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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 695 Villas in San Rocco a Pilli with updated reviews, rates, and availability.

Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Villa Simo, absolute tranquility

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (67)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Pool

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
Il Boschetto an oasis of peace and nature in Siena
Exterior

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (31)
"The location was excellent, 30 minute walk (2.1 km) to the main gate of Siena or 15 minute bus ride (bus stop 25 meters from the house). The home is beautiful, lots of amenities, it was very rustic. The pool area could use a good trimming, the online photos showed the property better than it actually was but not too far off."
Il Boschetto an oasis of peace and nature in Siena
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Exterior

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (95)
"Our host was responsive to our questions and needs. He also arranged a women to come to the property and prepare dinner for us on two separate nights.To our host, thank you."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Sunset from our garden

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (87)
"I wish we could have stayed longer; such a beautiful location. The villa was very nice and comfortable. We enjoyed meals prepared by Serena twice during our visit; she cooked multi-course dinners that were delicious. Highly recommend the property and Serena’s cooking. We look forward to going back!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa seen from the pool

FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

10.0 out of 10, Exceptional, (56)
"Stay was excellent, a great house. Owners were super helpful. A property with over 100 olive trees. If I return this is where I will be 😎"
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Villa with private pool and panoramic view in beautiful Val d'Orcia
Pool

Villa with private pool and panoramic view in beautiful Val d'Orcia

10.0 out of 10, Exceptional, (5)
"We had stayed at this property for years before Jennifer purchased it. And do hope to continue. We appreciate the effort and care to details she put into updating it and providing an excellent experience. This property is well located to see numerous villages in the area."
Villa with private pool and panoramic view in beautiful Val d'Orcia
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

Wonderful private villa for 4 people 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...
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Villa in Montalcino, exclusive for you, stunning view!!!
Exterior

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 "Le Vallecchie" overlooking Siena and with private swimming pool
Pool

Villa "Le Vallecchie" overlooking Siena and with private swimming pool

9.6 out of 10, Exceptional, (29)
"Lovely rustic property in scenic location, large garden grounds and decent swimming pool. Property worked well for our family of 7 adults ranging three generations."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
View of the Villa from garden-pool

Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly

9.6 out of 10, Exceptional, (53)
"The property was beautiful and very safe. The pool was fabulous , the scenery breath taking and the hosts very friendly and welcoming people. Close to hiking trails with a pizzeria close by . A car is recommended with parking in a gated property . "
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Villa Larniano, With Private Pool And View On Vineyard
Pool

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (64)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Our Anglican Church friends (three couples) from Texas began our Italy tour in Rome and then continued to Florence for a few days. We spent our final four days at the beautiful Villa Santa Chiara, a short walk from the gates of downtown Siena, Italy. This wonderful villa could accommodate more people than our group of six, but it was an excellent choice for our three couples. Each couple had their own private apartment with a bathroom, kitchen, and spacious living area. The villa was...
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Villa with private swimming pool in quiet area, private garden, panoramic views
Pool

Villa with private swimming pool in quiet area, private garden, panoramic views

10.0 out of 10, Exceptional, (8)
"La maison est très calme, très propre et bien équipée, accessible en partie par un chemin de terre depuis le joli village de Radicondoli, . La vue sur les collines avoisinantes est très agréable, en particulier de la piscine (hors-sol). Il faut compter environ 45 minutes de jolies routes pour se rendre à Sienne, Volterra ou San Giminiano. Beaucoup d'animaux sauvages dans la nature, si vous êtes chanceux comme nous... Sarka est une hôtesse sympathique et attentionnée. Avec son mari, elle produit...
Villa with private swimming pool in quiet area, private garden, panoramic views
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
The property has a private road and gate

Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi

9.8 out of 10, Exceptional, (9)
"The villa is beautiful, spacious, clean and comfortable. The location is excellent. There are horses and ponies on the grounds. The best part is the hostess and the host. They are so accomadating and kind. The pasta we dinner and pizza party were great! "
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Wonderful private villa with private pool, WIFI, TV, patio, panoramic view, parking, close to Siena
Building Exterior, Pool

Wonderful private villa with private pool, WIFI, TV, patio, panoramic view, parking, close to Siena

10.0 out of 10, Exceptional, (15)
Wonderful private villa with private pool, WIFI, TV, patio, panoramic view, parking, close to Siena
Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Outdoor

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
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Pool

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
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Exterior

Torretta Barbischio, Gaiole in Chianti, Siena and Chianti

10.0 out of 10, Exceptional, (4)
"This property is beautiful inside and out. If I remember correctly, there’s 20-25 people currently living in Barbischio. It’s peaceful with fantastic views to the west over Gaiole. Gailoe is less than 10 minutes away with access to grocery, meat market, several restaurants and gelato! The location is perfect with access to the train in Montivarchi in 25-30 minutes. Radda, Volpaia, Greve,,Siena, San Gimignano…all close. We will stay here again. "
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Macia Viva, Castellina in Chianti, Siena and Chianti
Pool

Macia Viva, Castellina in Chianti, Siena and Chianti

8.0 out of 10, Very Good, (2)
"The views were beyond compare! Proximity to Castellina in Chianti was wonderful and the management team were responsive to a few issues. My main comment would be, especially considering the rental cost, that the furniture and kitchen supplies (dishes etc) needs upgrading and the quality of the beds/linens should be improved. Overall however, it was a lovely stay! Grazie."
Macia Viva, Castellina in Chianti, Siena and Chianti
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 San Rocco a Pilli

Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (150)
"Wonderful location!!! Everything within walking distance. Friendly staff, clean modern room. Shower needs repairing. Will definitely return to stay here. If you are driving to the hotel, It’s a ZTL zone so contact the hotel to make arrangements for your car to be garaged. Don’t need a car here. It is in the best location!!!"
The price is AED 527
AED 595 total
includes taxes & fees
17 Feb - 18 Feb
Il Battistero Siena - Residenza d'Epoca
villa con vista panoramica
Pool

villa con vista panoramica

9.0 out of 10, Wonderful, (2)
"Die Wohnung liegt ruhig im schönen Dorf Chiusdino, das Meer ist ca. 1 Stunde entfernt, aber der Pool eignet sich gut zum Baden. Es ist genug Platz für 4 Personen. Der Vermiter Paolo ist sehr freundlich und hilfsbereit, die Kommunikation war super. Uns hat es sehr gut gefallen und wir kommen gerne wieder!"
villa con vista panoramica
ApartHotel Anghel
Room

ApartHotel Anghel

8.2 out of 10, Very Good, (311)
"Nice place, quiet and clean!"
The price is AED 285
AED 329 total
includes taxes & fees
20 Feb - 21 Feb
ApartHotel Anghel
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.

Frequently asked questions

How much do villas in San Rocco a Pilli cost?
Prices for villas in San Rocco a Pilli range between and per night. Whatever your budget, you’re sure to find something that fits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in San Rocco a Pilli?
Use up your vacation days and choose from 695 villas in San Rocco a Pilli. For a family vacation, a getaway with your besties or anything in between, Expedia can help you find the perfect place in a few simple clicks.
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