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Holiday houses in Poggibonsi

Find and book unique accommodation on Airbnb

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 $28 AUD 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.

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Guest favourite
Apartment in Poggibonsi
4.82 out of 5 average rating, 119 reviews

Da "Jack e Adriana".

Rilassati con tutta la famiglia in questo alloggio tranquillo. Spazioso appartamento a Poggibonsi, mobili in stile fiorentino e curato nei minimi particolari. Corredato di due posti auto riservati, di cui uno coperto. 18 minuti dalla Clinica Siena Eye Laser. In 15 minuti a piedi si raggiungono la Stazione Ferroviaria ed il Centro Commerciale. A 5 minuti a piedi dal tabacchi, bar, panificio, piscina pubblica e pista ciclopedonale. Perfetto per le città Siena, Firenze, San Gimignano e Volterra.

Top Guest favourite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5.0 out of 5 average rating, 218 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 con la possibilità di organizzare servizi ed esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con stupenda vista su castello colline e vigneti con tramonti mozzafiato.

Top Guest favourite
A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.
Villa in Poggibonsi
4.99 out of 5 average rating, 97 reviews

Villa L'Olivo w/Private pool (Close San Gimignano)

Villa L’Olivo si trova nella campagna Toscana, a circa 10 chilometri da San Gimignano e a pochi minuti dai supermercati ed i vari servizi presenti a Poggibonsi. La nostra Villa è un ottimo punto di partenza per scoprire tutte le bellezze della Toscana, ma è anche un luogo ideale per chi ama concedersi una pausa dalla vita frenetica della città. A Villa L’Olivo, puoi prenotare una cena con chef privato, direttamente in villa, per goderti una cena toscana in tutta tranquillità. Scrivici per info!

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.
Condo in Poggibonsi
4.95 out of 5 average rating, 151 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.

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 in Poggibonsi
4.94 out of 5 average rating, 204 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 serene outdoor pool is situated in front of a rustic stone building, featuring multiple windows and a terracotta roof. Lush greenery and olive trees are visible, while lounge chairs line the pool area, all set against a clear blue sky.
Farm stay in Poggibonsi
4.98 out of 5 average rating, 49 reviews

I Melograni del Chianti - Apt. Focolare

Il Focolare è situato al 1° piano dei Melograni del Chianti: sono 75mq. suddivisi fra un ingresso, soggiorno con cucina, una camera matrim., una camera con letto matrim. + un letto singolo e 2 bagni. Nel giardino ci sono tante aree comuni dove potete gustare le Vs. colazioni, pranzi e cene all'aperto: il patio, la terrazza belvedere, la zona BBQ etc. Oltre alla piscina e al solarium, i ns. clienti possono usufruire della lavanderia e della cantinetta per le degustazioni di prodotti aziendali.

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.
Apartment in Poggibonsi
4.98 out of 5 average rating, 337 reviews

Laura Chianti Vacanze

Laura Chianti Vacanze è la soluzione ideale per chi cerca pace e tranquillità immerso nelle campagne del Chianti. L'appartamento è 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.

Superhost
A cozy seating area is presented with a blue sofa and an armchair, complemented by a light wood coffee table. Wall sconces provide soft lighting, while framed botanical art adds a touch of nature. Flowing curtains grace the window, allowing natural light to filter in.
Condo in Poggibonsi
4.88 out of 5 average rating, 59 reviews

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.

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.
Condo in Poggibonsi
4.98 out of 5 average rating, 288 reviews

Casa Amaryllis

Delizioso bilocale posto al primo piano in zona centrale. E' formato da zona giorno con cucina divano e lap top; camera da letto con comodissimo letto matrimoniale; bagno con doccia spaziosa e confortevole. Adatto ad ospitare al massimo 2 persone. Dotato di ampia terrazza. Si trova a 10 minuti a piedi dalla stazione. Parcheggio libero gratuito antistante l'abitazione o al massimo entro 200 m. Accesso Wi-Fi disponibile. Siena Eye Laser raggiungibile a piedi in pochi minuti.

Guest favourite
An open living area is showcased, featuring wooden beams on the ceiling. A spacious sofa sits adjacent to a coffee table, with a guitar resting nearby. Various art pieces decorate the walls, while plants and decorative items enhance the inviting ambiance.
Condo in Poggibonsi
4.93 out of 5 average rating, 83 reviews

Casa Yuri a Poggibonsi

Ampio e luminoso appartamento nel centro storico di Poggibonsi. Il soggiorno ha tre grandi finestre ad arco con vista sulle colline del Chianti. Dotato di aria condizionata, due camere da letto e due bagni, è adatto anche per soggiorni prolungati. La posizione è strategica: a duecento metri dalla stazione ferroviaria e dalla fermata degli autobus per raggiungere facilmente le principali città d'arte della Toscana. L'appartamento è situato al terzo piano, senza ascensore.

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

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.

Top Guest favourite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano
4.92 out of 5 average rating, 385 reviews

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti.

Popular amenities for Poggibonsi holiday rentals

When is the best time to visit Poggibonsi?

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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.