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Holiday rentals in Poggibonsi

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Top-rated holiday rentals in Poggibonsi

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An aerial view captures a historic farmhouse surrounded by lush vineyards and olive groves in the Chianti region. A tranquil pool is positioned in a spacious courtyard, with sun loungers nearby, offering serene countryside vistas that extend into the horizon.
Apartment
5 out of 5 average rating, 201 reviews

Antico Podere del 1600 nel Chianti in Toscana

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana. L'appartamento è arredato in perfetto stile tradizionale dell'antica Toscana : travi in legno, pavimenti in cotto e arredamenti curati e prodotti da artigiani locali che vi faranno vivere un piacevole soggiorno . Nel grande cortile esterno troverete una piscina a sale su terrazza panoramica con stupenda vista su castello colline e vigneti con tramonti mozzafiato.

Guest favourite
Home
4.96 out of 5 average rating, 130 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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
4.95 out of 5 average rating, 134 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, 231 reviews

Tramonto sul Chianti Classico

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
4.94 out of 5 average rating, 193 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
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, 324 reviews

Laura Chianti Vacanze

Laura Chianti Vacanze è la soluzione ideale per chi cerca pace e tranquillità immerso nelle campagne del Chianti. L'appartamento, a metà strada tra Firenze e Siena, si trova in una posizione strategica per raggiungere velocemente Firenze, Siena, San Gimignano , Volterra, nonché le meravigliose colline del Chianti. L'appartamento dispone di ampio parcheggio privato, due camere, cucina attrezzata, bagno privato, giardino privato, barbecue, ed una stupenda vista sulle colline del Chianti.

Top guest favourite
A tranquil landscape is captured at sunrise, with the sun rising above a misty valley. Soft golden light filters through layered clouds, illuminating the distant hills. The scene conveys a sense of peace and natural beauty, set against a backdrop of serene fog.
Flat
4.93 out of 5 average rating, 126 reviews

Appartamento con giardino panoramico San Gimignano

Situato a ridosso delle mura di San Gimignano, l’ appartamento è immerso nella natura con ogni confort desiderabile ed una vista panoramica stupefacente. L’appartamento è composto da 1 cucina, 1 camera da letto matrimoniale, 1 stanza soggiorno-pranzo, giardino panoramico e posteggio auto riservato di fianco alla casa. -2 minutes walk from the city center, surrounded by nature -panoramic view -every desirable confort -private parking -1 kitchen, 1 bedroom, 1 bathroom, 2 living room

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, 216 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.

Guest favourite
A serene bedroom features a spacious bed with a checkered blanket and layered pillows. Natural light filters through sheer curtains, illuminating the warm tones of the room. An armchair is positioned beside the window, enhancing the cozy atmosphere.
Flat
4.92 out of 5 average rating, 111 reviews

Appartamento Lo Scrigno

L'appartamento è un open space di recente ristrutturazione da cui sono stati ricavati un accogliente soggiorno con cucina e una camera matrimoniale; dispone, inoltre, di lavatrice, lavastoviglie, WI-FI, aria condizionata, riscaldamento e smart TV. Si trova a 10 minuti a piedi dalla stazione e a 5 minuti a piedi dal centro oculistico ‘Siena Eye Laser’. Parcheggi gratuiti nelle immediate vicinanze dell'appartamento.

Guest favourite
The kitchen area features modern cabinetry and a compact dining table surrounded by four chairs. A vibrant centerpiece of flowers is placed on the table. Natural light enters through a window, illuminating the sleek floor design.
Flat
4.9 out of 5 average rating, 148 reviews

Appartamento accogliente in zona centrale

COMODISSIMO APPARTAMENTO composto da due camere, bagno e soggiorno-cucina con luminoso affaccio su ampia terrazza, situato vicino alla clinica Siena Eye Laser, al centro e ai principali servizi di trasporto, dista infatti circa 600 mt dalla stazione ferroviaria e circa 50 mt dalla fermata del bus. Possibilità di parcheggio gratuito per chi si sposta in auto. Non è consentito fumare all'interno dell'appartamento.

Top guest favourite
A cozy living room features two reclined leather chairs and a wooden table, complemented by a decorative rug. A rustic fireplace is positioned against a wall, and framed artworks adorn the space. Natural light streams through two wooden windows, enhancing the warm ambiance.
Flat
5 out of 5 average rating, 125 reviews

Villa Mocarello " IL LECCIO"

This romantic apartment is located on the second floor of a 19th century Leopoldinian Villa. The independent entrance can be reached walking through the lush garden surrounding the house. The Villa is located in a strategic position in the middle of Tuscany, close to Florence, Siena and San Gimignano. the bus station is about ten minutes on foot, the train station about fifteen minutes,

Top guest favourite
A charming garden area features a round table surrounded by four wrought iron chairs. Vibrant flowers bloom in planters, and lush greenery adds to the tranquil environment. A rustic stone wall and traditional rooftops provide a picturesque backdrop, enhancing the sense of privacy.
Home
4.99 out of 5 average rating, 209 reviews

Romantic Garden in Historic San Gimignano

Enjoy a romantic stay in the heart of San Gimignano, inside the medieval walls.The apt features a private garden, a rare and peaceful corner where you can have breakfast, relax after exploring the town or enjoy a glass of wine in the evening. Perfect for couples looking for charm, history and quiet retreat in one of Tuscany's most beautiful villages.

Popular amenities for Poggibonsi holiday rentals

When is the best time to visit Poggibonsi?

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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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