Roccastrada holiday lettings

We found 954 holiday rentals — enter your dates for availability

Discover a selection of 64 homes, 41 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.

Holiday rentals with weekly discounts - Roccastrada

Showing deals for:13 Feb - 20 Feb

Image gallery for Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi

Monticiano, Toscana

14% off
Price is £8,479
for 7 nights, 1 villa
£1,211 per night
includes taxes & fees
Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi

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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)
  • Piscina Il Giunco (11.5 mi / 18.5 km)
  • Castello Banfi (11.9 mi / 19.2 km)
  • Castiglion del Bosco Winery (13.5 mi / 21.7 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)
  • Lago dell'Accesa (13.2 mi / 21.3 km)
  • Natural Reserve Diaccia Botrona (21.5 mi / 34.6 km)
  • State Natural Reserve Tomboli Follonica (21.9 mi / 35.2 km)
  • Cala Violina (22.6 mi / 36.3 km)
  • Val di Merse (11.8 mi / 19 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, the charming area of Sticciano stands out as an excellent choice. This quaint village offers a delightful blend of rustic charm and local culture, making it an ideal base for exploring the stunning landscapes of the Maremma region. One of the top attractions nearby is the beautiful Abbey of San Lorenzo al Lanzo, a serene spot that showcases impressive architecture and a tranquil atmosphere superb for contemplation.
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.
Where are the best areas for renting a beach house in Roccastrada?
For renting a beach house in Roccastrada, Tuscany, travellers should consider the nearby coastal areas of the Maremma region, particularly around towns like Castiglione della Pescaia and Punta Ala, which are easily accessible from Roccastrada. These seaside towns offer a range of holiday rentals, from charming villas to modern apartments, many of which come with amenities such as private terraces, outdoor dining areas, and swimming pools, superb for enjoying the Mediterranean climate.

In Castiglione della Pescaia, visitors can find properties close to the sandy beaches, with some featuring direct beach access and stunning sea views. Many rentals here are equipped with fully stocked kitchens, allowing for self-catering, and spacious living areas ideal for family gatherings. The town itself is lively, with a variety of local restaurants, cafes, and shops, providing a delightful atmosphere for holidaymakers.

Punta Ala, known for its upscale vibe, hosts elegant villas that often include private gardens and easy access to nearby golf courses. Properties in this area may also offer amenities like air conditioning, Wi-Fi, and proximity to beach clubs, making them ideal for those seeking a luxurious beachside experience.
What is the most popular type of holiday rental accomodation in Roccastrada?
In Roccastrada, holiday houses are the most popular rental choice, with around 52 available throughout the charming Tuscan countryside. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, allowing guests to enjoy a home-cooked meal while taking in the beautiful surroundings. Many also come with outdoor spaces, such as gardens or terraces, superb for al fresco dining or relaxing under the Tuscan sun.

Apartments are also a common option, with about 28 available, often located within the quaint village centre, providing easy access to local shops and eateries. These apartments generally include kitchen facilities, comfortable seating areas, and some may offer stunning views of the surrounding hills.
Are there any family house rentals in Roccastrada?
In Roccastrada, Tuscany, there is a popular selection of family-friendly holiday rentals—around 54 to choose from. This charming area is surrounded by picturesque countryside and offers a unique blend of rustic charm and modern amenities, making it an ideal spot for families. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy themselves in a safe environment.
Can I rent a holiday home with a pool or hot tub in Roccastrada?
In Roccastrada, Tuscany, there are many holiday homes available for rent that come equipped with pools or hot tubs, with around 66 options to consider. This picturesque area is surrounded by beautiful countryside and rolling hills, making it an ideal spot for relaxation. Numerous properties feature private swimming pools, often accompanied by spacious outdoor terraces ideal for sunbathing or alfresco dining. Many rentals also offer hot tubs, providing a great way to unwind after a day of exploring the charming local villages and stunning landscapes.
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 numerous pet-friendly house rentals available, with around 69 options to choose from. This picturesque area offers a range of holiday homes that often come equipped with amenities such as private gardens, outdoor dining areas, and fully equipped kitchens, providing a comfortable stay for both travellers and their pets. Many properties feature rustic charm, including exposed beams and traditional Tuscan decor, creating a warm and inclusive setting.
Are there any remote work holiday rentals in Roccastrada?
In Roccastrada, Tuscany, there are numerous remote work holiday rentals available, with around 104 options to choose from. This charming town, surrounded by the picturesque Tuscan countryside, provides a tranquil setting for those looking to combine work and leisure. Many properties are equipped with amenities tailored for remote work, including high-speed Wi-Fi, dedicated desk spaces, ergonomic chairs, and even laptop-compatible safes for security. 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, which feature essential cookware, dishware, and utensils, allowing guests to prepare their own meals. Many rentals also come with refrigerators and ovens, enhancing the convenience for those who enjoy cooking. Additionally, free Wi-Fi is commonly available, enabling visitors to stay connected during their stay.
When is the best time to visit Roccastrada for a holiday rental?
July marks the peak season for visiting Roccastrada, Tuscany, drawing travellers eager to immerse themselves in the region's stunning landscapes and rich cultural heritage. During these summer months, particularly from July to September, visitors can bask in warm temperatures, often reaching the high 20s Celsius, making it ideal for outdoor activities such as hiking through the picturesque hills or exploring the charming medieval villages nearby.

July is particularly vibrant, with numerous festivals and events that showcase local traditions, providing an authentic experience for those seeking to connect with the Tuscan lifestyle. The long days and pleasant evenings create the superb setting for al fresco dining, where you can savour delicious local cuisine paired with exquisite wines.

For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, generally around 10 degrees Celsius, this month offers a unique perspective on Roccastrada, with fewer tourists and a tranquil atmosphere. You can enjoy the holiday decorations and experience the local traditions during the festive season, all while avoiding the crowds.
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 enchanting landscapes of Tuscany, where rolling hills and vineyards create a picturesque backdrop. The town itself offers charming holiday rentals with traditional Tuscan architecture, allowing guests to enjoy a taste of local culture.

A stroll through the historic centre reveals quaint streets, local shops, and delightful eateries serving authentic Italian cuisine. Nearby, the stunning medieval village of Montemassi is well worth a visit, known for its ancient castle ruins that provide spectacular views of the surrounding countryside.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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