Roccastrada vacation rentals
Vacation rentals in Roccastrada by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.
In Roccastrada, discover the ancient village charm of Montemassi Castle, the calming landscapes of Maremma Regional Park, and the panoramic views from Monte Amiata. Travelers visit for Tuscan culinary experiences, traditional festivals like the Giostra di Monticiano, and wine tasting in local vineyards. Houfy connects you directly with hosts in Roccastrada. Choose from countryside villas, rustic farmhouses, and village apartments in nearby towns like Gavorrano and Grosseto. The best months to visit are May and September, when the weather is pleasant, and local festivities are in full swing.
Recommended Homes in Roccastrada
Handpicked properties we think you'll love in Roccastrada.
€553.00 EUR total for 3 nights
Apr 25 – 28, 2027
€1,624.00 EUR total for 7 nights
May 29 – Jun 5, 2027
€245.00 EUR total for 3 nights
Nov 15 – 18, 2026
Why visit Roccastrada
Discover what makes Roccastrada a perfect vacation rental destination.
Explore Ancient Fortresses
Historic castles abound here.
Visit the Castel di Pietra, a medieval fortress just 5 miles from Roccastrada. Explore its rich history and stunning views of the Tuscan landscape.
Stunning Natural Landscapes
Vibrant nature in Maremma's heart.
Discover Riserva Naturale Farma, an enchanting forest reserve 15 miles south, offering hiking trails amidst scenic oak and beech forests.
Savor Authentic Tuscan Cuisine
Traditional flavors meet local wines.
Enjoy a meal at Ristorante La Tinaia, known for its homemade pasta and local wines, located in the center of Roccastrada.
Engage in Local Traditions
Cultural festivals year-round.
Attend the annual Roccastrada Festival in August, featuring music, dance, and authentic regional food celebrating Tuscan heritage.
Where to stay in Roccastrada
The best areas and neighborhoods for your vacation rental in Roccastrada.
Centro Storico
The historic heart of Roccastrada, featuring medieval architecture and local eateries. Ideal for history buffs and food lovers.
Ribolla
A quaint town known for its mining history and cultural sites, located 8 miles from Roccastrada. Perfect for a quiet retreat.
Montemassi
Iconic for the Montemassi Castle. Offers spectacular views and is ideal for history enthusiasts.
Sticciano
A picturesque village with breathtaking views of the Maremma region. Known for its serene environment.
Roccastrada vacation rentals with free WiFi, air conditioning or kids friendly
Free WiFi, air conditioning, kids friendly and more — every Roccastrada vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Roccastrada
All within driving distance of Roccastrada vacation rentals.
Castel di Pietra
A medieval castle offering a glimpse into Roccastrada's ancient past. · 5 miles
Riserva Naturale Farma
A forest reserve perfect for hiking and nature walks. · 15 miles
Roccastrada Festival
An annual event showcasing local music and dance. · 0 miles
Ristorante La Tinaia
Famous for homemade pasta and local wines. · 0 miles
Monte Leoni
A mountain offering hiking trails and panoramic views. · 10 miles
Parco Minerario Naturalistico Gavorrano
A mining park with outdoor exhibits and tours. · 12 miles
Getting to and around Roccastrada
Roccastrada is accessible by car with nearby regional airports for easy travel.
- GROSSETO AIRPORT
- Located 25 miles from Roccastrada, offers limited domestic flights and charter services.
- PISA INTERNATIONAL AIRPORT
- About 85 miles away, providing extensive international flights and connections.
- LOCAL ROADS
- Roccastrada is well-connected via SP157 and SP19, making car travel convenient.
- BUS SERVICES
- Local buses connect Roccastrada to Grosseto and other nearby towns.
Similar vacation rentals near Roccastrada
Homes within 60 miles of Roccastrada, from verified hosts.
€1,566.00 EUR total for 3 nights
Nov 15 – 18, 2026
€360.00 EUR €306.00 EUR total for 3 nights
Nov 15 – 18, 2026
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/c818c0e5340be04d67bff39c3fbd6563.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/f8e82171432ea6c1ab3abdc9c1d649ae.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/9642a01fb6df6335689a4521dc1fe943.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/0499d8d73ec2756035fb97138059512c.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/60ec106ed2d8d6bc428db79190ab40f2.jpg?im_w=480)
€647.50 EUR total for 5 nights
Nov 16 – 21, 2026
€260.00 EUR total for 3 nights
Nov 15 – 18, 2026
€180.00 EUR €162.00 EUR total for 3 nights
Nov 15 – 18, 2026
€527.63 EUR total for 5 nights
Nov 15 – 20, 2026
€626.25 EUR total for 3 nights
May 29 – Jun 1, 2027
€594.75 EUR total for 3 nights
May 29 – Jun 1, 2027
€642.00 EUR total for 3 nights
May 29 – Jun 1, 2027
€642.00 EUR total for 3 nights
May 29 – Jun 1, 2027
€642.00 EUR total for 3 nights
May 29 – Jun 1, 2027
€579.00 EUR total for 3 nights
May 29 – Jun 1, 2027
Explore near Roccastrada
Cities and towns within driving distance of Roccastrada, each bookable direct with the host.
Why guests book on Houfy
Direct with the host
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Itemised pricing
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Frequently asked questions
Quick answers about booking vacation rentals in Roccastrada and what direct booking on Houfy actually means.
Vacation rentals in Roccastrada typically range from €70 to €150 per night, depending on size and location.
Yes, several rentals welcome pets. Ensure to check the rental listing on Houfy for specific pet policies.
Centro Storico is excellent for history enthusiasts, while Montemassi provides stunning views and a quieter stay.
Spring and autumn offer pleasant weather and fewer crowds, making them ideal for visiting Roccastrada.
In Roccastrada, guests can find villas, rustic apartments, and traditional Tuscan homes for rent on Houfy.
Rentals offer more space and the flexibility to cook, often at a lower cost compared to hotels in the area.
Roccastrada is known for its medieval architecture, vibrant local festivals, and stunning landscapes unique to Tuscany.
Houfy is a direct booking platform where guests book directly from owners, paying the listed price.
Yes, Houfy allows safe direct communication between guests and hosts, ensuring a transparent booking process.