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Our top choices for Pentolina vacation homes

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

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

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 383
AED 645 total
includes taxes & fees
4 Jan - 5 January 2026
Exclusive Stone Tower.

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

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

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-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

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

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

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

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

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

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

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

THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.0 out of 10, Very Good, (4)
"Excellent location, very nice apartment was just like the pictures. Painless check-in, we had a comfortable wonderful 3 days in Siena. The only negative was the drain in the master shower backs up, but there's a second bathroom so we just showered in there. Great place!"
United States
Serena F.
The price is AED 362
AED 631 total
includes taxes & fees
22 Dec - 23 Dec
THE TOLOMEI - apartment in the heart of the main street

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

Holiday Home 'Podere Le Rote' with Private Pool, Private Garden and Wi-Fi

Holiday Home 'Podere Le Rote' with Private Pool, Private Garden and Wi-Fi
Castelnuovo di Val di Cecina
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 2,832
AED 3,357 total
includes taxes & fees
4 Jan - 5 January 2026
Holiday Home 'Podere Le Rote' with Private Pool, Private Garden and Wi-Fi

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

Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi
Roccastrada
The price is AED 1,416
AED 1,574 total
includes taxes & fees
6 Jan - 7 January 2026
Holiday Home 'Querciagrossa Da Dora' with Private Pool, Private Terrace and Wi-Fi

Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village

Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
Località Gerfalco Montieri
The price is AED 688
AED 817 total
includes taxes & fees
23 Dec - 24 Dec
Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
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