
Holiday houses in Poggibonsi
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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 $34 NZD per night before taxes and fees

Verified guest reviews
Over 6,630 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
90 of Poggibonsi holiday rentals include Wi-Fi 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!
Top-rated holiday rentals in Poggibonsi
Guests agree: these stays are highly rated for location, cleanliness and more.

Historic 17th-century farmhouse in Chianti, Tuscany
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing exclusive services and experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace with a wonderful view of the castle, hills, and vineyards with breathtaking sunsets.

Gallery Apartment near Chianti
Comfortable and bright apartment in the center of Poggibonsi, 150 meters from the Siena Eye Laser Clinic and all the necessary amenities. Ample public parking adjacent to the building. Conveniently located for reaching the cities of art, such as Florence, Siena, San Gimignano, Volterra, Pisa and the beautiful villages of Chianti. Gallery Apartment is equipped with all amenities and will welcome you as if you were at home. You can sit at the tables on the 2 terraces and drink a good Chianti or coffee in the morning.

From "Jack and Adriana."
Relax with the whole family in this quiet accommodation. Spacious apartment in Poggibonsi, furnished in Florentine style and with attention to the smallest details. Equipped with two reserved parking spaces, one of which is covered. 18 minutes from the Siena Eye Laser Clinic. In 15 minutes on foot you can reach the train station and the shopping mall. A 5-minute walk to the tobacco shop, bar, bakery, public pool and bike/pedestrian path. Perfect for the cities of Siena, Florence, San Gimignano and Volterra.

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.

I Melograni del Chianti - Focolare Apartment
Il Focolare is located on the 1st floor of Melograni del Chianti: 75 sqm divided between an entrance, living room with kitchen, a double bedroom, a bedroom with a double bed + a single bed and 2 bathrooms. In the garden, there are many common areas where you can enjoy your breakfasts, lunches and dinners outdoors: the patio, the panoramic terrace, the BBQ area, etc. In addition to the pool and solarium, our customers can take advantage of the laundry and cellar for tastings of farm products.

Maestra Exclusive Chianti House, Tuscany
Spacius and elegant apartment just renovated . Furnished in full Tuscan taste and located in the historic center of Poggibonsi, a medieval town strategically connected to the most famous tourist destinations in Tuscany such as San Gimignano, Certaldo, Volterra, Monteriggioni, Castellina, Radda Gaiole and Greve in Chianti, Siena and Florence. Wide spaces, frescoes, wooden beams, fireplace, handcrafted furnishings combined with modern services such as the Jacuzzi, will brighten your stay.

Villa L'Olivo w/Private pool (Close San Gimignano)
Villa L'Olivo is located in the Tuscan countryside, about 10 kilometers from San Gimignano and a few minutes from the supermarkets and various services in Poggibonsi. Our Villa is a great starting point to discover all the beauty of Tuscany, but it is also an ideal place for those who love to take a break from the hectic life of the city. At Villa L'Olivo, you can book a dinner with a private chef, directly in the villa, to enjoy a Tuscan dinner in peace. Write to us for info!

Laura Chianti Holidays
Laura Chianti Vacanze is the ideal solution for those seeking peace and tranquility in the heart of the Chianti countryside. The apartment is halfway between Florence and Siena, and is in a strategic position for quickly reaching Florence, Siena, San Gimignano, Volterra, as well as the wonderful Chianti hills. The apartment has ample private parking, two bedrooms, an equipped kitchen, a private bathroom, a private garden, a barbecue, and a wonderful view of the Chianti hills.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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.

Casa Yuri in Poggibonsi
Large and bright apartment in the historic center of Poggibonsi. The living room has three large arched windows overlooking the Chianti hills. Equipped with air conditioning, two bedrooms and two bathrooms, it is also suitable for extended stays. The location is strategic: two hundred meters from the train station and the bus stop to easily reach the main cities of art in Tuscany. The apartment is located on the third floor, without an elevator.

Poggio Massiccioli
Cozy apartment for 4 people furnished in Tuscan style and with exposed beams nestled among the rolling hills of the Tuscan countryside. Available to guests is an equipped garden, free Wi-Fi, a shared equipped swimming pool, a wood-burning oven and barbecue, and a washing machine. The apartment was converted from a charming 19th-century stone farmhouse recently renovated according to Tuscan tradition and divided into three comfortable apartments.
Popular amenities for Poggibonsi holiday rentals
Stay near Poggibonsi's top sights
Other great holiday rentals in Poggibonsi

Luxury Medieval Tower • Exclusive Chianti Stay

2nd House in the Historic Village

Herons Superior Apartment - Splendid view!

AnticaVista, Luxury Apartment with Tower Views

Exclusive Villa with Pool in the Chianti Classico Area

Il Castro Luxury San Gimignano. Michelangelo Suite

Relax in Chianti countryside

Casa Palme
When is the best time to visit Poggibonsi?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 NZD | $156 NZD | $155 NZD | $156 NZD | $156 NZD | $155 NZD | $161 NZD | $160 NZD | $161 NZD | $156 NZD | $151 NZD | $158 NZD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°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.
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Spiagge Bianche
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





