
Holiday rentals 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 £15 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 & 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!
Top-rated holiday rentals in Poggibonsi
Guests agree: these stays are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to your needs. The apartment is available for 2 adults with the possibility 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 overlooking the castle, hills and vineyards with unique sunsets.

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.

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.

Tuscan House with Private Jacuzzi in Chianti
An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

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.

Private Courtyard | 3BR/3BA | Garage
Welcome to Casa Costarella.<br><br>Wake up in San Gimignano’s historic center and step into your own private courtyard — a rare feature within the city walls.<br><br>This 120 m² / 1,290 sqft residence spans two levels and blends preserved historic character with modern comfort.<br><br>☞ Enclosed private courtyard<br>☞ 3 bedrooms / 3 full bathrooms<br>☞ Free covered garage for 1 car (5-minute walk)<br>☞ Underfloor heating & cooling<br>☞ High-speed Wi-Fi<br>☞ Self check-in<br><br>

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.

AnticaVista, Luxury Apartment with Tower Views
A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Luxury Medieval Tower • Exclusive Chianti Stay
Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

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.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Herons Superior Apartment - Splendid view!
Goditi una vacanza all'insegna dello stile in questo spazio nel centro di San Gimignano. Finemente arredato e con una vista spettacolare sulle colline toscane, Herons Superior Apartment è pronto a ospitarti insieme alle persone che ami. ___________________________________________________ Tassa di soggiorno da pagare sul posto secondo il seguente calcolo: 2,5€ X numero di ospiti sopra gli 11 anni X numero di notti (si pagano al massimo 5 notti).
Popular amenities for Poggibonsi holiday rentals
Other great holiday rentals in Poggibonsi

Charming apartment in the historic center

Penthouse in small medieval castle near Florence

Casa Yuri in Poggibonsi

Cozy Tuscany base - 10 min San Gimignano

Happy Stay in a Tuscany Home with Stunning Views

Poggiolo

Cipressini 2 - pool and amazing views

Palazzina Maresa - Loft 4
When is the best time to visit Poggibonsi?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £69 | £69 | £68 | £67 | £68 | £69 | £71 | £70 | £71 | £69 | £66 | £69 |
| 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
- Pet-friendly rentals Poggibonsi
- Rentals with a washing machine and dryer Poggibonsi
- Rentals with outdoor seating Poggibonsi
- Apartment rentals Poggibonsi
- Rentals with pools Poggibonsi
- Rentals with a patio Poggibonsi
- Family-friendly rentals Poggibonsi
- Villa rentals Poggibonsi
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- 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
- Mercato Centrale
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Spiagge Bianche
- Piazza della Repubblica
- Parco delle Cascine
- Gulf of Baratti
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria





