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Our top choices for Pentolina vacation homes

Vacation Home in Monticiano

Comfort, relaxation and nature
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 308
AED 436 total
includes taxes & fees
12 Dec - 13 Dec
Comfort, relaxation and nature
10.0 out of 10, Exceptional, (1)
"Très bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is AED 555
AED 696 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Tuscan-style apartment Suitable for families. Pets allowed
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 12,385
AED 14,631 total
includes taxes & fees
31 Dec - 1 January 2026
Private House with Exclusive Swimming Pool Heated and Amazing View

Vacation Home in Toscana

LOVE NEST SIENA YOUR LOVE NEST
The price is AED 252
AED 581 total
includes taxes & fees
13 Dec - 14 Dec
LOVE NEST SIENA YOUR LOVE NEST

Vacation Home in Casole d'Elsa

House with pool for 4 pax
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 598
AED 1,179 total
includes taxes & fees
5 Jan - 6 January 2026
House with pool for 4 pax

Vacation Home in Montalcino

Podere Belsogno-camera Lavanda
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 512
AED 598 total
includes taxes & fees
12 Dec - 13 Dec
Podere Belsogno-camera Lavanda

Vacation Home in Casciano

Exclusive Stone Tower.
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 380
AED 636 total
includes taxes & fees
5 Jan - 6 January 2026
Exclusive Stone Tower.

Vacation Home in Montalcino

Podere Belsogno-camera Rosmarino
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 512
AED 598 total
includes taxes & fees
11 Dec - 12 Dec
Podere Belsogno-camera Rosmarino
The price is AED 214
AED 517 total
includes taxes & fees
11 Dec - 12 Dec
Detached house with garden a few minutes from the abbey of San Galgano
The price is AED 547
AED 555 total
includes taxes & fees
8 Jan - 9 January 2026
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Vacation Home in Buonconvento

Domotic Suite at Villa Anna
The price is AED 307
AED 574 total
includes taxes & fees
17 Dec - 18 Dec
Domotic Suite at Villa Anna
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 1,034
AED 1,470 total
includes taxes & fees
15 Dec - 16 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.

Vacation Home in Sovicille

Chateau / Country House
The price is AED 256
AED 397 total
includes taxes & fees
28 Dec - 29 Dec
Chateau / Country House
The price is AED 683
AED 811 total
includes taxes & fees
14 Dec - 15 Dec
Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
The price is AED 888
AED 888 total
includes taxes & fees
15 Dec - 16 Dec
Casale Torricella: Relax Among Woods with Sea View
The price is AED 1,771
AED 2,247 total
includes taxes & fees
14 Dec - 15 Dec
Vacation Home "Casalino" with Shared Pool, Shared Garden & Wi-Fi

Vacation Home in Montalcino

Podere Belsogno
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 1,495
AED 1,713 total
includes taxes & fees
11 Dec - 12 Dec
Podere Belsogno
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 2,131
AED 3,758 total
includes taxes & fees
3 Jan - 4 January 2026
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
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 1,149
AED 1,819 total
includes taxes & fees
11 Dec - 12 Dec
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
10.0 out of 10, Exceptional, (1)
"We had the best time in this beautiful place! The location is absolutely stunning — the garden, house, pool, and everything was perfect and very clean. Tamara is super friendly and kind; she even brought us fresh bread every morning and sold us her delicious honey! Her two dogs are also very sweet and added to the warm, welcoming vibe of the place. The space is very spacious and a truly beautiful corner of nature that you must see.Thank you again, Tamara, for everything!"
Germany
Lea B.
The price is AED 2,812
AED 3,333 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Home 'Podere Le Rote' with Private Pool, Private Garden and Wi-Fi
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 Pentolina Hotel Reviews