Siena holiday homes

We found 1,982 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Siena by choosing from 41 houses, 227 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:15 Jan - 22 Jan

Interior
Outdoor dining
Interior
Exterior
Exceptional
(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

5% off
NZ$25,205
for 7 nights, 1 villa
NZ$3,601 per night
includes taxes & fees
Villa Curiano - Siena
Property grounds
Terrace/patio
Room
Exterior
Exceptional
(60 reviews)

Apartment in Farmhouse 3 Km far from the center of Siena for 4 people

Siena

9% off
NZ$2,866
for 7 nights, 1 home
NZ$409 per night
includes taxes & fees
Apartment in Farmhouse 3 Km far from the center of Siena for 4 people
Interior
Property grounds
Interior
Interior
Exceptional
(47 reviews)

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Castelnuovo Berardenga

9% off
NZ$5,065
for 7 nights, 1 villa
NZ$724 per night
includes taxes & fees
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills
Interior
Outdoor dining
Property grounds
Room
Exceptional
(10 reviews)

Apartment in renovated farmhouse in typical Chianti Tuscan village

Castelnuovo Berardenga

7% off
NZ$2,192
for 7 nights, 1 home
NZ$313 per night
includes taxes & fees
Apartment in renovated farmhouse in typical Chianti Tuscan village
Dining
Dining
Living room
Room
Exceptional
(31 reviews)

Palazzo Pannilini-Historical residence

Siena

7% off
NZ$10,499
for 7 nights, 1 apartment
NZ$1,500 per night
includes taxes & fees
Palazzo Pannilini-Historical residence
Living area
Pool
Exterior
Property grounds
Exceptional
(21 reviews)

Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm

Siena

5% off
NZ$2,644
for 7 nights, 1 home
NZ$378 per night
includes taxes & fees
Borgo dei Fondi / Il Forno – Ground Floor/ Modern Comfort and Tuscan Charm
Property grounds
Terrace/patio
Pool
Property grounds
Exceptional
(118 reviews)

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena

14% off
NZ$9,329
for 7 nights, 1 villa
NZ$1,333 per night
includes taxes & fees
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
Living area
Property grounds
Private kitchen
Exterior
Exceptional
(17 reviews)

Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena

Siena

9% off
NZ$10,877
for 7 nights, 1 home
NZ$1,554 per night
includes taxes & fees
Beautiful farmhouse nestled in very sweet hills just a few minutes from Siena
Property grounds
Property grounds
Pool
Interior
Exceptional
(82 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
NZ$1,114
for 7 nights, 1 home
NZ$159 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Outdoor dining
Pool
Pool
Pool
Exceptional
(29 reviews)

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena

14% off
NZ$5,264
for 7 nights, 1 villa
NZ$752 per night
includes taxes & fees
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Interior
Exterior detail
Interior
Terrace/patio
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

14% off
NZ$2,366
for 7 nights, 1 home
NZ$338 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
Interior
Outdoor dining
Dining
Room
Exceptional
(46 reviews)

Period residence located in the heart of Siena

Siena

5% off
NZ$1,875
for 7 nights, 1 apartment
NZ$268 per night
includes taxes & fees
Period residence located in the heart of Siena
Living area
Room
Bathroom
Dining
Exceptional
(15 reviews)

Il Casato, beautiful apartment in the heart of Siena

Siena

11% off
NZ$2,084
for 7 nights, 1 apartment
NZ$298 per night
includes taxes & fees
Il Casato, beautiful apartment in the heart of Siena

  • 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

Why visit Siena

  • Historic Architecture: Wander through Siena’s ancient streets lined with stunning churches, palazzos, and timeless piazzas.
  • Cultural Heritage: Immerse yourself in Siena’s rich past showcased by its historical landmarks and vibrant local traditions.
  • Scenic Beauty: Enjoy leisurely strolls in picturesque corners that reveal the enchanting blend of nature and history.
  • Family-Friendly Charm: Experience a welcoming atmosphere perfect for cultural outings and relaxed family adventures.
  • Romantic Vibes: Discover hidden gems and tranquil spots ideal for a romantic walk through Siena’s storied lanes.

Top attractions in Siena

Siena in Tuscany, Italy beckons visitors with its rich cultural heritage and stunning outdoor settings. Explore its historic churches, palatial landmarks, and charming piazzas that offer a perfect mix of city and family experiences. Whether you’re seeking a culturally immersive day out, a romantic walk, or a family adventure, Siena provides an enchanting setting that captures the essence of Italian tradition and beauty.

  • Piazza del Campo: Experience Siena’s vibrant heart at this historic piazza, renowned for its unique shell shape and lively atmosphere, perfect for soaking up the local culture.
  • Porta Camollia: Step through time at this ancient gate arch, offering a glimpse of Siena’s storied past and cultural heritage.
  • Torre del Mangia: Climb the clock tower for panoramic city views, a striking symbol of Siena’s medieval splendour and urban charm.

Things to do recommended for couples

Explore Siena's enchanting streets hand-in-hand, savour local Tuscan cuisine, and enjoy a serene sunset at the iconic Piazza del Campo. Perfect for a Kiwi couple seeking authentic Italian romance.

Things to do recommended for families

Families exploring Siena can wander through medieval streets, enjoy gelato at local cafes, and participate in hands-on cooking classes. Discover the charm of Tuscany with interactive museum visits and outdoor picnics, perfect for creating memorable adventures in the heart of Italy.

Things to do recommended for groups

Experience the thrill of ziplining and navigating ropes courses at Saltalbero Adventure Park, located 21km from Siena. This outdoor adventure offers an exhilarating way for your group to bond while enjoying the beautiful Tuscan countryside.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you're journeying with a group, travelling as a family, bringing your pets along, or seeking extended stays, be sure to use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Siena with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or an outdoor area for gathering with friends. Luckily, you can use filters on Vrbo to find all these options and more.
  • Traveling to Siena with young kids: Traveling with young children can be challenging. You need to ensure their comfort and safety, as well as age-appropriate amenities, such as private swimming pool. It’s also a good idea to consider your proximity to family-friendly attractions.
  • Taking your pets with you to Siena: For many, a family journey is not complete without their four-legged mate tagging along. If that sounds like you, then have a gander at Vrbo properties that are pet-friendly. Most pet-welcoming places offer feeding bowls and cosy beds, ensuring every member of the family feels right at home.
  • Planning for a long term stay visiting Siena: If you're seeking holiday rentals with long-term deals, you've come to the right spot. Use the appropriate filter to quickly locate and save on monthly stays. You may also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Siena

Discover the heart of Siena, where historical charm meets a relaxed, friendly atmosphere. Stroll through ancient streets, explore hidden corners, and enjoy the scenic beauty of this secluded city. Experience culture and romance in a place that truly embodies the essence of hidden Italy. Whether on a leisurely day trip or an immersive holiday, Siena’s rich past and vibrant vibes offer an unforgettable journey in the heart of Tuscany.

  • Radda in Chianti: Nestled 19km from Siena, Radda in Chianti offers a charming mix of history and modern recreation. The city is renowned for its romantic ambience and outdoor pursuits. Visitors can enjoy rejuvenating spa and body treatment facilities, as well as a round of golf amid scenic countryside views. Rich in cultural heritage, the area is dotted with historic landmarks, a castle, and notable monuments, providing a perfect blend of relaxation and exploration.
  • Castellina in Chianti: Located 18km from Siena, Castellina in Chianti charms travellers with its romantic and entertainment-themed attractions. This city boasts a variety of leisure activities including therapeutic spa treatments, body care, and engaging theatre experiences. The surroundings are steeped in history, featuring a historic site, a castle, and monuments that evoke the rich past of the region. The blend of outdoor adventures and cultural exploration makes it an appealing destination.
  • Siena City Centre: At the heart of Siena, the city centre is a vibrant neighbourhood that offers a dynamic mix of cultural and outdoor experiences. The area is celebrated for its rich historical tapestry, featuring iconic piazzas, a stunning cathedral, and traditional squares. Beyond its cultural allure, visitors can explore local spa facilities, educational experiences, and body treatments. The lively streets and historic charm provide a quintessential Italian city experience with a distinct Tuscan flavour.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.8°F (4.9°C)Light RainMostly SunnyAverage
February42.8°F (6.0°C)Light RainMostly SunnyAverage
March47.5°F (8.6°C)Light RainMostly SunnyAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly High
May60.4°F (15.8°C)Light RainMostly SunnyAverage
June69.8°F (21.0°C)Light RainSunnyAverage
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly High
October58.5°F (14.7°C)Light RainMostly SunnySlightly Low
November50.0°F (10.0°C)Light RainMostly SunnySlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Looking to cut costs on your upcoming journey? Being flexible with your travel dates can really pay off, as prices often fluctuate. You might also enjoy considerable savings by planning a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to narrow down your choices by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are neatly organised into categories: Potential, Upcoming, and Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/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:

  • Val di Merse (11.2 mi / 18 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)
  • Chianti Sculpture Park (5.7 mi / 9.2 km)
  • Alta Val d'Elsa River Park (11.1 mi / 17.8 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Siena holiday homes prices shown on Bookabach?
Bookabach 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 Siena holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 Siena holiday homes?
You can find great discounts on holiday homes in Siena on Bookabach, 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 Siena holiday home booking on Bookabach?
To find Siena holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Siena?
A long-stay holiday home 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 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 Bookabach?
Bookabach'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 Siena holiday home?
Book your Siena 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Siena?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Siena to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas