Belsogno-camera Lavanda

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is AED 551
AED 559 total
includes taxes & fees
8 Jan - 9 January 2026
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Detached house with garden a few minutes from the abbey of San Galgano

Detached house with garden a few minutes from the abbey of San Galgano
Toscana
The price is AED 215
AED 520 total
includes taxes & fees
22 Dec - 23 Dec
Detached house with garden a few minutes from the abbey of San Galgano

Domotic Suite at Villa Anna

Domotic Suite at Villa Anna
Buonconvento
The price is AED 310
AED 578 total
includes taxes & fees
27 Dec - 28 Dec
Domotic Suite at Villa Anna

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (2)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is AED 2,146
AED 3,789 total
includes taxes & fees
3 Jan - 4 January 2026
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is AED 1,731
AED 2,106 total
includes taxes & fees
7 Jan - 8 January 2026
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is AED 645
AED 1,471 total
includes taxes & fees
22 Dec - 23 Dec
Agritourism in val d'orcia

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 774
AED 1,114 total
includes taxes & fees
22 Dec - 23 Dec
Charming Siena Countryside Stay

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Monteriggioni
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is AED 1,041
AED 1,480 total
includes taxes & fees
22 Dec - 23 Dec
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Podere Belsogno

Podere Belsogno
Montalcino
10.0 out of 10, Exceptional, (1)
"Charming and attentive hosts, stunning terrace with amazing views and a modern, attractive and well equipped rental that was a short walk to downtown Montalcino. We had a fabulous time and would go back again."
Canada
David P.
The price is AED 1,505
AED 1,725 total
includes taxes & fees
22 Dec - 23 Dec
Podere Belsogno

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
MONTERIGGIONI
10.0 out of 10, Exceptional, (1)
"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "
United States
Anonymous traveler
The price is AED 1,157
AED 1,836 total
includes taxes & fees
22 Dec - 23 Dec
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

Chateau / Country House

Chateau / Country House
Sovicille
The price is AED 258
AED 400 total
includes taxes & fees
28 Dec - 29 Dec
Chateau / Country House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top San Rocco a Pilli Hotel Reviews