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Holiday rentals in Poggibonsi

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Top-rated holiday rentals in Poggibonsi

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment
5 out of 5 average rating, 316 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favourite
A panoramic terrace is visible, featuring a small table set with a light purple tablecloth and dark chairs. The surrounding stone wall offers views of the landscape at sunset, highlighting rolling hills and distant towers.
Tower
4.94 out of 5 average rating, 126 reviews

Medieval Tower experience with Panoramic Rooftop

If you are looking for a memorable experience, this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage
4.98 out of 5 average rating, 204 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Top guest favourite
A bright and inviting bedroom features a spacious bed adorned with decorative pillows and neatly arranged linens. Nightstands with lamps flank either side, providing soft illumination. A floral artwork enhances the wall above the bed, while a wooden door adds a warm touch to the space.
Apartment
4.94 out of 5 average rating, 125 reviews

Gallery Apartment near Chianti

Confortevole e luminoso appartamento in centro di Poggibonsi a 150 mt dalla Clinica Siena Eye Laser e da tutti i servizi necessari. Ampio Parcheggio pubblico adiacente al palazzo. Posizione strategica per raggiungere le città d'arte come Firenze, Siena, San Gimignano, Volterra, Pisa ed i bellissimi borghi del Chianti. Gallery Apartment è dotato di tutti i confort e saprà accogliervi come a casa vostra. Potrete sedervi ai tavolini nelle 2 terrazze e bere un buon chianti o un caffè al mattino.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home
4.98 out of 5 average rating, 225 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home
4.95 out of 5 average rating, 189 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 206 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home
4.98 out of 5 average rating, 128 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home
4.98 out of 5 average rating, 146 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Top guest favourite
A scenic view captures a lush landscape with rolling hills, vineyards, and olive trees under a colorful sunset. The traditional Tuscan casolare is visible in the background, surrounded by greenery, while the horizon features soft hues of orange and pink.
Flat
4.99 out of 5 average rating, 315 reviews

Laura Chianti Holidays

Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility immersed in the Chianti countryside. The apartment, halfway between Florence and Siena, is conveniently located for quick access to Florence, Siena, San Gimignano , Volterra, as well as the beautiful Chianti hills. The apartment offers private parking, two bedrooms, a fully equipped kitchen, private bathroom, private garden, barbecue, and a wonderful view of the Chianti hills.

Top guest favourite
A well-equipped kitchen is presented, featuring wooden cabinets and a modern stove. A dining table with colorful floral patterns is set for two. Large windows allow natural light to fill the space, while a small plant adds a touch of greenery.
Apartment
4.97 out of 5 average rating, 272 reviews

Casa Amaryllis

Delightful two-room apartment located on the first floor in a central area. It consists of a living area with a sofa, kitchen, and laptop; a bedroom with a very comfortable double bed; a bathroom with a spacious and comfortable shower. Suitable for up to 2 people. Has a large terrace. It is a 10-minute walk to the station. Free parking in front of the house or at most within 200 m. Wi-Fi access available. You can walk to Siena Eye Laser in a few minutes.

Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa
4.96 out of 5 average rating, 190 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Popular amenities for Poggibonsi holiday rentals

When is the best time to visit Poggibonsi?

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Avg. price£58£57£63£67£68£69£71£70£71£69£66£69
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in Poggibonsi?

    Poggibonsi has accommodations in its historic center, near the main piazzas, and around the Tuscan countryside just outside town. Staying near the old town allows guests to explore winding streets, markets, and local cafes with ease.

  • What are the best things to do in Poggibonsi with kids?

    Families frequently visit the Parco Archeodromo, discover local playgrounds, or explore the medieval fortress together. Sampling gelato in town is often suggested for children, adding a sweet highlight to the day.

  • What are some of the best things to do in Poggibonsi?

    Explore the Fortezza di Poggio Imperiale, stroll through the historic center, or discover the Parco Archeodromo, which brings medieval life to the present. Local markets and seasonal food festivals help visitors experience Tuscan traditions firsthand.

  • How is the weather in Poggibonsi?

    Poggibonsi has mild winters, with temperatures near 37–55°F (3–13°C), and warm summers around 65–90°F (18–32°C). Spring and autumn feature comfortable conditions and moderate rainfall, making them pleasant times to explore outdoors.

  • When is the best time to visit Poggibonsi?

    Late spring and early autumn are often recommended for visits, as temperatures are comfortable and the landscape is especially vibrant. This period also sees several local festivals, blending cultural experiences with mild weather.

  • What are the best places to visit in Poggibonsi?

    Poggibonsi has the Fortezza di Poggio Imperiale, Parco Archeodromo, and the historic Basilica di San Lucchese, all frequently suggested for their cultural and architectural interest. The town's markets and artisan shops also offer a glimpse into local life.

  • What are some hiking trails in Poggibonsi?

    Poggibonsi has countryside paths winding between gentle hills and vineyards. Many visitors enjoy wandering along rural lanes, discovering views of local castles and olive groves scattered around the area.

  • What are some family activities we can do in Poggibonsi?

    Explore the interactive exhibits at the Parco Archeodromo, enjoy outdoor fun at local parks, or create lasting memories at the town’s frequent food and seasonal festivals. Gelato shops and small pizzerias give families welcoming spots to relax together.

  • What are some of the best day trip ideas from Poggibonsi?

    Visitors often head out to explore medieval towns like San Gimignano and Siena, or vineyards dotted across the Tuscan countryside. Art enthusiasts can discover historic abbeys and regional museums in towns around Poggibonsi.

  • Are there any pet friendly accommodations available in Poggibonsi?

    Many accommodations in Poggibonsi welcome pets, especially those in the countryside and residential zones around the town. Look for stays with access to nearby parks or outdoor spaces for extra convenience.

  • What are some local tips for visiting Poggibonsi?

    Mornings are a great time to explore local markets and bakeries before crowds arrive. Taking time to greet shopkeepers and trying regional specialties can enhance your experience of everyday Poggibonsi life.

  • What is Poggibonsi known for?

    Poggibonsi is recognized for its medieval heritage, with historic fortresses and archaeological parks reflecting its Tuscan past. The town is also noted for local food traditions and its role as a hub among classic wine regions.

  • What are the best hidden gems to explore in Poggibonsi?

    Explore the Fonte delle Fate, a medieval fountain tucked near town, and visit the Fortezza di Poggio Imperiale, which has broad ramparts with local history. Artisan workshops and smaller churches offer quieter perspectives on Poggibonsi’s community.

  • What are the best foods to try in Poggibonsi?

    Poggibonsi has robust Tuscan flavors—try pici pasta, locally made pecorino cheese, and dishes featuring wild boar. Bakeries are known for schiacciata, a type of savory focaccia, and food shops often sell fresh regional olive oil.

  • What should I bring for a trip to Poggibonsi?

    Comfortable walking shoes and layers are useful, as historic streets can be uneven and temperatures vary by season. Bringing a light rain jacket, especially in autumn and spring, and a sunhat for summer, helps you adapt to changing weather.

  • What is the nightlife in Poggibonsi like?

    Poggibonsi’s nightlife centers around local wine bars, relaxed cafes, and occasional live music in piazzas. The town has a laid-back atmosphere where evenings are often spent enjoying regional wines and conversation.

  • What are the most popular events or festivals in Poggibonsi?

    Poggibonsi hosts seasonal food fiestas and medieval-themed celebrations, often held in spring and early autumn. Local markets and music events in the historic center attract both residents and visitors throughout the year.

  • Are there family friendly vacation rentals in Poggibonsi?

    Many vacation rentals in Poggibonsi are welcoming for families, with options ranging from homes in quiet residential areas to cozy apartments near parks and main piazzas. Look for amenities such as kitchens and outdoor space for added comfort.

Quick stats about holiday rentals in Poggibonsi

  • Total holiday rentals

    Explore 100 holiday rentals in Poggibonsi

  • Nightly prices starting at

    Poggibonsi holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 6,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Poggibonsi holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Poggibonsi rentals

  • 4.8 Average rating

    Poggibonsi stays are highly rated by guests – averaging 4.8 out of 5!

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