Poggibonsi holiday lettings

We found 1,547 holiday rentals — enter your dates for availability

Select from 42 houses, 85 apartments and other holiday rentals to find the perfect place for your stay in Poggibonsi. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, including air conditioning and Wi-Fi. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Poggibonsi

Showing deals for:14 Nov - 21 Nov

Image gallery for Exclusive panoramic villa with private pool between Florence and Siena.

Pool
10 out of 10 rating
Exceptional
(16 reviews)

Exclusive panoramic villa with private pool between Florence and Siena.

Certaldo, Toscana

9% off
Price is £18,808
£2,687 per night
includes taxes & fees
Exclusive panoramic villa with private pool between Florence and Siena.

Find spaces that suit your style

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Find out more about Poggibonsi

Find out more about Poggibonsi

Why people love visiting rustic Poggibonsi

Enjoy the wineries and other features of Poggibonsi. One of the city's many top draws is its seafood restaurants. 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.

Sightseeing in and around Poggibonsi

Are you searching for attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Poggibonsi a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Castello di Monsanto (2.6 mi / 4.2 km)
  • Castello della Paneretta (3.2 mi / 5.1 km)
  • Tenuta Torciano Winery (4.2 mi / 6.8 km)
  • Sovestro in Poggio Winery (4.5 mi / 7.3 km)
  • Isole e Olena Winery (5.1 mi / 8.2 km)
  • Casa Sola - Chianti Winery (5.4 mi / 8.7 km)

Exploring the natural landscape of Poggibonsi

Whether you're an adventurous traveller or just want to appreciate the scenery, Poggibonsi is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (3.4 mi / 5.5 km)
  • Alta Val d'Elsa River Park (5.8 mi / 9.3 km)
  • Chianti Sculpture Park (13 mi / 20.9 km)
  • Le Caldane Thermal Baths (5.6 mi / 9 km)
  • Enoteca Italiana (13.6 mi / 21.9 km)
  • Val di Merse (20.8 mi / 33.5 km)

How to get to and around Poggibonsi

The nearest airport is in Peretola Airport (FLR), located 23 mi (37 km) from the city centre.

If you prefer train travel, you can make your way to Poggibonsi-San Gimignano Station.

Frequently asked questions

What is the best area to stay in Poggibonsi when booking a holiday rental?
When considering a holiday rental in Poggibonsi, the historic centre is a popular area to stay. This charming neighbourhood is steeped in history and offers a vibrant atmosphere with its quaint streets and local shops. One of the top attractions here is the impressive Castle of Poggibonsi, which dates back to the 12th century and provides breathtaking views of the surrounding countryside. Additionally, the nearby Church of San Lorenzo showcases beautiful architecture and is a lovely spot to explore.

Another appealing area to consider is the vicinity of the Staggia Senese Castle. Staying near this landmark not only allows easy access to its stunning grounds but also places you within reach of scenic walking paths that lead you through the picturesque Tuscan landscape. This area typically features a good number of holiday rentals, making it convenient to find a property that suits your needs.
How much does it cost to rent a holiday home in Poggibonsi?
Prices for holiday rentals in Poggibonsi 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 Poggibonsi 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 Poggibonsi holiday house rentals?
You can find great discounts on house rentals in Poggibonsi 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 Poggibonsi?
In Poggibonsi, apartments are the most popular type of holiday rental, with around 76 available in charming neighbourhoods that provide easy access to local attractions such as the historic Piazza Cavour and the nearby San Gimignano. These apartments typically come with fully equipped kitchens, cosy living areas, and some may even feature balconies for enjoying the Tuscan scenery.
Are there any family house rentals in Poggibonsi?
In Poggibonsi, Tuscany, there are numerous family-friendly house rentals available, with around 96 options to choose from. This charming town serves as a fantastic base for families looking to explore the beautiful Tuscan countryside and its rich history. Many of these properties offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and enjoy the fresh air.

As you explore the area, you'll find that Poggibonsi is conveniently located near popular attractions such as the historic towns of San Gimignano and Certaldo, both just a short drive away. These nearby towns boast medieval architecture, enchanting streets, and local eateries great for family outings. Visitors can also enjoy the scenic landscapes of the Chianti region, ideal for outdoor activities like hiking and cycling.
Can I rent a holiday home with a pool or hot tub in Poggibonsi?
In Poggibonsi, Tuscany, there are plenty of holiday homes available for rent that feature pools or hot tubs, with approximately 123 options to choose from. This picturesque town, situated in the heart of Tuscany, offers a blend of natural beauty and historical charm. Many of the properties come with amenities such as private swimming pools, outdoor terraces, and barbecue areas, providing an ideal setting for relaxation and outdoor dining.
Can I find long-stay holiday rentals in Poggibonsi?
A long-stay holiday rental in Poggibonsi 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 Poggibonsi?
In Poggibonsi, Tuscany, there are numerous pet-friendly house rentals available, with around 81 options to choose from. Many of these properties are set in picturesque surroundings, often featuring traditional Tuscan architecture and modern amenities. Travellers can expect spacious living areas, fully equipped kitchens, and outdoor spaces such as gardens or terraces, superb for enjoying the beautiful Tuscan landscape.
Are there any remote work holiday rentals in Poggibonsi?
In Poggibonsi, Tuscany, there are numerous remote work holiday rentals available, with around 142 options to choose from. This charming town offers a blend of historical sights and modern conveniences, making it an ideal location for remote workers. Many of the properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Poggibonsi holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Poggibonsi 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 Poggibonsi?
In Poggibonsi, popular rental amenities typically include kitchens and refrigerators, allowing guests to prepare their own meals during their stay. Many properties also feature shared pools, providing a refreshing way to relax after a day of exploring the beautiful Tuscan landscapes. Additionally, free Wi-Fi is commonly available in the accommodations, enabling travellers to stay connected while enjoying their holiday.
When is the best time to visit Poggibonsi for a holiday rental?
April is the most popular month to visit Poggibonsi, as the landscape bursts into life and the charming Tuscan countryside showcases its vibrant colours. This time of year sees a delightful climate, with temperatures typically hovering around 15-20 degrees Celsius, great for outdoor exploration and leisurely strolls through the picturesque streets.

As the peak season runs from July to September, Poggibonsi attracts a bustling crowd of travellers drawn to its rich history, stunning architecture, and the surrounding vineyards. During these warmer months, you can enjoy sun-soaked days filled with sightseeing, wine-tasting, and indulging in the local cuisine.

For those seeking a more tranquil experience, November presents an excellent opportunity to visit. With fewer tourists around, you can appreciate the serene beauty of the region and enjoy the local culture at a leisurely pace. Plus, the autumn scenery is truly enchanting, with golden leaves adding a touch of magic to the landscape.
How early should I book a Poggibonsi holiday rental?
Book your Poggibonsi 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 Poggibonsi?
In Poggibonsi, Tuscany, visitors can discover a rich tapestry of historical and cultural attractions. The town is renowned for its medieval architecture, with the impressive Castello della Magione offering insights into its storied past. Nearby, the Church of San Lorenzo is a beautiful example of local religious architecture, often drawing the attention of history enthusiasts.

For those looking to explore the natural beauty of the region, the surrounding Chianti countryside provides stunning landscapes, great for hiking and wine tasting. The nearby town of San Gimignano, famous for its medieval towers and UNESCO World Heritage status, is just a short drive away and offers a vibrant atmosphere with local shops and eateries.
Can I change or cancel my Poggibonsi home rental booking on Vrbo?
To find Poggibonsi 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Poggibonsi 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.

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