Sinalunga holiday rentals

We found 2,009 holiday rentals — enter your dates for availability
Discover a selection of 11 homes, 14 apartments and other holiday rentals in Sinalunga that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Sinalunga

Showing deals for:18 Dec - 25 Dec

Private kitchen
Pool
Dining
Outdoor dining
Exceptional
(14 reviews)

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

Montalcino

10% off
AU$26,244
for 7 nights, 1 villa
AU$3,749 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Room
Private kitchen
Private kitchen
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
Outdoor dining
Exterior detail
Exterior
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
AU$1,513
for 7 nights, 1 room
AU$216 per night
includes taxes & fees
Apartment in Farmhouse
Private kitchen
Exterior
Property grounds
Outdoor dining
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
AU$2,494
for 7 nights, 1 home
AU$356 per night
includes taxes & fees
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Pool
Property grounds
Interior
Outdoor dining
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
AU$7,015
for 7 nights, 1 villa
AU$1,002 per night
includes taxes & fees
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Dining
Outdoor dining
Property grounds
from North, access to the kitchen-lounge
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.
Welcome to a piece of history!
There's no doubt you're in Tuscany
The master bedroom promises privacy
We've tailored every detail to help you feel at home
Exceptional
(24 reviews)

Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

Castiglion Fiorentino

9% off
AU$1,518
for 7 nights, 1 apartment
AU$217 per night
includes taxes & fees
Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities
Room
Interior
AHHH! Tuscany!
Relax in this cozy living area
Exceptional
(11 reviews)

❤️ of Castiglion Fiorentino

Castiglion Fiorentino

9% off
AU$1,141
for 7 nights, 1 apartment
AU$163 per night
includes taxes & fees
❤️ of Castiglion Fiorentino
Bathroom
Outdoor dining
Room
Living area
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
Exterior
Outdoor dining
Property grounds
Pool
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
AU$2,488
for 7 nights, 1 room
AU$355 per night
includes taxes & fees
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
Classic Apt. in a Palazzo with modern comforts and classic features
Gorgeous View to wake up to in the mornings!
Interior
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

Travel to culturally rich Sinalunga

Enjoy the area's culture, wineries and history with a rental holiday home in Sinalunga. This city's cheese shops, local tours and horse riding draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Sinalunga

Are you hoping to discover attractions to see in the area? Venture out of your cosy holiday rental and check out everything that makes Sinalunga a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Consorzio del Vino Nobile di Montepulciano (8.6 mi / 13.8 km)
  • Terme Antica Querciolaia (8.6 mi / 13.8 km)
  • San Giovanni Terme Rapolano (8.7 mi / 14 km)
  • Piscine Termali Theia (12.3 mi / 19.7 km)
  • Terme di Chianciano (12.5 mi / 20.1 km)
  • Valdorcia Terre Senesi (14.7 mi / 23.6 km)

Exploring the natural features in Sinalunga

Whether you're looking for adventure or just want to take in the scenery, Sinalunga is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Terme Antica Querciolaia (8.6 mi / 13.8 km)
  • Historic Centre of Pienza (9.8 mi / 15.8 km)
  • Val di Chiana (9.8 mi / 15.8 km)
  • Terme di Montepulciano Spa (10.2 mi / 16.4 km)
  • Terme Sant'Elena (11.6 mi / 18.7 km)
  • Piscine Termali Theia (12.3 mi / 19.7 km)

How to get to and around Sinalunga

If you're travelling by train, make your way to Sinalunga Station or Sinalunga Rigomagno Station to see more of the city.

Frequently asked questions

What is the best area to stay in Sinalunga when booking a holiday rental?
When considering a holiday rental in Sinalunga, Tuscany, the best area to stay is typically around the town centre. This region offers a charming atmosphere characterised by its quaint streets and historic architecture, making it an ideal base for exploring the local culture. You will find a variety of properties available, ranging from traditional villas to modern apartments, suiting different preferences and budgets.One of the top attractions in the area is the stunning Church of San Bartolomeo, known for its beautiful frescoes and serene ambiance, providing a glimpse into the town's rich history. Additionally, the nearby Val di Chiana is renowned for its breathtaking landscapes and picturesque vineyards, great for those wishing to explore the scenic countryside either on foot or by bike.Staying in the town centre also means easy access to local eateries, where you can savour authentic Tuscan cuisine, as well as markets where you can experience the vibrant local culture.
What is the most popular type of holiday rental accomodation in Sinalunga?
In Sinalunga, villas are the most popular type of holiday rental, with around 144 available throughout the beautiful Tuscan countryside. These villas typically feature spacious layouts with multiple bedrooms, private gardens, and often a swimming pool, providing an ideal setting for families or groups looking to enjoy the serene landscape. Additionally, there are approximately 64 apartments scattered across the town, offering a more intimate stay with amenities like fully equipped kitchens and cosy living areas, great for couples or solo travellers. For those seeking a great experience, about 36 holiday houses and 12 cottages are also available, each providing a charming home-away-from-home atmosphere.
Are there any family house rentals in Sinalunga?
In Sinalunga, Tuscany, there are numerous family-friendly house rentals available, with around 41 options to choose from. This charming town, located in the picturesque landscape of the Val di Chiana, offers a variety of properties suitable for families. Many homes feature spacious living areas, fully equipped kitchens for preparing delightful Italian meals, and outdoor spaces that provide a safe environment for children to play.Visitors will appreciate the proximity to local attractions, including historical sites and beautiful countryside. Families can explore nearby towns such as Montepulciano and Pienza, known for their stunning architecture and local cuisine. Additionally, the surrounding vineyards and olive groves offer opportunities for leisurely strolls and educational experiences about Tuscan farming traditions.
Can I rent a holiday home with a pool or hot tub in Sinalunga?
In Sinalunga, Tuscany, there are plenty of holiday homes available for rent with pools, with around 39 options to choose from. This picturesque area offers a charming rural setting, ideal for those seeking a relaxing getaway. Many of these properties come equipped with private swimming pools, providing a great spot for families or groups to unwind and enjoy the Tuscan sun.Travellers can also expect amenities such as spacious gardens, outdoor dining areas, and fully equipped kitchens, which make self-catering enjoyable. Some rentals may even include hot tubs, enhancing the overall experience of relaxation after a day of exploring the stunning landscape.
Are there pet-friendly house rentals in Sinalunga?
In Sinalunga, Tuscany, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. These holiday homes typically feature amenities such as fully equipped kitchens, private gardens, and outdoor dining areas, allowing for a comfortable stay while enjoying the beautiful Tuscan landscape. Many properties also include additional conveniences like Wi-Fi and parking, suiting the needs of families or groups.The charming countryside surrounding Sinalunga provides ample opportunities for outdoor activities with pets, including scenic walks through vineyards and olive groves. The nearby Val di Chiana is renowned for its picturesque views and tranquil atmosphere, making it ideal for leisurely strolls with your furry companions.
Are there any remote work holiday rentals in Sinalunga?
In Sinalunga, Tuscany, there are numerous remote work holiday rentals available, with around 228 options for travellers seeking a blend of work and leisure. This charming town offers a picturesque setting, rich in history and surrounded by the stunning Tuscan landscape. Many properties feature essential amenities for remote workers, including reliable internet access, free Wi-Fi in rooms, and dedicated office spaces, allowing for a productive work environment.Staying in Sinalunga, visitors can enjoy the local culture, with quaint shops and traditional Italian eateries nearby. The area is also well-situated for exploring the wider region, with attractions such as the beautiful Val di Chiana and historic towns like Montepulciano and Pienza just a short drive away. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sinalunga?
In Sinalunga, popular rental amenities include kitchens, which allow guests to prepare their own meals using fresh local produce. Many properties feature fireplaces, providing a warm and inviting atmosphere, particularly during the cooler months. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, gardens are a frequent amenity, offering outdoor spaces for relaxation and enjoying the beautiful Tuscan surroundings. Many rentals also come equipped with coffee and tea makers, ensuring that guests can enjoy their morning brews in comfort.
When is the best time to visit Sinalunga for a holiday rental?
July marks the peak season in Sinalunga, drawing travellers keen to experience the enchanting beauty of Tuscany. This month, along with August and September, is characterised by warm weather, ideal for exploring the picturesque landscapes and enjoying outdoor activities such as hiking and vineyard tours. The temperatures typically hover around 25 to 30 degrees Celsius, creating a ideal setting for leisurely strolls through the charming streets and indulging in the local cuisine.Visitors during peak season can take part in vibrant cultural events and festivals that celebrate the region's rich heritage, making it an exciting time to visit. Given the lively option, July is particularly popular among those seeking a vibrant holiday experience filled with both adventure and relaxation.For those looking for a more budget-friendly option, consider planning your trip in December. While this month is quieter, it offers a unique charm with fewer tourists and the opportunity to experience authentic Tuscan winter festivities. The cooler temperatures, ranging from 0 to 10 degrees Celsius, mean you can enjoy cosy evenings in local restaurants, savouring hearty dishes and fine wines.
What are the top attractions in Sinalunga?
In Sinalunga, Tuscany, visitors can engage in the region's rich culture and stunning landscapes. The historic town centre features charming medieval architecture, with top sites such as the Church of San Bartolomeo and the picturesque Piazza della Repubblica, where local markets often take place.For those interested in exploring the surrounding countryside, the beautiful Val di Chiana offers breathtaking views and opportunities for hiking or cycling through vineyards and olive groves. Just a short drive away, the enchanting town of Montepulciano is renowned for its wine and Renaissance architecture, making it a superb day trip from Sinalunga.Additionally, the nearby village of Trequanda, with its quaint streets and panoramic vistas, provides a lovely setting for leisurely strolls and photography.
Are all fees included in the Sinalunga 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 Sinalunga holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sinalunga 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 Sinalunga holiday homes?
You can find great discounts on holiday homes in Sinalunga 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 Sinalunga holiday home booking on Stayz?
To find Sinalunga 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 Sinalunga?
A long-stay holiday home in Sinalunga 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 Sinalunga holiday home?
Book your Sinalunga 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 Sinalunga?
Prices for holiday homes in Sinalunga 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 Sinalunga 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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