Castiglione d'Orcia holiday rentals

We found 1,348 holiday rentals — enter your dates for availability
Select from 35 houses, 53 apartments and other holiday rentals to find the perfect place for your stay in Castiglione d'Orcia. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as a fireplace and garden. Whatever you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Castiglione d'Orcia

Showing deals for:18 Dec - 25 Dec

Outdoor dining
Pool
Dining
Living area
Exceptional
(14 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Montalcino

10% off
AU$26,247
for 7 nights, 1 villa
AU$3,750 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Room
Private kitchen
Exterior
Private kitchen
Exceptional
(11 reviews)

"Il Focolare" Superior Apartment in Monticchiello

Pienza

5% off
AU$1,252
for 7 nights, 1 home
AU$179 per night
includes taxes & fees
"Il Focolare" Superior Apartment in Monticchiello
Dining
Pool
Exterior
Exterior detail
Exceptional
(17 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

8% off
AU$6,105
for 7 nights, 1 villa
AU$872 per night
includes taxes & fees
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Large kitchen
Pool
Exterior
Outdoor dining
Exceptional
(52 reviews)

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pienza

9% off
AU$5,589
for 7 nights, 1 villa
AU$798 per night
includes taxes & fees
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Interior
Property grounds
Exterior
Pool
Exceptional
(12 reviews)

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Radicofani

9% off
AU$3,861
for 7 nights, 1 home
AU$552 per night
includes taxes & fees
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Exterior
Pool
Exterior detail
Interior
Wonderful
(5 reviews)

Il Seccatoio – Independent rustic house with valley view and natural pool

Santa Fiora

9% off
AU$1,155
for 7 nights, 1 cottage
AU$165 per night
includes taxes & fees
Il Seccatoio – Independent rustic house with valley view and natural pool
Dining
Outdoor dining
from North, access to the kitchen-lounge
Property grounds
Exceptional
(38 reviews)

Villa Mulinello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
AU$2,247
for 7 nights, 1 home
AU$321 per night
includes taxes & fees
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Private kitchen
Exterior
Living area
Property grounds
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
AU$2,495
for 7 nights, 1 home
AU$356 per night
includes taxes & fees
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Room
Outdoor dining
Living area
Private kitchen
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

9% off
AU$3,158
for 7 nights, 1 apartment
AU$451 per night
includes taxes & fees
Magnificent and Bright 2 BR Apt. with Terrace
Interior
Gorgeous View to wake up to in the mornings!
Classic Apt. in a Palazzo with modern comforts and classic features
Interior
Exceptional
(36 reviews)

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Montepulciano

13% off
AU$3,995
for 7 nights, 1 apartment
AU$571 per night
includes taxes & fees
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Delight in the natural landscape of Castiglione d'Orcia

The hot springs, countryside and waterfalls are the perfect backdrop to your holiday home in Castiglione d'Orcia. Travellers especially like the spas, hiking and gardens in this relaxing and walkable city. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Castiglione d'Orcia

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that makes Castiglione d'Orcia a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tenuta Greppo Franco Biondi Santi (6.3 mi / 10.1 km)
  • Baths of San Filippo (6.9 mi / 11.1 km)
  • Piscine Termali Theia (10.1 mi / 16.2 km)
  • Consorzio del Vino Nobile di Montepulciano (10.2 mi / 16.5 km)
  • Terme di Chianciano (10.5 mi / 16.8 km)
  • Castello Banfi (11.1 mi / 17.8 km)

Exploring the natural landscape of Castiglione d'Orcia

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Castiglione d'Orcia. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Historic Centre of Pienza (5.8 mi / 9.3 km)
  • Garden of Daniel Spoerri (6.2 mi / 10 km)
  • Monte Amiata (8.3 mi / 13.3 km)
  • La Foce (8.3 mi / 13.4 km)
  • Piscine Termali Theia (10.1 mi / 16.2 km)
  • Mount Amiata Fauna Park (10.1 mi / 16.3 km)

Frequently asked questions

What is the best area to stay in Castiglione D'Orcia when booking a holiday rental?
When considering a holiday rental in Castiglione D'Orcia, the charming historic centre is the best area to stay. This picturesque village is located in the rolling hills of Tuscany and offers a delightful blend of rustic charm and cultural richness. The historic centre is characterised by its narrow cobbled streets, ancient stone buildings, and stunning views of the surrounding countryside, making it a truly enchanting place to explore.One of the top attractions in the area is the impressive Fortress of Tentennano, which provides panoramic vistas of the Val d'Orcia. Additionally, the nearby thermal baths offer a superb opportunity for relaxation, allowing visitors to unwind in naturally warm waters while enjoying the beautiful landscapes.In terms of holiday rentals, the historic centre boasts a variety of properties, from quaint apartments in restored buildings to charming villas with gardens. This area serves as a fantastic base for discovering the local cuisine, enjoying wine tastings, and exploring nearby attractions such as the beautiful towns of Pienza and Montalcino.
What is the most popular type of holiday rental accomodation in Castiglione D'Orcia?
In Castiglione D'Orcia, apartments are the most popular type of holiday rental, with approximately 152 options available. These apartments are typically situated in charming neighbourhoods, offering easy access to local attractions and breathtaking views of the Tuscan countryside. Most rentals include essential amenities such as fully equipped kitchens, comfortable living areas, and many also feature outdoor spaces like balconies or patios, great for enjoying the scenic surroundings.Additionally, there are around 108 villas and 92 holiday houses that cater to travellers seeking more space and privacy. These properties often come with multiple bedrooms, private gardens, and sometimes even pools, making them ideal for families or groups. Cottages are also available, providing a quaint and rustic option for those looking to immerse themselves in the tranquil Tuscan landscape.
Are there any family house rentals in Castiglione D'Orcia?
In Castiglione D'Orcia, Tuscany, there are numerous family-friendly house rentals available, with around 40 options to choose from. This charming village is surrounded by stunning landscapes and offers a wealth of cultural experiences for families to enjoy. Many of these properties feature spacious living areas, well-equipped kitchens, and outdoor terraces or gardens, which are superb for children to play in.Visitors will find amenities such as Wi-Fi and air conditioning to ensure a comfortable stay. Additionally, the locale is close to enchanting sites like the historic Abbey of Sant'Antimo and the picturesque Val d'Orcia, where families can explore beautiful hiking trails and picturesque towns.
Can I rent a holiday home with a pool or hot tub in Castiglione D'Orcia?
In Castiglione D'Orcia, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 59 options to choose from. This picturesque village in Tuscany is surrounded by stunning landscapes, making it an ideal location for a relaxing getaway. Many of the properties come with private swimming pools, superb for cooling off during the warm summer months, as well as hot tubs for unwinding after a day of exploring the beautiful countryside.Travellers can expect various amenities in these rentals, including spacious outdoor areas, fully equipped kitchens for self-catering, and comfortable living spaces designed for relaxation. Some properties may also offer stunning views of the rolling hills and nearby vineyards, enhancing the overall experience of staying in this charming Tuscan village.
Are there pet-friendly house rentals in Castiglione D'Orcia?
In Castiglione D'Orcia, there are numerous pet-friendly house rentals available, with around 57 options to choose from. This charming town in Tuscany offers a variety of accommodations, including rustic villas and traditional farmhouses that often feature beautiful views of the surrounding hills. Many of these properties come equipped with amenities such as kitchens, outdoor spaces, and comfortable living areas, ideal for both relaxation and entertaining.The area is known for its stunning landscapes, which provide ample opportunities for outdoor activities with pets. Nearby, the Val d'Orcia Natural Park offers scenic walking trails and breathtaking vistas, making it a great spot for leisurely hikes with your furry companions. Additionally, the town itself is rich in history and culture, with quaint streets, local markets, and delightful eateries that welcome pets, enhancing the overall experience for travellers with animals.
Are there any remote work holiday rentals in Castiglione D'Orcia?
In Castiglione D'Orcia, there are numerous remote work holiday rentals available, with around 320 properties suited for those looking to combine work and leisure. This picturesque area in Tuscany offers a tranquil environment, superb for productivity. Many rentals come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, ensuring a conducive atmosphere for remote working.The town itself is surrounded by stunning landscapes and historic sites, making it easy to unwind after a day of work. Nearby attractions include the beautiful Val d'Orcia, known for its rolling hills and classic Tuscan scenery. Travellers can also explore local vineyards and charming villages, adding cultural richness to their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Castiglione D'Orcia?
In Castiglione D'Orcia, popular rental amenities include well-equipped kitchens, great for those who enjoy cooking with local ingredients. Many properties feature inviting fireplaces, creating a warm and cosy atmosphere during cooler evenings. For travellers bringing their furry friends, several rentals permit pets, ensuring a family-friendly experience. Onsite parking is a common convenience, allowing guests to explore the beautiful Tuscan countryside without hassle. Additionally, properties accommodating service animals provide an inclusive environment for all guests.
When is the best time to visit Castiglione D'Orcia for a holiday rental?
The best time to visit Castiglione D'Orcia for a holiday rental is during the peak season from March to May. March stands out as a particularly popular month, as visitors flock to this enchanting Tuscan village to witness the breathtaking landscapes coming to life with vibrant spring colours. The temperatures during this time typically range from 8 to 20 degrees Celsius, providing a comfortable climate for outdoor activities and sightseeing.During these months, you can indulge in leisurely strolls through the picturesque streets, exploring the rich history and stunning architecture that the area has to offer. The nearby Val d'Orcia region is great for wine tasting and sampling delicious local cuisine, making it an ideal destination for those seeking a blend of adventure and culinary delights.If you're looking for a more budget-friendly experience, consider visiting in December. While this is the low season, you can still enjoy the charm of Castiglione D'Orcia adorned in festive decorations. The quieter atmosphere allows for a more intimate experience of this beautiful region, great for those who appreciate serene exploration.Ultimately, your choice of when to visit will depend on whether you prefer the lively ambience of springtime festivities or the tranquil beauty of winter's embrace.
What are the top attractions in Castiglione D'Orcia?
In Castiglione D'Orcia, visitors can take part in the stunning landscapes of Tuscany, characterised by rolling hills and picturesque vineyards. The village itself is a UNESCO World Heritage Site, celebrated for its well-preserved medieval architecture and stunning views. One of the top attractions is the Fortress of Tentennano, which offers panoramic views of the surrounding countryside and is a great spot for photography enthusiasts.Additionally, the nearby Val d'Orcia region is renowned for its natural beauty and is dotted with charming towns such as Pienza and Montalcino, famous for its Brunello wine. Visitors can explore the beautiful landscapes by hiking or cycling along the scenic routes. The area is also rich in thermal springs, with places like Bagno Vignoni providing relaxing experiences in natural hot waters, making it an excellent choice for wellness seekers.
Are all fees included in the Castiglione d'Orcia holiday homes prices shown on Stayz?
Stayz 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.
Are there any Castiglione d'Orcia holiday homes with parking?
Stayz offers a wide selection of holiday homes in Castiglione d'Orcia 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 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.
Are there any discounts for Castiglione d'Orcia holiday homes?
You can find great discounts on holiday homes in Castiglione d'Orcia on Stayz, 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.
Can I change or cancel my Castiglione d'Orcia holiday home booking on Stayz?
To find Castiglione d'Orcia holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Castiglione d'Orcia?
A long-stay holiday home in Castiglione d'Orcia 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Castiglione d'Orcia holiday home?
Book your Castiglione d'Orcia holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Castiglione d'Orcia?
Prices for holiday homes in Castiglione d'Orcia 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Castiglione d'Orcia to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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