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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 902 Villas in San Rocco a Pilli with updated reviews, rates, and availability.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Property grounds

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

10.0 out of 10, Exceptional, (47)
"Nice house with a beautiful pool , well located to visit Tuscany. "
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (84)
"We had a wonderful stay, the location was perfect for a short 15 minute walk into Montisi. The countryside setting was lovely and peaceful. We enjoyed being surrounded by beautiful nature, watching the deer every evening was delightful. We hope to return in the future. "
Hilltop house in the heart of Tuscany with private pool
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Terrace/patio

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (108)
"We had a great stay in this home enjoying the views of the Tuscan country side. It is located close to Siena and is a perfect place to stay to make day trips to many towns and villages in Tuscany. Francesca was very attentive and helpful in explaining everything about the house and property. We would definitely stay again if ever in the area. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Outdoor pool, sun loungers

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

9.6 out of 10, Exceptional, (30)
"Really enjoyed our stay. A great place to relax."
Villa "Le Vallecchie" overlooking Siena and with private swimming pool
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Smart TV, fireplace, DVD player, stereo

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

10.0 out of 10, Exceptional, (51)
"We really appreciate the place and the quieteness of the house. The house is very beautiful and well equipped. We have spent a great week in Torre di Pancole. "
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Villa Costa, Stunning Villa in the heart of Tuscany.
Exterior

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (33)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Outdoor pool, a heated pool

Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake

10.0 out of 10, Exceptional, (45)
"AGRICOLA NECI is a luxury experience all the way. From the owner Patrick to the staff (Eva, Santiago and Gregorio) everyone was there to make sure our experience was memorable. The views of the surrounding valleys are incredible. The house itself is out of a movie. I highly recommend an extended vacation here."
Agricola Neci: Tuscan Rural Luxury with Housekeeping, Infinity Pool and a Lake
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Outdoor pool

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Terrace/patio

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.0 out of 10, Wonderful, (6)
"Only regret is that we couldn’t stay longer to explore more of Tuscany. Wish weather was a bit warmer to use the beautiful pool. Overall beautiful home with upscale features! We really enjoyed our stay!"
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Wonderful private villa for 4 guests with pool, A/C, WIFI, TV, terrace and parking
Pool

Wonderful private villa for 4 guests with pool, A/C, WIFI, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Wonderful private villa for 4 guests with pool, A/C, WIFI, TV, terrace and parking
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (21)
"We were a group of 4 families with toddlers and loved our stay at the villa! Alessandro was an excellent host and very responsive. The views and pool are stunning, and the house is clean and decently equipped. Highly recommended for a group stay in Chianti!"
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Outdoor 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
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (58)
"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
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Outdoor pool

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (53)
"Gabbianuzzo was so beautiful and secluded. We had a wonderful time exploring Tuscany from this villa. "
Quiet and Beautiful Property, Large Pool, Airco in bedrooms
Private villa in the heart of chianti with view of siena
Pool

Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena
Villa Casa al Sole Large Private Pool, WiFi
View from property

Villa Casa al Sole Large Private Pool, WiFi

9.8 out of 10, Exceptional, (20)
"Outstanding Villa. Vert comfortable and great location. Loved this place."
Villa Casa al Sole Large Private Pool, WiFi
Il Boschetto an oasis of peace and nature in Siena
Outdoor pool

Il Boschetto an oasis of peace and nature in Siena

9.8 out of 10, Exceptional, (33)
"The rooms are spacious and well equipped and the house can easily accommodate 10 people. The property is located in a wealthy enclave of Siena minutes from town yet it is completely private. The views are breathtaking and the property is gorgeous."
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
Outdoor pool

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

10.0 out of 10, Exceptional, (100)
"The whole family were together and enjoyed the beauty that surrounded us. It was a wonderful place that made for wonderful memories."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor dining

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Villa with unique view of Siena with private pool
Outdoor pool

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
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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Frequently asked questions

How much do villas in San Rocco a Pilli cost?
Villas in San Rocco a Pilli cost between and per night. These escapes give you the privacy to enjoy your own space at a price that’s easy on your wallet. 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?
Claim your vacation time and pick from 902 villas in San Rocco a Pilli. For a family vacation, a romantic break and everything in between, Expedia will help you find an ideal stay in a few simple clicks.
Why book your villa in San Rocco a Pilli with Expedia?
With Expedia, you’ll have no trouble finding your ideal villa in San Rocco a Pilli. Vacationing with the kids? Use our handy filters to search for stays with amenities like WiFi and a pool. If you have a budget in mind, decide on how much you’re willing to spend and your preferred star rating. We’ll help you find the perfect stay that suits your taste and style.