Villas and Holiday homes in Poggibonsi

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Poggibonsi holiday homes
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41 Villa rentals in Poggibonsi

Best Poggibonsi villas and holiday homes with a pool

Among the 41 accommodations in Poggibonsi, here are the 4 best villas and holiday homes with a pool

La Ripa - Appartamento Il Fienile - Poggibonsi
9.4 203 reviews

La Ripa - Appartamento Il Fienile

house, San Gimignano
La Ripa - Appartamento Padronale is a short distance from San Gimignano's historic centre, making it easy to explore the town's charming streets and iconic towers. The property has received excellent ratings for its location, cleanliness and overall experience.
This two-bedroom house offers comfortable accommodation for families or groups of friends. It has a private patio with garden views, a shared swimming pool, a fully equipped kitchen and free Wi-Fi.
Holiday Home Bardeggiano - Caterina 7 By Interhome - Poggibonsi
8.8 23 reviews

Holiday Home Bardeggiano - Caterina 7 By Interhome

house, Colle di Val d'Elsa
Apartment Bardeggiano - Caterina 2 is located in Belvedere, a peaceful district of Colle di Val d'Elsa, just a short drive from the historic cities of Siena and San Gimignano. The property has received very good ratings for cleanliness, location and user experience.
This two-bedroom dwelling comes fully equipped with a kitchen, fridge, freezer, microwave, dishwasher and a private garden for relaxing. Guests can enjoy a terrace with views of the surrounding countryside, a swimming pool, and a bar and restaurant on-site.
Le Buche - Poggibonsi
8.6 4 reviews

Le Buche

farm, Poggibonsi
This charming farmhouse is situated in the heart of the Chianti Classico region, just 14km from Castellina in Chianti and within easy reach of Siena and Florence. It has received excellent reviews from previous guests, who have praised its peaceful location and the warm hospitality of the owners.
The property comprises three independent apartments, totalling 150 square metres and accommodating up to eight guests. Guests can enjoy a shared swimming pool, table tennis, and a barbecue, as well as the opportunity to purchase fresh, locally sourced farm products.
Podere Il Pino - Poggibonsi
8.7 591 reviews

Podere Il Pino

house, Poggibonsi
Podere Il Pino is a holiday home located in the Chianti Hills, just 10km from San Gimignano and a short drive from Colle di Val d'Elsa and Poggibonsi, offering a peaceful retreat in the heart of Tuscany. It has received very good ratings for location, cleanliness and user experience.
Each apartment comes with a private patio overlooking the large garden, providing a relaxing space to enjoy meals and the Tuscan sunshine. Guests can also enjoy the 18-metre pool with hydromassage jets, the small spa, the shared laundry room, and the tennis court.

Best family friendly Poggibonsi villas and holiday home

Among the 41 accommodations in Poggibonsi, here are the 4 best family friendly villas and holiday homes

Casa Vacanze Nel Chianti Il Granaio - Poggibonsi
9.0 51 reviews

Casa Vacanze Nel Chianti Il Granaio

house, Castellina in Chianti
Casa vacanze nel Chianti il Granaio is situated in Castellina in Chianti, Tuscany, approximately 34-52km from Florence's landmarks such as the Pitti Palace and Piazza del Campo in Siena.
This two-bedroom, two-bathroom villa offers a private tennis court, seasonal swimming pool with stunning pool views, and a well-equipped kitchen; free Wi-Fi and parking are also provided for guests.
Appartamento Il Poggino - Poggibonsi
9.8 17 reviews

Appartamento Il Poggino

house, Colle di Val d'Elsa
Appartamento il Poggino is located in Colle di Val d'Elsa, just 26 kilometres from the historic Piazza del Campo in Siena, offering views of the surrounding gardens and cityscape. This property has received excellent ratings for cleanliness and location, with a very good overall user rating.
The apartment provides 70 square metres of space, comfortably accommodating up to 5 guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, free Wi-Fi, a private patio, and free parking.
Agriturismo Capanna Delle Cozzole - Poggibonsi
9.6 29 reviews

Agriturismo Capanna Delle Cozzole

house, Castellina in Chianti
Agriturismo Capanna delle Cozzole is a family-friendly house in Castellina in Chianti, Tuscany, conveniently located 26km from Piazza Matteotti and 27km from Siena's Piazza del Campo.
This two-bedroom, two-bathroom property offers free Wi-Fi, air conditioning, a fully equipped kitchen with dishwasher, private parking, a terrace, garden, and barbecue facilities; ideal for exploring the Chianti region's hiking trails.
Torre Apt. Ground And First Floor - Poggibonsi
No reviews

Torre Apt. Ground And First Floor

farm, Poggibonsi
This farmhouse, Casolare Torre, offers a commanding position in the Chianti region, 48 kilometres from Florence and 32 kilometres from Siena, with convenient access to towns such as San Gimignano and Radda in Chianti.
The 60 square metre property sleeps up to four guests in two bedrooms and features air conditioning, complimentary WiFi, a kitchen with a fridge, microwave, and dishwasher, and access to a shared infinity pool set in a garden.

Frequently asked questions about villa rentals in Poggibonsi

  • What are the must-see attractions in and around Poggibonsi?

    Poggibonsi itself is a charming town with a historic centre and the impressive Fortezza di Poggibonsi, a 14th-century fortress. But you're also close to Siena, San Gimignano, and the Chianti region, all with their own unique attractions.
  • What are the best villa rentals in Poggibonsi?

    Among the villa rentals in Poggibonsi, Podere Il Pino, Antico Podere Il Bugnolo and Casajona Holiday are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Poggibonsi?

    You'll see plenty of birds, especially in the countryside, like swallows, robins, and owls. You might also spot wild boar, deer, and foxes, particularly in the hills around Poggibonsi.
  • What are the best villa rentals with a pool in Poggibonsi?

    Podere Il Pino, Antico Podere Il Bugnolo and Agriturismo La Moraia are the best villa rentals with a pool in Poggibonsi.

  • What is the best time to visit Poggibonsi?

    Spring and autumn are ideal, with mild temperatures and less crowds. Summer can be hot, but it's a great time for outdoor activities and festivals. Winter is quieter, but you might experience some rain.
  • What are the best villa rentals with a jacuzzi in Poggibonsi?

    The best villa rentals with a jacuzzi in Poggibonsi are Podere Il Pino, Casajona Holiday and Podere Oliveta.

  • When is it easiest to book a villa rental in Poggibonsi?

    Booking in advance is always recommended, especially for peak season. You'll find the best deals and availability outside of July and August, but it's still possible to find good options even in the summer.
  • What are the best villa rentals for families and kids in Poggibonsi?

    The best villa rentals for families and kids in Poggibonsi are Podere Il Pino, Antico Podere Il Bugnolo and Casajona Holiday.

  • What are the top hiking trails near Poggibonsi?

    The Sentiero del Chianti is a popular choice, offering stunning views of the vineyards and rolling hills. There's also the Via Francigena, an ancient pilgrim route that passes through the area.
  • What are the best pet friendly villa rentals in Poggibonsi?

    The best pet friendly villa rentals in Poggibonsi are Podere Il Pino, Antico Podere Il Bugnolo and Casajona Holiday.

  • What are the advantages of renting a house or a villa in Poggibonsi

    It offers more space and privacy compared to a hotel, allowing you to relax and enjoy the Tuscan lifestyle at your own pace. You'll often have access to a kitchen, so you can prepare your own meals and enjoy local produce.
  • What are the best villa rentals with parking in Poggibonsi?

    Podere Il Pino, Antico Podere Il Bugnolo and Casajona Holiday are the best villa rentals with parking in Poggibonsi.

  • Are there popular destinations near Poggibonsi?

    Absolutely! Siena, with its iconic Piazza del Campo, is just a short drive away. San Gimignano, known for its medieval towers, is also easily accessible. And of course, you're in the heart of the Chianti region, with its famous vineyards and wineries.

Popular destinations

Best Poggibonsi villas and holiday homes with parking

I Melograni Del Chianti - Poggibonsi
9.6 101 reviews

I Melograni Del Chianti

farm, Poggibonsi
I Melograni del Chianti farmhouse is conveniently located in Poggibonsi, approximately 32km from Siena's Piazza del Campo and the same distance from Piazza Matteotti in Poggibonsi itself, offering easy access to Tuscany's major landmarks.
This property boasts a seasonal outdoor pool, free Wi-Fi, private parking including an EV charging point (surcharge applies), and features spacious accommodation with private terraces, garden views, fully equipped kitchens, and amenities including yoga classes and barbecue facilities.
90 M² House ∙ 2 Bedrooms ∙ 4 Guests - Poggibonsi
No reviews

90 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Poggibonsi
This Poggibonsi terraced house, conveniently located within walking distance of the town's shops and restaurants, offers easy access to Poggibonsi's historical sites.
The 90 square metre, two-storey property sleeps four guests, boasting two bedrooms, two bathrooms, a fully equipped kitchen with modern appliances, a private courtyard, and amenities for families including a cot and high chair.
Nice Apartment In Villa For 4 People With Pool, Tv And Patio - Poggibonsi
No reviews

Nice Apartment In Villa For 4 People With Pool, Tv And Patio

house, Poggibonsi
This rural estate is situated amidst the vineyards and olive groves of Chianti, 14 kilometres from Castellina in Chianti and 18 kilometres from San Gimignano.
This 50 square metre apartment, suitable for up to four guests, features a living/dining area, a double bedroom, a kitchenette equipped with a microwave and dishwasher, and offers access to a shared garden and swimming pool, with Poggibonsi train station 5 kilometres away.
House Tuscany - Poggibonsi
10 1 review

House Tuscany

house, Poggibonsi
This Poggibonsi flat offers a prime base for exploring Tuscany, with the Chianti hills and towns such as San Gimignano, Monteriggioni, and Siena a short drive away, and Florence and Pisa reachable within an hour.
This one-bedroom apartment accommodates up to three guests and features air conditioning, a kitchen, and internet, providing an authentic Tuscan living experience ideal for cultural, gastronomic, and nature-focused itineraries.

Best Poggibonsi villas and holiday homes with a garden

Villa Del Biondo - Poggibonsi
9.5 32 reviews

Villa Del Biondo

house, Certaldo
Villa del Biondo is located in Certaldo, just 27 kilometres from Piazza Matteotti, offering scenic garden views and a peaceful setting. Guests consistently rate the accommodation excellent for its cleanliness, location, and overall experience.
The villa features spacious and comfortable units with seating and dining areas, perfect for relaxing after a day of exploring. Guests can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a terrace or balcony, a garden, and free Wi-Fi and private parking.
Villa Torre With Pool And Ac - Poggibonsi
No reviews

Villa Torre With Pool And Ac

house, Poggibonsi
Villa Torre With Pool And Ac in Piecorto offers proximity to Piazza Matteotti, 29 kilometres away, and Piazza del Campo, 32 kilometres away.
This spacious 8-bedroom villa, covering 260 square metres, accommodates up to 29 guests and features a private swimming pool, barbecue facilities, free on-site parking, complimentary WiFi, and a balcony with garden views.
Villetta Indipendente 100mq, Parco, Terrazzo, 2 Bagni E Ac - Poggibonsi
9.4 54 reviews

Villetta Indipendente 100mq, Parco, Terrazzo, 2 Bagni E Ac

house, Colle di Val d'Elsa
This two-bedroom house is located in Le Grazie, a short distance from the medieval town of San Gimignano, with Siena's Piazza del Campo being 29 km away.
The property features a private garden, a terrace, a sauna and parking, comfortably accommodating up to 10 guests in its 100 square metre space.
Cosy Apartment In Villa For 4 Guests With A/c, Pool And Tv, Close To Siena - Poggibonsi
8.0 1 review

Cosy Apartment In Villa For 4 Guests With A/c, Pool And Tv, Close To Siena

house, Poggibonsi
La Fiumara, near Castellina Scalo (2km) and a short drive from Siena (23km), offers three self-catering apartments ideal for exploring Tuscany's San Gimignano area.
This Poggibonsi property boasts 82 square metres of accommodation, sleeping four guests across two bedrooms and one bathroom, with a swimming pool, garden, parking, and air conditioning.
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