Roccastrada holiday lettings

We found 963 holiday rentals — enter your dates for availability

Discover a selection of 67 homes, 38 apartments and other holiday rentals in Roccastrada that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

Delight in the natural landscape of Roccastrada

The area's culture and history are just some of the reasons to come on holiday to Roccastrada. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Roccastrada

Do you want to discover attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Roccastrada a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Podere Ristella Vineyards and Winery (6 mi / 9.6 km)
  • Terme Petriolo (7.9 mi / 12.8 km)
  • Castello Banfi (11.9 mi / 19.2 km)
  • Castiglion del Bosco Winery (13.5 mi / 21.7 km)
  • Poggio Antico (15.5 mi / 24.9 km)
  • Tenuta Greppo Franco Biondi Santi (17.1 mi / 27.5 km)

Exploring the natural landscape of Roccastrada

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Roccastrada is a great place to get outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • I Canaloni del Torrente Farma (5.5 mi / 8.8 km)
  • Val di Merse (11.8 mi / 19 km)
  • Lago dell'Accesa (13.8 mi / 22.2 km)
  • Natural Reserve Diaccia Botrona (21.5 mi / 34.6 km)
  • Cala Violina (22.6 mi / 36.3 km)
  • Le Biancane (18.6 mi / 29.9 km)

How to get to and around Roccastrada

If you prefer train travel, make your way to Roccastrada Station or Sticciano Station to see more of the city.

Frequently asked questions

What is the best area to stay in Roccastrada when booking a holiday rental?
When considering a holiday rental in Roccastrada, Tuscany, a popular area to stay is the charming village itself, which is known for its picturesque streets and rich history. The village is home to a variety of properties, offering options that cater to different tastes and budgets. Staying in the heart of Roccastrada allows you to immerse yourself in local culture and enjoy easy access to delightful cafés and restaurants.

Nearby attractions include the stunning Rocca di Frassinello, a modern architectural marvel set among the vineyards, where wine enthusiasts can indulge in tastings and tours. Additionally, the surrounding countryside is great for exploring the natural beauty of Tuscany, with scenic walking trails and breathtaking views of the hills.

Another attractive area is the surrounding countryside, which features numerous farms and traditional villas. This setting provides a tranquil escape and an opportunity to experience the authentic Tuscan lifestyle. Here, you can enjoy outdoor activities, including hiking and cycling, while soaking in the serene landscapes.
How much does it cost to rent a holiday home in Roccastrada?
Prices for holiday rentals in Roccastrada vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Roccastrada to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Roccastrada holiday house rentals?
You can find great discounts on house rentals in Roccastrada on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Roccastrada?
In Roccastrada, holiday houses are the most popular type of holiday rental, with about 165 available in picturesque settings throughout the Tuscan countryside. These spacious homes typically feature multiple bedrooms, fully equipped kitchens, and outdoor areas such as gardens or terraces, superb for enjoying the stunning views of the surrounding hills. Additionally, there are around 87 apartments available, often located in charming buildings that offer a more intimate feel. Many of these apartments come with modern amenities, comfortable living spaces, and some may even have balconies to soak in the Tuscan sun. Villas are also a sought-after option, with about 81 options that often include luxurious features like private pools and expansive grounds.
Are there any family house rentals in Roccastrada?
In Roccastrada, Tuscany, there are some available family-friendly house rentals, with around 52 options to choose from. The area is known for its stunning countryside and charming villages, making it an excellent choice for families looking to explore the beauty of Tuscany.

Many of these properties offer spacious living areas, fully equipped kitchens, and outdoor spaces where children can play or families can dine al fresco. Visitors can often find amenities such as Wi-Fi, air conditioning, and private gardens or terraces, ensuring a comfortable stay.

The nearby towns of Roccastrada and Massa Marittima provide opportunities for cultural exploration, with historic sites, local markets, and delightful restaurants serving traditional Tuscan cuisine.
Can I rent a holiday home with a pool or hot tub in Roccastrada?
In Roccastrada, Tuscany, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 61 options to choose from. This picturesque area is located in the heart of the Tuscan countryside, offering a serene environment for relaxation and exploration. Many of these properties feature private swimming pools, outdoor terraces, and hot tubs, superb for unwinding after a day of sightseeing or enjoying the stunning views of the rolling hills.

Travellers can expect a variety of amenities in these rentals, including spacious living areas, fully equipped kitchens ideal for preparing local Tuscan delicacies, and outdoor dining spaces that make for enjoyable al fresco meals. Some properties may also provide additional features like barbecue facilities, gardens, and proximity to hiking trails, enhancing the overall holiday experience.
Can I find long-stay holiday rentals in Roccastrada?
A long-stay holiday rental in Roccastrada is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Roccastrada?
In Roccastrada, Tuscany, there are a variety of pet-friendly house rentals available, with around 71 options to choose from. This charming area is surrounded by picturesque landscapes, offering a serene atmosphere great for a getaway with pets. Many of the holiday rentals in Roccastrada come equipped with amenities such as private gardens, outdoor seating areas, and fully equipped kitchens, ensuring a comfortable stay for both you and your furry companions.

The town is well-situated for exploring the beautiful Tuscan countryside, with opportunities for hiking and enjoying nature walks that are suitable for pets. Furthermore, the nearby towns and villages often have local parks and green spaces where you can take your dog for a stroll.
Are there any remote work holiday rentals in Roccastrada?
In Roccastrada, Tuscany, there is a considerable selection of remote work holiday rentals available, with around 309 options to choose from. This picturesque area offers a serene environment, ideal for those looking to combine work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, making it convenient for remote work. Additionally, you can expect comfortable living spaces, often featuring well-furnished areas for productivity.

The town itself is surrounded by beautiful countryside, where you can enjoy stunning views and explore local attractions. Nearby, you can find charming villages and opportunities for outdoor activities such as hiking and cycling. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Roccastrada holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Roccastrada with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Roccastrada?
In Roccastrada, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals and enjoy the local cuisine. Many properties also offer onsite parking, making it convenient for travellers with vehicles. For those bringing along furry companions, several rentals permit pets, ensuring that no one has to be left behind. Additionally, some accommodations cater to service animals. To enhance the cosy atmosphere, many rentals feature fireplaces, superb for warming up after a day of exploring the stunning Tuscan countryside.
When is the best time to visit Roccastrada for a holiday rental?
The best time to visit Roccastrada for a holiday rental is during the summer months, particularly in July. This peak season, which runs from July to September, attracts visitors eager to explore the picturesque hills of Tuscany and experience the vibrant local culture. With warm temperatures averaging around 30°C, it's an ideal time for outdoor activities, leisurely strolls through charming medieval streets, and indulging in exquisite local cuisine at al fresco dining spots.

July stands out as the most popular month, bustling with life and offering a number of events, including local festivals and markets. The atmosphere is lively, making it a great backdrop for those looking to immerse themselves in the Tuscan lifestyle while enjoying the stunning landscapes.

For those seeking a more tranquil experience, consider visiting in December. Although this month falls outside the high tourist season, it offers a unique charm with fewer crowds and the opportunity to enjoy the serene beauty of Roccastrada during the winter months. The festive spirit is palpable, and you can savour the local holiday traditions while exploring the enchanting countryside.

Ultimately, your choice of when to visit Roccastrada hinges on whether you prefer the vibrant energy of summer or the peaceful ambiance of winter.
How early should I book a Roccastrada holiday rental?
Book your Roccastrada holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roccastrada?
In Roccastrada, visitors can engage in the stunning landscapes and rich history of Tuscany. The charming medieval village itself offers a glimpse into the region's past, with its narrow streets and historic architecture, including the impressive Church of San Nicola. Nearby, the scenic hills provide ample opportunities for hiking and enjoying the tranquil countryside.

Just a short drive away, the picturesque town of Massa Marittima is well worth a visit, known for its striking cathedral and the medieval Piazza Garibaldi. The surrounding area is dotted with vineyards and olive groves, making it ideal for wine and olive oil tasting tours that showcase the local produce.

For those interested in outdoor activities, the Montemassi Castle ruins offer a fantastic viewpoint of the surrounding landscape, while the nearby natural parks, such as the Parco Nazionale delle Colline Metallifere, provide trails for walking and cycling amidst unspoiled nature.

Additionally, the coastal town of Follonica, located a bit further away, boasts beautiful beaches and a lively promenade, great for a day trip to experience the Tuscan coast.
Can I change or cancel my Roccastrada home rental booking on Vrbo?
To find Roccastrada holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roccastrada holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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