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Compare 940 Villas in Castiglione d'Orcia with updated reviews, rates, and availability.

Tuscan stone villa with private pool surrounded by greenery
Pool
Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (88)
"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
Stunning private villa for 4 guests with WIFI, pool, A/C, TV, terrace and parking
Pool
Stunning private villa for 4 guests with WIFI, pool, 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...
Stunning private villa for 4 guests with WIFI, pool, A/C, TV, terrace and parking
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Pool
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
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Exterior
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
exclusive, luxurious Farmhouse, between Rome and Florence, garden, heated pool
Exterior
exclusive, luxurious Farmhouse, between Rome and Florence, garden, heated pool
9.8 out of 10, Exceptional, (8)
"From the breathtaking views to the comfortable beds, soft linens and beautiful antiques — this villa was a charming location for a most relaxing week in the Umbrian hills! Made all the more fantastic by Stephanie, who at the drop of a hat helped arrange some incredible experiences for our family! "
exclusive, luxurious Farmhouse, between Rome and Florence, garden, heated pool
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Outdoor pool
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
10.0 out of 10, Exceptional, (44)
"The house, setting and host Luigi will guarantee an exceptional stay in this beautiful setting overlooking the Tuscan Hills. We spent a week here and absolutely loved the classic Tuscan decor, roomy interior, wonderful kitchen,outdoor seating and pool. Property is meticulously maintained with unmatched views of the hills. Bedrooms are roomy, beds very comfortable, and all with en suite bathrooms. If you like peace and quiet in a country setting the villa is for you. Every positive experience...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Villa Podere Belvedere
Bathtub, hair dryer, towels
Villa Podere Belvedere
9.8 out of 10, Exceptional, (11)
"Our stay at Villa Podere Belvedere was just wonderful. Our family had the most relaxing time at the Villa, enjoying morning walks in the picturesque country side, lovely lunches by the pool and driving to the many charming Towns in the area all contributed to a wonderful stay. My only negative comment is that it would have been helpful if we had been informed that absolutely no household cleaning products or catering supplies would be provided, we could have brought these items with us. Given...
Villa Podere Belvedere
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia Sleeps 15.
Outdoor pool
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia Sleeps 15.
10.0 out of 10, Exceptional, (6)
"This historic Tuscan farmhouse has been renovated to capitalize on spaciousness, multiple bedrooms with private baths, and a truly unique old European feel. Situated in a valley surrounded by beautiful fields and hillside villages, every night offered beautiful sunsets only to be eclipsed by amazing sunrises. Our caring, friendly host immediately made us feel welcomed and was eager to accommodate any needs that our group might have. Our family was very comfortable, taking day trips to nearby...
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia Sleeps 15.
Beautifully restored Tuscan villa, with private pool and breathtaking views
Property grounds
Beautifully restored Tuscan villa, with private pool and breathtaking views
10.0 out of 10, Exceptional, (14)
"Podere Macchione was the perfect place for our family gathering in Tuscany. Cally was an absolutely incredible host who looked after every detail, and whose home was a little bit of heaven on earth for us to enjoy. Everything, from the “out of this world” views, to the beautiful interior design, to wine tasting with Emily, and to a classic Tuscan dinner with Massi, was perfect. We will cherish this vacation, and have, in large part, Cally to thank for it!!!"
Beautifully restored Tuscan villa, with private pool and breathtaking views
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Exterior
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
9.4 out of 10, Exceptional, (40)
"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
View from property
Villa Piandisette - Four Bedroom Villa, Sleeps 10
9.0 out of 10, Wonderful, (7)
"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
Design villa with large swimming pool in the heart of the Tuscan countryside
Outdoor pool
Design villa with large swimming pool in the heart of the Tuscan countryside
Design villa with large swimming pool in the heart of the Tuscan countryside
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Property grounds
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 ￥37,844
￥46,862 total
includes taxes & fees
Oct 24 - Oct 25
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Terrace/patio
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
8.0 out of 10, Very Good, (2)
"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 WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Pool
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, parking, close to Montalcino
Villa Lauretana
Front of property
Villa Lauretana
Villa Lauretana
Stunning private villa with WIFI, private pool, TV, panoramic view, parking, close to Montepulciano
Pool
Stunning private villa with WIFI, private pool, TV, panoramic view, parking, close to Montepulciano
10.0 out of 10, Exceptional, (51)
Stunning private villa with WIFI, private pool, TV, panoramic view, parking, close to Montepulciano
Big house
Pool
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
Pool
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
Pool
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
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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
Property grounds
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
Pool
Villa Campiglia - Holiday Country Villa with swimming pool in Orcia Valley, Tuscany
10.0 out of 10, Exceptional, (30)
"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
Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (34)
"This property is just outside the town gates, making it easy to walk to town for dining options. Their restaurant is a good choice too. Within easy driving distance are great photo op places, as well as a couple of towns worth visiting. From the back of the property you can also take a couple of iconic Tuscany photos."
The price is ￥25,073
￥28,064 total
includes taxes & fees
Oct 3 - Oct 4
Casanova - Panoramic Rooms and Suites
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.