Casole d'Elsa holiday lettings

We found 1,278 holiday rentals — enter your dates for availability

Discover a selection of 40 homes, 63 apartments and other holiday rentals in Casole d'Elsa that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Casole d'Elsa

Showing deals for:12 Jun - 19 Jun

Image gallery for Casa Acacia, an ancient tower nestled in the green hills of San Giminiano

Pool
9.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)

Casa Acacia, an ancient tower nestled in the green hills of San Giminiano

San Gimignano

8% off
Price is £2,051
for 7 nights, 1 room
£293 per night
includes taxes & fees
Casa Acacia, an ancient tower nestled in the green hills of San Giminiano

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The rustic city of Casole d'Elsa awaits you

The countryside and surrounding scenery provide a peaceful ambience to your holiday home in Casole d'Elsa. This city is well-known for its archaeology and spas. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Casole d'Elsa

Do you want to discover top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Casole d'Elsa a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sovestro in Poggio Winery (8.1 mi / 13.1 km)
  • Tenuta Torciano Winery (11.7 mi / 18.8 km)
  • Castello di Monsanto (12.7 mi / 20.5 km)
  • Isole e Olena Winery (14.9 mi / 23.9 km)
  • Casa Sola - Chianti Winery (15.5 mi / 25 km)
  • Casa Emma (15.6 mi / 25.1 km)

Exploring the natural features in Casole d'Elsa

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Casole d'Elsa is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (7.1 mi / 11.4 km)
  • Val di Merse (14.7 mi / 23.6 km)
  • Chianti Sculpture Park (17.2 mi / 27.8 km)
  • I Canaloni del Torrente Farma (18.7 mi / 30.1 km)
  • Hedonistic Hiking (5.2 mi / 8.3 km)
  • Alta Val d'Elsa River Park (5.5 mi / 8.8 km)

Travelling to and around Casole d'Elsa

The nearest airport is in Peretola Airport (FLR), located 32.7 mi (52.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Casole D'Elsa when booking a holiday rental?
When considering a holiday rental in Casole D'Elsa, the charming historic centre is a popular area to stay. This picturesque medieval village offers a delightful atmosphere with its narrow cobbled streets and stunning views of the surrounding Tuscan countryside. Within the centre, you'll find a variety of properties, ranging from quaint apartments to elegant villas, suiting different preferences and budgets.

Staying in the historic centre places you within walking distance of several attractions, such as the beautiful Parish Church of San Giovanni Battista, which features remarkable artwork and architecture. Additionally, the nearby Castle of Casole D'Elsa, with its fascinating history, adds to the allure of the area. The village is also known for its delightful local eateries and wine bars, allowing you to immerse yourself in authentic Tuscan cuisine.

Another appealing neighbourhood is the countryside surrounding Casole D'Elsa, which boasts a selection of charming farmhouses and villas. This area provides a peaceful retreat while still being conveniently close to the village. Here, you can enjoy the breathtaking landscapes, with rolling hills and vineyards that are superb for leisurely strolls or cycling.
How much does it cost to rent a holiday home in Casole D'Elsa?
Prices for holiday rentals in Casole D'Elsa 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 Casole D'Elsa 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 Casole D'Elsa holiday house rentals?
You can find great discounts on house rentals in Casole D'Elsa 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 Casole D'Elsa?
In Casole D'Elsa, apartments are the most popular type of holiday rental, with around 444 available throughout this picturesque Tuscan town. Many of these apartments are situated in charming neighbourhoods, providing easy access to local attractions such as the historic centre and the surrounding countryside. Most units come with amenities like fully equipped kitchens, comfortable living areas, and outdoor spaces, allowing guests to enjoy the beautiful Tuscan landscape.

For those seeking more spacious rooms, approximately 228 holiday houses are offered, which are ideal for families or larger groups. These homes typically feature multiple bedrooms, private gardens, and outdoor dining areas, great for enjoying al fresco meals under the Tuscan sun. Additionally, there are around 64 villas and 56 cottages, which provide more luxurious and secluded options for travellers looking for an upscale experience.
Are there any family house rentals in Casole D'Elsa?
In Casole D'Elsa, Tuscany, there are a variety of family-friendly homes available, with around 134 options to choose from. This picturesque village, set amidst the rolling hills of Tuscany, provides an excellent base for families looking to explore the region. Many properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor terraces or gardens where children can play and families can enjoy al fresco dining.

Visitors will appreciate amenities such as Wi-Fi, swimming pools, and sometimes even game rooms, ensuring everyone has a comfortable and enjoyable stay. The surrounding area is rich in natural beauty, with nearby attractions like the historic town of San Gimignano, known for its medieval towers and charming streets, just a short drive away.
Can I rent a holiday home with a pool or hot tub in Casole D'Elsa?
In Casole D'Elsa, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 173 options to choose from. This picturesque town in Tuscany is surrounded by stunning countryside, providing a serene setting for relaxation. Many of the properties come with private swimming pools, inviting hot tubs, and spacious outdoor areas superb for sunbathing or al fresco dining.

Travellers can expect various amenities in these rentals, such as fully equipped kitchens, comfortable living spaces, and often charming rustic decor that reflects the local architecture. Some properties may also offer additional features like barbecue facilities and expansive gardens, allowing guests to fully immerse themselves in the Tuscan lifestyle.
Can I find long-stay holiday rentals in Casole D'Elsa?
A long-stay holiday rental in Casole D'Elsa 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 Casole D'Elsa?
In Casole D'Elsa, travellers will find a variety of pet-friendly house rentals available, with around 75 options to choose from. This charming town in Tuscany offers a delightful mix of rustic charm and modern conveniences, making it an excellent choice for those looking to enjoy a countryside getaway with their pets.

Many of the holiday rentals feature amenities such as spacious gardens, outdoor terraces, and fully equipped kitchens, allowing guests to relax and cook at their leisure. The properties often come with traditional Tuscan architectural elements, providing an authentic experience in a picturesque setting.

The surrounding area is rich in natural beauty, with nearby walking trails and scenic landscapes superb for exploring with pets. Additionally, Casole D'Elsa is well-positioned for visiting local wineries and quaint villages, enhancing the overall experience for guests seeking both relaxation and adventure.
Are there any remote work holiday rentals in Casole D'Elsa?
In Casole D'Elsa, Tuscany, there are numerous holiday rentals suitable for remote work, with around 744 options available throughout the area. This picturesque town, known for its medieval charm and stunning landscapes, provides a serene environment for those looking to combine work and leisure. Many properties come equipped with reliable Wi-Fi, both in rooms and common areas, ensuring that you can stay connected while enjoying the beautiful surroundings.

Travellers can expect amenities such as dedicated workspaces with desks and chairs in some rentals, allowing for a comfortable working setup. Additionally, the area boasts a range of delightful cafes and restaurants nearby, superb for a change of scenery during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Casole D'Elsa holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Casole D'Elsa 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 Casole D'Elsa?
In Casole D'Elsa, popular rental amenities include kitchens, which allow guests to prepare their own meals with local produce. Many properties also offer onsite parking, making it convenient for those travelling by car. A garden is a common feature, providing a lovely outdoor space to relax and enjoy the Tuscan landscape. Additionally, most rentals come equipped with a coffee and tea maker, superb for starting the day with a warm beverage. For those looking to unwind, shared pools are often available, offering a refreshing option for leisurely afternoons.
When is the best time to visit Casole D'Elsa for a holiday rental?
The most popular time to visit Casole D'Elsa is during the summer months of June to August, when the charming Tuscan countryside comes alive with vibrant colours and a lively option. This peak season attracts many travellers eager to indulge in the region's rich history, stunning landscapes, and delicious cuisine. With warm temperatures averaging between 25 to 30 degrees Celsius, it's great for exploring ancient hilltop towns or enjoying outdoor dining at local trattorias.

July, in particular, is a bustling month in Casole D'Elsa. The warm weather allows for leisurely strolls through the enchanting streets, and visitors can partake in various festivals celebrating local traditions. The longer days offer ample time for sightseeing and immersing yourself in the picturesque surroundings.

For those seeking a more affordable option, consider visiting in February. While this month is less crowded, it presents a unique opportunity to enjoy the serene beauty of Tuscany in winter, with temperatures ranging from 0 to 10 degrees Celsius. It's an ideal time for cosy stays, where you can savour local wines and cuisine without the hustle and bustle of peak season.
How early should I book a Casole D'Elsa holiday rental?
Book your Casole D'Elsa 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 Casole D'Elsa?
In Casole D'Elsa, visitors can engage in the stunning Tuscan landscape and rich history. The medieval town itself is a highlight, featuring charming narrow streets, ancient stone buildings, and the impressive Church of San Niccolò, which offers beautiful views of the surrounding countryside.

Nearby, the impressive ruins of the ancient Etruscan settlement of Volterra are only a short drive away, providing a glimpse into the region's historical significance. The enchanting village of San Gimignano, famous for its medieval towers and UNESCO World Heritage status, is also within easy reach and is superb for a day trip.

For those who enjoy outdoor activities, the rolling hills surrounding Casole D'Elsa are ideal for hiking and cycling, with numerous trails that showcase the beautiful vineyards and olive groves typical of Tuscany.
Can I change or cancel my Casole D'Elsa home rental booking on Vrbo?
To find Casole D'Elsa 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 Casole D'Elsa 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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