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Compare 1012 Villas in Castiglione d'Orcia with updated reviews, rates, and availability.

Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (89)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
10.0 out of 10, Exceptional, (45)
"Luigi went above and beyond in providing suggestions of restaurants and things to do in the area. He was also helpful when we were have trouble calling our car rental….always willing to help out and answer questions. The home is very clean and has the old Italian rustic charm. The beds were comfortable. There is no AC but fans are provided for every room. There were beautiful sunsets every night by the pool. The views of the rolling Tuscan hills were spectacular. The color and intensity of the...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
10.0 out of 10, Exceptional, (7)
"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Beautiful private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Beautiful private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (45)
"It's hard to imagine what could have been better. The villa is stunning. On a hilltop will amazing views. Well appointed and with 12 rooms, all with ensuites. A large kitchen and dining space and loads more outside space than the pictures really show. Morning coffee on the lower sun terrace, the afternoon spent by the pool, the evening in the jacuzzi, and then wine (SO MUCH WINE) from the provided supplies to talk as the night grew around us. Not to mention the small gym, or table...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
9.6 out of 10, Exceptional, (37)
"Our family had a fantastic time in this rural villa. The space was very clean and well-kept as were the grounds (almost too much as they were there mowing grass several times during our stay and for most of the day). The surroundings were very peaceful and quiet and the countryside views were breathtaking with many outdoor areas on the property to enjoy - perfect for meals al fresco! Property is wonderfully located and ideal for day trips in Tuscany/Umbria from this home base but made sure we...
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Tuscan villa pool spa Siena, Montepulciano Montalcino Pienza Florence
10.0 out of 10, Exceptional, (104)
"We really enjoyed our stay. We loved the small town feel and the welcome that Valerio gave us. We wish the weather could have been better so that we could’ve enjoyed the views more, but still an excellent time. We especially enjoyed cooking a meal in the kitchen together using ingredients we found at the local vendors in cetona! We hope to be back soon!"
Tuscan villa pool spa Siena, Montepulciano Montalcino Pienza Florence
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
9.4 out of 10, Exceptional, (41)
"Our group of five women thoroughly enjoyed our two-week stay at Miralaghi. We were in the main house (old hunting lodge) with 4-bedrooms, 3 baths, huge living space, kitchen, carport, and private pool. Miralaghi is a unique property, located between Paciano and Moiano, high up on a hillside. It is very peaceful, quiet and provides lovely hiking trails on the huge, 750 acre property. It's a perfect retreat at the end of a day of visiting nearby hill towns. Our host, Mausi, was a delight and so...
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Villa Piandisette - Four Bedroom Villa, Sleeps 10
9.0 out of 10, Wonderful, (8)
"I really liked the villa. The rooms were ready, the beds were made. The owner welcomed us very kindly, showed us all the rooms and the pool. We were on vacation for 8 days and we really liked it, but there were a few details that spoiled our vacation a little or maybe not a little: The villa is suitable for a large number of people up to 10, but it is not very suitable for a longer stay, as I think longer than 3-4 days, because for a longer stay you want the first floor, which is the main one...
Villa Piandisette - Four Bedroom Villa, Sleeps 10
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
10.0 out of 10, Exceptional, (2)
"Such a quaint home, clean, quiet and beautiful. Close to the center of the very small town of Montepulciano. The host is very sweet and even cooked a cake to welcome us to their home. The view of the valley from the home is simply breathtaking."
The price is SAR 1,769
SAR 2,111 total
includes taxes & fees
23 Dec - 24 Dec
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
8.8 out of 10, Excellent, (3)
"This house is very nice. It is centrally located outside Siena and good location to explore all over Tuscany. It is off the beaten path so you’ll definitely need a rental car. Even just to get there. It is remote. Which is a plus but also has some drawbacks. We went in March so pool was closed. Too cold to swim. House is several levels. Kitchen and dining room are downstairs. We cooked several simple meals after going into town to grab groceries. Nearby town is nice. Not a lot of restaurant...
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Big house
7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (100)
"A wonderful setting, terrific location and ideal large house for our 3 generation group of extended family members. The 8 children under 11ys had a fantastic time playing with their cousins enjoying the grounds, pool area, tennis court and football goalposts. Sonja was a great host - relaxed but responsive and a thoughtful cook for the two prepared meals she made for us"
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (55)
"Lovely villa, great host. We really enjoyed our stay. "
A private luxury retreat in Montalcino
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is SAR 578
SAR 660 total
includes taxes & fees
23 Nov - 24 Nov
Il Poggio dell'Eremita
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
10.0 out of 10, Exceptional, (195)
"In summary, a brilliant villa, perfect for our large group of families (4 couples with multiple kids). Citta della Pieve is a lovely town and there are loads of places to.visit nearby. We had a great time abd the hosts were very helpful. Would highly recommend."
PRIVATE VILLA WALKING DISTANCE, PRIVATE POOL AND JACUZZI
Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (78)
"We absolutely loved our stay at this villa! It was just wonderful, and Luigi was a fantastic host! The views from every part of the villa are amazing! It was so fun to see all of the sheep each morning and watch the sunset in the evenings. We were fortunate enough to be in town for the olive festival in Montisi, the quaint little village just a few miles away. We had a blast! The recommended chef who cooked for us at the villa, Giancarlo from the Tuscan Chef, was incredible! What a fantastic...
Villa in Montalcino, exclusive for you, stunning view!!!
Villa with private pool, air conditioning near wineries at 3km from village
9.4 out of 10, Exceptional, (40)
"Great time with friends! Can't beat the location and the hosts were amazing and responsive."
Villa with private pool, air conditioning near wineries at 3km from 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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Other property types in Castiglione d'Orcia

Old Tuscan house in the medieval village of Castiglione d'Orcia
9.6 out of 10, Exceptional, (15)
"Lovely spot to be in the middle of this lovely village."
Old Tuscan house in the medieval village of Castiglione d'Orcia
Villa Campiglia - Holiday Country Villa with swimming pool in Orcia Valley, Tuscany
10.0 out of 10, Exceptional, (29)
"Avons passé une semaine de reve. Jolie maison agréable et pratique, nous étions 8 PERSONNES, chacun à pu avoir son intimité. Avons apprécié la magnifique vue sur le sud Toscane, le calme,..... Envie d'y retourner."
Villa Campiglia - Holiday Country Villa with swimming pool in Orcia Valley, Tuscany
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (104)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 553
SAR 608 total
includes taxes & fees
28 Nov - 29 Nov
Hotel San Gregorio
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.