Siena holiday lettings

We found 2,163 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Siena by choosing from 39 houses, 246 apartments and other holiday rentals. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be 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 - Siena

Showing deals for:12 Jun - 19 Jun

Image gallery for PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Pool
10 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)

PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Castelnuovo Berardenga

9% off
Price is £4,836
for 7 nights, 1 villa
£691 per night
includes taxes & fees
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Why visit Siena

  • Historic architecture: Explore the stunning Siena Cathedral and other historic palaces that showcase the city's rich heritage.
  • Charming streets: Stroll through picturesque streets lined with outdoor cafés, perfect for relaxation and people-watching.
  • Cultural immersion: Engage with Siena's vibrant culture through local festivals and artistic events that reflect its unique charm.
  • Scenic landscapes: Enjoy the breathtaking views of the Tuscan countryside that surrounds this enchanting city.
  • Diverse accommodation: Choose from luxurious villas to cosy apartments for a comfortable stay tailored to your needs.

Popular types of accommodation in Siena

Discover the charm of Siena with our selection of holiday rentals. Whether you prefer a luxurious villa, a cosy private vacation home, or a stylish apartment, we have the perfect accommodation to suit your needs. Explore the stunning architecture and rich history of this iconic city while enjoying the comfort and convenience of our Siena holiday rentals. Your ideal getaway awaits—find your perfect retreat in rentals Siena today!

  • Villas: The top choice for holiday rentals in Siena, offering luxurious space and stunning views perfect for relaxation.
  • Houses: A popular option, ideal for families or groups seeking comfort and privacy during their stay.
  • Apartments: A convenient choice for those wanting to immerse themselves in local culture while enjoying modern amenities.
  • Caravan Parks: A unique and adventurous way to experience Siena, perfect for nature lovers and those seeking a more laid-back atmosphere.
  • Cottages: Charming and quaint, these are perfect for a cosy getaway in the beautiful Tuscan countryside.**

Top attractions in Siena

Siena, Tuscany, is perfect for culture enthusiasts and romantic getaways, featuring stunning churches, historic palaces, and vibrant piazzas. Notable attractions include the magnificent Siena Cathedral, which showcases the city's rich heritage. With a variety of experiences catering to families and culture seekers alike, visitors can immerse themselves in Siena's unique charm and history, ensuring a memorable vacation in this enchanting Italian city.

  • Siena Cathedral: A magnificent example of Italian Gothic architecture, this cathedral features stunning frescoes and intricate marble floors. Its striking façade and the impressive interior create a rich cultural experience that reflects Siena's artistic heritage.
  • Piazza del Campo: Renowned for its unique shell shape, this bustling square is the heart of Siena, hosting the famous Palio horse race. Surrounded by historic buildings, it's a vibrant gathering place filled with cafes and a lively atmosphere.
  • Fortezza Medicea: This historic fortress offers panoramic views of Siena and its surroundings. Built in the 16th century, it showcases Renaissance military architecture and provides a tranquil space for leisurely walks amidst gardens.

Things to do recommended for couples

For a romantic getaway in Siena, visit the enchanting Castle of Brolio for wine tasting, savour a meal at Frateria di Padre Eligio for a delightful dining experience, and unwind at San Giovanni Terme Rapolano for a soothing spa treatment. Perfect for couples seeking romance and relaxation!

Things to do recommended for families

Your family can enjoy the thrilling atmosphere at Stadio Artemio Franchi, experience adventurous karting at Siena Circuit, or gaze at the stars at Chianti Observatory. Each location offers unique vibes for a memorable family holiday in Siena.

Things to do recommended for groups

Groups visiting Siena can indulge in exquisite wines at Enoteca Italiana, enjoy captivating performances at Teatro dei Rinnovati, and embark on an adventurous hike with stunning scenery at Hedonistic Hiking, located a mere 5.6km from the city.

What do I need to keep in mind when booking a vacation in 'Siena

If you're travelling with a group, family, pets, or seeking extended stays, be sure to refine your search according to your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Siena with a group: Think about how many bedrooms you require, as well as any additional features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Siena with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Siena: For many, a family holiday isn't truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Siena: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Siena

Siena, a jewel of Tuscany, offers a rich tapestry of culture and history for the discerning traveller. Stroll through its charming streets, relax in outdoor cafés, and immerse yourself in the stunning landscapes that surround the city. With a vibe that is both welcoming and serene, Siena is perfect for a romantic getaway or a peaceful holiday. Don't miss the heart of Siena, where historical treasures await your exploration, making it an unforgettable vacation destination.

  • Castellina in Chianti: Nestled approximately 6.8km from Siena, Castellina in Chianti captivates visitors with its romantic charm and stunning landscapes. This delightful city is renowned for its outdoor experiences, making it an ideal destination for nature lovers. Enjoy a range of activities such as rejuvenating spa treatments and leisurely walks through the scenic countryside. The area is dotted with historic landmarks, including castles and ancient sites, offering a glimpse into its rich heritage. Whether you’re indulging in fine wine or exploring the local culture, Castellina in Chianti promises an enchanting escape.
  • Siena City Centre: The heart of Siena, this vibrant neighbourhood is steeped in culture and history. Located in close proximity to many of the city’s iconic sites, Siena City Centre is perfect for families and culture enthusiasts alike. Visitors can immerse themselves in the local scene with a variety of educational experiences and wellness options, including popular spa and body treatment venues. Iconic landmarks such as historic buildings and tourist precincts highlight the area’s artistic heritage, making it a must-visit for anyone wishing to experience the essence of Siena.
  • Castelnuovo Berardenga: Just 5.6km from Siena, Castelnuovo Berardenga is a charming city that offers a blend of romance and entertainment. With its picturesque landscapes and outdoor activities, it’s ideal for those seeking both relaxation and excitement. The city boasts a vibrant theatre scene and numerous spa options for unwinding after a day of exploration. Visitors can marvel at historic places and monuments within the area, enriching their understanding of local history while enjoying the stunning Tuscan scenery. Castelnuovo Berardenga is a delightful destination for a memorable getaway.

Best time to go to Siena

If you're planning a trip to Siena, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageSlightly Low
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly area where you can plan new journeys, continue from where you last stopped, or manage your travel arrangements. You'll discover your saved or booked properties neatly organised into Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical area of Siena awaits your stay

Come and experience Siena and its cathedral, history and monuments. Renowned for its museums, local tours and cafes, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Siena

Are you searching for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Siena a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Siena Circuit (7.2 mi / 11.5 km)
  • Cantalici Winery (10.6 mi / 17.1 km)
  • Castello di Radda Winery (12.5 mi / 20.1 km)
  • Villa a Sesta Polo Club (12.6 mi / 20.3 km)
  • San Giovanni Terme Rapolano (13.3 mi / 21.4 km)
  • Badia a Coltibuono (13.5 mi / 21.8 km)

Exploring the natural landscape of Siena

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Siena is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Chianti Sculpture Park (5.7 mi / 9.2 km)
  • Val di Merse (11.2 mi / 18 km)
  • Sentierelsa Trail (12.4 mi / 20 km)
  • Terme Antica Querciolaia (13.9 mi / 22.4 km)
  • I Canaloni del Torrente Farma (17.6 mi / 28.3 km)
  • Val di Chiana (29.5 mi / 47.4 km)

Transport options to and around Siena

The nearest airport is in Peretola Airport (FLR), located 34.1 mi (54.8 km) from the city centre.

If you prefer train travel, you can make your way to Siena Station.

Frequently asked questions

What is the best area to stay in Siena when booking a holiday rental?
When considering the best area to stay in Siena, Tuscany, you might want to explore the historic centre, which is a UNESCO World Heritage site and brimming with charm. This area offers a range of holiday rentals, from rustic apartments to elegant villas, allowing you to immerse yourself in the city's rich culture and history. One of the top attractions nearby is the stunning Piazza del Campo, renowned for its unique shell shape and vibrant setting, especially during the Palio horse race. Additionally, you can visit the magnificent Siena Cathedral, a masterpiece of Gothic architecture that captivates visitors with its intricate façade and beautiful interiors.

Another delightful area to consider is the neighbourhood surrounding the Sant'Agostino district, known for its tranquil streets and local charm. This area is slightly less touristy, providing a more authentic experience while still being within walking distance of key attractions. Here, you can enjoy local eateries and quaint shops, making it an ideal spot for those wanting to experience the everyday life of Siena.
How much does it cost to rent a holiday home in Siena?
Prices for holiday rentals in Siena 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 Siena 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 Siena holiday house rentals?
You can find great discounts on house rentals in Siena 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 Siena?
In Siena, apartments are the most popular type of holiday rental, with around 1,200 available throughout the city. These apartments are often situated in charming neighbourhoods, close to historic sites such as the Piazza del Campo and the stunning Siena Cathedral. Most units come equipped with fully functional kitchens, inviting living areas, and many feature balconies or terraces that offer lovely views of the Tuscan landscape.

For those seeking more space, there are approximately 180 holiday houses and 176 villas, which cater well to families or larger groups. These properties typically include multiple bedrooms, private gardens, and outdoor seating areas, making them ideal for relaxation after a day of exploring the region's rich history and culture.
Are there any family house rentals in Siena?
In Siena, Tuscany, there is a wealth of family-friendly house rentals available—specifically, around 217 properties scattered throughout the city and its surrounding areas. Visitors can explore charming neighbourhoods such as the historic centre, where many homes retain traditional Tuscan architecture and provide spacious living areas, making them ideal for families. Many of these residences come equipped with full kitchens, allowing for easy meal preparation, and some even feature outdoor spaces like gardens or terraces where children can play.

Additionally, the proximity to top attractions such as the Piazza del Campo and the stunning Siena Cathedral offers families a wonderful opportunity to immerse themselves in the local culture and history. Many properties are also close to local markets, where families can sample authentic Tuscan cuisine and fresh produce.
Can I rent a holiday home with a pool or hot tub in Siena?
In Siena, Tuscany, there are many holiday homes available for rent that feature pools, with around 67 options to choose from. This enchanting city is surrounded by the beautiful Tuscan countryside, making it an ideal location for those seeking relaxation and stunning views. Properties with pools can typically be found in the scenic hills just outside the city, where guests can enjoy the tranquillity of rural living while being a short drive from Siena's historic centre.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, outdoor dining areas, and fully equipped kitchens, allowing for comfortable self-catering during their stay. Many homes also feature spacious gardens, sun loungers, and sometimes even hot tubs, superb for unwinding after a day of exploring the rich history and culture of Siena. Find your rental in Siena with a pool or a hot tub.
Can I find long-stay holiday rentals in Siena?
A long-stay holiday rental in Siena 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 Siena?
In Siena, there are numerous pet-friendly house rentals available, with around 129 options for travellers seeking accommodation that welcomes their furry companions. The city itself is steeped in history and charm, offering a variety of holiday rentals that range from traditional Tuscan villas to modern apartments. Many of these properties come equipped with amenities such as spacious gardens, terraces, and fully equipped kitchens, great for families or groups looking to enjoy a comfortable stay.

The historic centre of Siena is a UNESCO World Heritage site, featuring beautiful streets and piazzas that are ideal for leisurely strolls with pets. Additionally, nearby parks and green spaces, such as the Orto de' Pecci, provide lovely spots for walks and relaxation. This area is particularly known for its stunning views and tranquil atmosphere, making it a great choice for those travelling with pets.
Are there any remote work holiday rentals in Siena?
In Siena, Tuscany, there are ample remote work holiday rentals available, with around 1,236 options for travellers. This historic city, renowned for its medieval architecture and vibrant culture, is an excellent choice for those looking to combine work and leisure. Many properties come equipped with essential amenities for remote work, including high-speed internet, Wi-Fi access in rooms, and dedicated workspace areas or desks.

As you explore Siena, you'll find that numerous rentals are situated near key points of interest, such as the stunning Piazza del Campo and the magnificent Siena Cathedral. These locations not only provide a rich cultural experience but also offer nearby cafés and restaurants where you can take breaks or enjoy meals. Additionally, many rentals feature comfortable living spaces, kitchens for self-catering, and some even have outdoor terraces or gardens, allowing for a pleasant work-life balance in an inspiring setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Siena holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Siena 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 Siena?
In Siena, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy local produce. Many rentals also feature coffee and tea makers, superb for starting the day with a warm beverage. Onsite parking is a significant advantage, particularly in the historic centre where space can be limited. Additionally, several properties are pet-friendly, welcoming travellers who wish to bring their furry companions along. Many rentals are conveniently located near museums, enabling guests to easily explore the rich cultural heritage of Siena.
When is the best time to visit Siena for a holiday rental?
April is the most popular month to visit Siena, as the springtime brings mild weather and blooming landscapes, superb for exploring this historic city. During this time, you can enjoy comfortable temperatures ranging from 10 to 20 degrees Celsius, making it ideal for leisurely strolls through the picturesque streets, visiting iconic sites like the Piazza del Campo, and indulging in local cuisine at outdoor cafés.

The peak tourist season in Siena spans from July to September, attracting visitors eager to experience the famous Palio horse race and the vibrant summer atmosphere. While this period offers a lively buzz and a plethora of events, it can also mean larger crowds and higher accommodation prices.

For those looking for a more budget-friendly option, November presents a wonderful opportunity to explore Siena without the hustle and bustle. The cooler temperatures, ranging from 5 to 15 degrees Celsius, create a ideal setting for enjoying the city's rich history and art without the distractions of peak tourism. Plus, the autumn colours add a unique charm to the cobblestone streets and historic buildings.

Ultimately, the best time to book a holiday rental in Siena depends on your preferences: whether you're drawn to the vibrant energy of the summer months or the peaceful beauty of spring and autumn.
How early should I book a Siena holiday rental?
Book your Siena 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 Siena?
In Siena, visitors can experience firsthand a rich tapestry of history and culture. The historic centre, a UNESCO World Heritage Site, is home to the striking Piazza del Campo, famous for its unique shell shape and the annual Palio horse race. The surrounding narrow streets are filled with charming shops and cafes, superb for enjoying local Tuscan cuisine.

Another highlight is the majestic Siena Cathedral, or Duomo di Siena, showcasing stunning Gothic architecture and intricate artworks, including works by Michelangelo. Nearby, the Museo dell'Opera del Duomo offers further insights into the cathedral's history and art.

For those interested in art, the Pinacoteca Nazionale di Siena houses an impressive collection of Sienese paintings. The neighbourhood of Contrada, with its vibrant setting and sense of community, is also worth exploring, especially during the Palio season when its streets come alive with festivities.
Can I change or cancel my Siena home rental booking on Vrbo?
To find Siena 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 Siena 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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