Siena vacation rentals

We found 2,161 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Siena by choosing from 41 houses, 243 apartments, and other vacation rentals. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, such as parking and air conditioning. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Siena

Showing deals for:Jun 19 - Jun 26

Image gallery for FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

Private swimming pool with breathtaking views over the typical Tuscan landscape
9.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)

FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

Castellina in Chianti

9% off
Price is $1,589
$11,122 for 7 nights
All fees included
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!

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Find out more about Siena

Why visit Siena

  • Magnificent Siena Cathedral: A stunning architectural masterpiece that showcases breathtaking artistry and history.
  • Piazza del Campo: The heart of Siena, this vibrant square hosts events and offers a lively atmosphere.
  • Charming Countryside: Explore the picturesque Sienese countryside, including the famous Chianti region.
  • Rich Local Culture: Immerse yourself in Siena's rich heritage through its historic palaces and traditions.
  • Diverse Accommodations: Choose from charming villas, cozy apartments, and luxurious stays for a perfect getaway.

Popular types of accommodation in Siena

Planning a getaway to Siena? You're in the right place. Our platform offers a variety of vacation rentals to suit every traveler's needs. Discover charming villas, houses, and cozy apartments that provide the perfect home base for exploring this stunning city. Whether you're looking for a luxurious villa or comfortable hotel rooms in Siena, we have options that promise transparency, savings, and reassurance for your stay.

  • Villas: The top choice for vacation rentals in Siena, these spacious and luxurious homes offer stunning views and private amenities for a perfect getaway.
  • Houses: A favorite among travelers, these homes provide a comfortable and personalized experience for families and groups.
  • Apartments: Ideal for those seeking convenience, these units allow you to enjoy the local lifestyle while being close to attractions.
  • Caravan Parks: For a unique experience, these parks offer a fun and social atmosphere with facilities for campers and RVs.
  • Cottages: Charming and cozy, these quaint accommodations are perfect for a romantic escape or a peaceful retreat.**

Top attractions in Siena

Siena, Tuscany, is perfect for a culture-filled, romantic getaway. Explore stunning churches, historic palaces, and vibrant piazzas while immersing yourself in the local culture. Don't miss the magnificent Siena Cathedral and take a scenic trip through the picturesque Sienese countryside. With plenty of attractions and sightseeing opportunities, Siena offers a delightful experience for families and travelers alike. Enjoy your adventure in this charming Italian city.

  • Piazza del Campo: This iconic square is the heart of Siena, known for its unique shell shape and vibrant atmosphere. It's a gathering place for locals and visitors alike, surrounded by historic buildings and cafes, making it perfect for people-watching and soaking in the culture.
  • Fortezza Medicea: A historic fortress offering a glimpse into Siena's past. Its massive walls and scenic views create a peaceful retreat amidst the city hustle, with cultural events often held in its grounds.
  • Siena Cathedral: A stunning example of Gothic architecture, this cathedral boasts intricate marble floors and breathtaking frescoes. Visitors can explore its rich history and artistic treasures, making it a must-see for culture enthusiasts.

Things to do recommended for couples

Ready for a romantic getaway in Siena? Don't miss a visit to the Villa a Sesta Polo Club, just 13 miles away. Experience luxury vibes while enjoying the beautiful Tuscan countryside, perfect for couples looking to unwind and create lasting memories together.

Things to do recommended for families

Your family will love exploring the historic Piazza del Campo, where kids can run around and enjoy gelato. Visit the Siena Cathedral for its stunning architecture, or take a family-friendly cooking class to learn how to make authentic Italian pasta together.

Things to do recommended for groups

Groups in Siena can immerse themselves in local culture by enjoying a traditional Tuscan cooking class, exploring the historic Piazza del Campo, and taking a guided tour of the magnificent Siena Cathedral. Don't miss a wine tasting in the scenic Chianti countryside for a true taste of Tuscany.

*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

When traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences when filtering your options. 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 amenities you might want, like a full kitchen or outdoor area for group activities. Luckily, you can easily filter for all of these options, and more, on Vrbo.
  • Traveling to Siena with young kids: Traveling with young kids can be quite a task. It's essential to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siena: For many families, a vacation isn't truly enjoyable without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Siena: If you're searching for vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Siena

Experience the enchanting charm of Siena, a city steeped in history and culture, perfect for romantic getaways and outdoor adventures. Explore the stunning countryside surrounding Siena, including the picturesque Chianti area, renowned for its breathtaking scenery and friendly locals. Whether you choose to stay in the heart of Siena or venture into the tranquil provinces nearby, you're sure to enjoy a memorable vacation filled with rich heritage and serene landscapes.

  • Castellina in Chianti: Nestled 11 miles from Siena, Castellina in Chianti is a charming city known for its romantic atmosphere and outdoor adventures. This picturesque destination offers a variety of entertainment options, including spas and theaters, perfect for a relaxing getaway. Stroll through the historic streets, where you'll encounter stunning castles and monuments that tell the rich story of the region. Whether you're indulging in a spa treatment or enjoying a scenic hike through the vineyards, Castellina in Chianti provides a delightful blend of culture and nature.
  • Siena City Centre: The vibrant heart of Siena, the City Centre is a cultural hub that invites exploration. Surrounded by historic architecture, the area offers an abundance of outdoor experiences, from visiting the iconic Piazza del Campo to admiring the breathtaking Siena Cathedral. Travelers can enjoy spas and educational venues, making it a perfect spot for those seeking both relaxation and enrichment. The lively atmosphere, rich heritage, and picturesque squares make Siena City Centre a must-visit for anyone looking to immerse themselves in Tuscan culture.
  • Castelnuovo Berardenga: Located 9 miles from Siena, Castelnuovo Berardenga is a delightful city that captivates visitors with its romantic charm and outdoor activities. The area is perfect for those seeking entertainment, featuring luxurious spas and beautiful outdoor spaces to explore. You can wander through historic sites, including impressive castles and monuments that reflect the area's storied past. With its welcoming ambiance and stunning landscapes, Castelnuovo Berardenga offers an enchanting escape for tourists eager to experience the best of Tuscany.

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 simple

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and accumulate OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient way to plan new trips, manage your existing plans, and keep track of your bookings. All the properties you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic 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 friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Siena

Are you looking for attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Siena a fun place to get away. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Siena. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Chianti Sculpture Park (5.7 mi / 9.2 km)
  • Hedonistic Hiking (9.4 mi / 15.1 km)

Transportation options to and around Siena

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

If you're traveling by train, you can make your way to Siena Station.

Frequently asked questions

What is the best area to stay in Siena, Tuscany, Italy when booking a vacation rental?
When considering the best area to stay in Siena, Tuscany, for a vacation rental, the historic center is an exceptional choice. This area is renowned for its medieval architecture and vibrant setting, making it a great base for exploring the city. You can easily visit iconic attractions such as the stunning Piazza del Campo, known for its unique shell shape and lively events, including the famous Palio horse race. Another must-see is the magnificent Siena Cathedral, an architectural masterpiece that showcases the city's rich history and artistry.

In the historic center, you'll find a variety of charming vacation rentals, from quaint apartments to luxurious accommodations, all within walking distance of local shops, restaurants, and cultural sites. The convenience of being in the heart of Siena allows you to immerse yourself in the local culture and enjoy the delightful Tuscan cuisine at nearby eateries.
How much does it cost to rent a vacation home in Siena?
Prices for vacation 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 vacation 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 vacation rental accomodation in Siena?
In Siena, apartments are the most popular type of vacation rental, with around 300 options available throughout the city. These rentals are typically situated in charming neighborhoods close to top attractions such as the Piazza del Campo and the Siena Cathedral. Most apartments feature essential amenities such as fully equipped kitchens, comfortable living areas, and some even provide balconies or terraces to enjoy the stunning Tuscan views.

For travelers seeking more space, there are about 45 vacation houses and 44 villas available, which are superb for families or larger groups. These properties often come with multiple bedrooms, private gardens, and outdoor seating areas, allowing guests to relax and gather together. Additionally, there are several cottages and campsites, offering even more variety for those looking to experience the picturesque countryside around Siena.
Are there any family house rentals in Siena?
In Siena, Tuscany, there are numerous family-friendly vacation rentals available, with around 217 options to choose from. The city is rich in history and culture, making it an ideal spot for families looking to explore. Many properties are located in and around the historic center, featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor terraces or gardens superb for children to play or for family gatherings.

Visitors can easily reach nearby attractions such as the iconic Piazza del Campo and the stunning Siena Cathedral, both of which offer opportunities for family outings and cultural experiences. Additionally, some rentals provide amenities such as Wi-Fi, air conditioning, and even private pools, enhancing comfort during your stay.
Can I rent a vacation home with a pool or hot tub in Siena?
In Siena, Tuscany, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 67 options to choose from. This historic city and its surrounding countryside offer a beautiful backdrop for a relaxing getaway. Many of these properties come with private pools, hot tubs, and stunning views of the Tuscan landscape, making them superb for unwinding after a day of exploring.

Travelers can expect a range of amenities, including spacious living areas, fully equipped kitchens, and outdoor dining spaces where they can enjoy meals al fresco. Some rentals may also feature gardens, barbecue facilities, and proximity to local vineyards or charming villages, enhancing the overall experience of the Tuscan lifestyle.
Can I find long-stay vacation rentals in Siena?
A long-stay vacation rental in Siena is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Siena?
In Siena, travelers will find a significant selection of pet-friendly house rentals, with around 129 options available. Many of these properties are situated within the historic city center, offering easy access to the stunning Piazza del Campo and the iconic Siena Cathedral. The rentals typically feature amenities such as fully equipped kitchens, cozy living spaces, and outdoor areas where pets can roam and relax.

Additionally, the surrounding Tuscan countryside provides beautiful landscapes for walks with pets, with opportunities to explore nearby vineyards and olive groves. Travelers can also enjoy local parks and green spaces, making it a great destination for those looking to vacation with their furry friends.
Are there any remote work vacation rentals in Siena?
In Siena, Tuscany, remote work vacation rentals are plentiful, with around 309 options available for travelers seeking a work-friendly environment. Many of these properties come equipped with essential amenities such as high-speed internet, Wi-Fi in rooms, and dedicated workspaces or desks, making it convenient for those who need to balance work and leisure.

Travelers can expect a variety of accommodations, ranging from charming apartments in the historic center to more spacious villas on the outskirts, often featuring beautiful views of the Tuscan countryside. These rentals typically include comforts like fully equipped kitchens, cozy living areas, and access to outdoor spaces, providing an inclusive setting for relaxation after a day of work.

Staying in Siena also offers the advantage of being close to the city's rich history and culture, with landmarks like the Piazza del Campo and the Siena Cathedral just a short distance away. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Siena vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Siena with parking available—perfect for families or travelers 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 vacation rental amenities include kitchens, which allow travelers to prepare their own meals and enjoy the local cuisine at their convenience. Many rentals also feature coffee and tea makers, superb for those who appreciate a morning brew. Onsite parking is another appealing amenity, particularly for visitors who may be driving and want easy access to their vehicle. Additionally, some properties are pet-friendly, accommodating travelers who wish to bring their furry companions along. Many rentals are conveniently located near museums, making it easy for guests to explore the rich cultural heritage of Siena without having to travel far.
When is the best time to visit Siena for a vacation rental?
April is one of the best months to visit Siena, as it marks the beginning of spring and the city starts to come alive with vibrant colors and pleasant weather. During this time, you can enjoy outdoor activities like exploring the historic architecture and wandering through the charming streets without the overwhelming crowds typical of the summer peak season.

The peak tourist season in Siena runs from July to September, when visitors flock to experience the famous Palio horse race and the warm, sunny days superb for sightseeing. Temperatures during these months can soar into the mid-80s Fahrenheit, making it an ideal time for outdoor dining in the city's picturesque piazzas. However, if you prefer a more tranquil experience, April offers mild temperatures in the 50s to low 70s Fahrenheit, ideal for leisurely strolls and enjoying the local cuisine at outdoor cafes.

For those looking for a more budget-friendly option, consider visiting in November. While this month may be less popular, it offers a unique opportunity to experience Siena's authentic charm, with fewer tourists and a chance to appreciate the local culture at a slower pace.

Ultimately, whether you choose the lively option of the summer or the refreshing spring air of April, Siena promises rich experiences that cater to all types of travelers.
How early should I book a Siena vacation rental?
Book your Siena vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Siena, Tuscany, Italy?
In Siena, travelers can immerse themselves in a rich tapestry of history and culture. The iconic Piazza del Campo is a must-visit, famous for its unique shell shape and the Palio horse race, which takes place twice a year. Surrounding the square, you'll find charming vacation rentals that allow easy access to local cafes and shops.

The stunning Siena Cathedral, with its intricate façade and breathtaking interior, is another highlight. Nearby, the historic center offers narrow, winding streets filled with medieval architecture and local artisan boutiques.

For those interested in art, the Pinacoteca Nazionale di Siena showcases an impressive collection of medieval and Renaissance masterpieces. The area around the cathedral and the piazza is particularly rich in vacation rentals, providing visitors with a chance to experience the city's vibrant setting.
Can I change or cancel my Siena home rental booking on Vrbo?
To find Siena vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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