Villa Compare logo

Villas in Roccastrada, Tuscany

Discover the secrets of Tuscany's hidden gem, Roccastrada. From secluded countryside retreats to charming village getaways, find your perfect villa holiday in this Italian treasure.

Villas in Roccastrada

Casa Reasco 6, Roccastrada, Grosseto and Maremma
£183  night
6
3
5
Details View Offers
La Magia 8+2, Emma Villas
4.7/5
£436  night
10
4
5
Details View Offers
Tenuta Di Litiano With Pool, Roccastrada, Italy
£198  night
16
8
6
Details View Offers
Beautiful apartment in villa for 2 people with WIFI, TV, patio and parking
£56  night
2
1
1
Details View Offers
Villa Casale Villa Casale "Il Diaccio" with panoramic views of the Tuscan Maremma"Il DiaccioVilla Casale "Il Diaccio" with panoramic views of the Tuscan Maremma" with panoramic views of the Tuscan Maremma
5.0/5
£279  night
11
5
4
Details View Offers
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
£1152  night
5
2
1
Details View Offers
Stunning private villa with private pool, WIFI, TV, balcony, panoramic view and parking
£404  night
11
5
5
Details View Offers
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
£1043  night
4
2
1
Details View Offers
Villa Melissa - Stunning Tuscan Villa With Pool
£2125  night
14
7
6
Details View Offers
Lovely apartment in villa for 6 guests with WIFI, TV, terrace and parking
£108  night
6
3
2
Details View Offers
Casa Reasco 8, Roccastrada, Grosseto and Maremma
£213  night
8
4
5
Details View Offers
Beautiful private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and par...
£150  night
6
2
2
Details View Offers
Nice apartment in villa for 4 guests with WIFI, pool, TV, patio, pets allowed and parking
4.0/5
£91  night
4
2
1
Details View Offers
Casa Reasco 10, Roccastrada, Grosseto and Maremma
£233  night
10
5
6
Details View Offers
Casa Vecchia: Luxurious villa with shared pool, tennis court & stunning views!
£3581  night
9
3
3
Details View Offers
Casa Cinghiale: Luxurious villa with private pool, tennis court & stunning view!
5.0/5
£456  night
5
3
3
Details View Offers
Dream Pool, near Siena sea views, 9 people, romantically & culinary close
5.0/5
£309  night
9
4
3
Details View Offers
VILLA SAN GALGANO - Villa San Galgano
£420  night
8
3
3
Details View Offers
An old mill, completely renovated, in the middle of nature
4.7/5
£120  night
4
2
1
Details View Offers
Holiday home with exclusive swimming pool in the Tuscan Maremma
5.0/5
£251  night
6
3
3
Details View Offers

Why a holiday villa in Roccastrada

Roccastrada is a hidden gem nestled in the rolling hills of Tuscany, offering a tranquil and authentic Italian experience that's perfect for a relaxing villa holiday. The village itself is small and charming, with narrow streets lined with local shops, cafes, and restaurants serving up delicious traditional cuisine.

Staying in a villa in Roccastrada allows you to fully immerse yourself in the region's rich culture and history, from exploring medieval towns like Siena and San Gimignano to sampling some of the world's best wines and olive oils. With its picturesque countryside, charming villages, and stunning landscapes, Tuscany is the ultimate destination for nature lovers, foodies, and anyone seeking a relaxing getaway from the stresses of everyday life.

When to rent a villa in Roccastrada

Roccastrada, Italy is a wonderful destination for a villa holiday throughout the year, with each season offering its own unique charm and attractions. Spring (March to May) is a lovely time to visit, as the mild temperatures and blooming flowers create a picturesque landscape. The days are warm enough to enjoy outdoor activities like hiking and biking, while the evenings are still cool enough to relax in your villa's private garden or pool.

Summer (June to August) is peak tourist season in Roccastrada, with hot and sunny weather perfect for swimming, sunbathing, and exploring the surrounding countryside. If you're looking for a more relaxed atmosphere, consider visiting in autumn (September to November), when the crowds have dissipated and the temperatures are still warm but not as sweltering. Winter (December to February) is a great time to experience the authentic Italian Christmas celebrations, with festive markets and cozy villa getaways that will make you feel like you're part of the local community.

Where to go in Roccastrada

When it comes to choosing the perfect location for your villa holiday in Roccastrada, Italy, the options are endless. If you're looking for a secluded retreat with breathtaking views of the Tuscan countryside, consider staying in the hills surrounding Roccastrada village. Here, you can wake up each morning to stunning vistas and spend your days exploring the rolling hills, cypress-lined roads, and picturesque villages that dot the landscape.

Alternatively, if you prefer a villa location with easy access to local amenities, head to one of the charming hamlets that surround Roccastrada village. These small communities offer a range of shops, restaurants, and bars where you can sample local specialties like ribollita and pappardelle, as well as enjoy a glass of wine or two at one of the many enoteche (wine bars) in the area. Whether you're looking for relaxation or adventure, Roccastrada has something to offer every type of traveler.

Picture of two young girls swimming in a pool with their floatation rings
Family friendly villas
Find out more
Image of a woman swimming in a pool at a holiday home
Private pool villas
Find out more
Picture of a Titleist golf ball on the edge of the hole on a golfing green
Villas near golf course
Find out more

Villas in Roccastrada

Casa Reasco 6, Roccastrada, Grosseto and Maremma
£183  night
6
3
5
Details View Offers
La Magia 8+2, Emma Villas
4.7/5
£436  night
10
4
5
Details View Offers
Tenuta Di Litiano With Pool, Roccastrada, Italy
£198  night
16
8
6
Details View Offers
Beautiful apartment in villa for 2 people with WIFI, TV, patio and parking
£56  night
2
1
1
Details View Offers
Villa Casale Villa Casale "Il Diaccio" with panoramic views of the Tuscan Maremma"Il DiaccioVilla Casale "Il Diaccio" with panoramic views of the Tuscan Maremma" with panoramic views of the Tuscan Maremma
5.0/5
£279  night
11
5
4
Details View Offers
Pet-Friendly Finca Etrusco with Mountain View, Pool, Garden & Wi-Fi
£1152  night
5
2
1
Details View Offers
Stunning private villa with private pool, WIFI, TV, balcony, panoramic view and parking
£404  night
11
5
5
Details View Offers
Pet-Friendly Finca Lucente with Mountain View, Pool, Garden & Wi-Fi
£1043  night
4
2
1
Details View Offers
Villa Melissa - Stunning Tuscan Villa With Pool
£2125  night
14
7
6
Details View Offers
Lovely apartment in villa for 6 guests with WIFI, TV, terrace and parking
£108  night
6
3
2
Details View Offers
Casa Reasco 8, Roccastrada, Grosseto and Maremma
£213  night
8
4
5
Details View Offers
Beautiful private villa with WIFI, private pool, TV, patio, pets allowed, panoramic view and par...
£150  night
6
2
2
Details View Offers
Nice apartment in villa for 4 guests with WIFI, pool, TV, patio, pets allowed and parking
4.0/5
£91  night
4
2
1
Details View Offers
Casa Reasco 10, Roccastrada, Grosseto and Maremma
£233  night
10
5
6
Details View Offers
Casa Vecchia: Luxurious villa with shared pool, tennis court & stunning views!
£3581  night
9
3
3
Details View Offers
Casa Cinghiale: Luxurious villa with private pool, tennis court & stunning view!
5.0/5
£456  night
5
3
3
Details View Offers
Dream Pool, near Siena sea views, 9 people, romantically & culinary close
5.0/5
£309  night
9
4
3
Details View Offers
VILLA SAN GALGANO - Villa San Galgano
£420  night
8
3
3
Details View Offers
An old mill, completely renovated, in the middle of nature
4.7/5
£120  night
4
2
1
Details View Offers
Holiday home with exclusive swimming pool in the Tuscan Maremma
5.0/5
£251  night
6
3
3
Details View Offers