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

287 M² Villa ∙ 8 Bedrooms ∙ 16 Guests - Poggibonsi
No reviews

287 M² Villa ∙ 8 Bedrooms ∙ 16 Guests

house, San Gimignano
Villa Arnilù, in San Gimignano, offers a large, self-catering property within walking distance of the historic centre and its towers.
This 287 square metre villa sleeps 16 guests in 8 bedrooms and 8 bathrooms, boasting a private pool, garden, parking, and pet-friendly facilities.
250 M² House ∙ 6 Bedrooms ∙ 17 Guests - Poggibonsi
10 1 review

250 M² House ∙ 6 Bedrooms ∙ 17 Guests

house, Certaldo
Podere Galieni is an 8-room cottage situated a short distance from Certaldo, offering 250 m² of renovated living space with panoramic views of the Tuscan countryside and San Gimignano. This spacious country house provides accommodation for up to 16 guests, featuring air conditioning, WiFi, a private swimming pool, and convenient on-site parking.
Cosy Apartment In Villa For 3 People With A/c, Pool And Tv, Close To Siena - Poggibonsi
No reviews

Cosy Apartment In Villa For 3 People With A/c, Pool And Tv, Close To Siena

house, Poggibonsi
La Fiumara, near Castellina Scalo (2km from Poggibonsi), offers easy access to Siena (23km) and San Gimignano (26km), with nearby attractions including the Rock of Staggia and Monteriggioni Castle.
This one-bedroom property, boasting 62 square metres of floor space, sleeps three guests and includes a swimming pool (open June 1st to September 15th), a garden, parking, and air conditioning; nearby activities include hiking the Sentierelsa Trail and wine tasting at Casa Vinicola Luigi Cecchi.
Agriturismo Il Casolare Di Bucciano - Poggibonsi
9.0 1168 reviews

Agriturismo Il Casolare Di Bucciano

farm, San Gimignano
Il Casolare Di Bucciano is a historic farmhouse located 2 kilometres from the Towers of San Gimignano, offering stunning views of the iconic landmark.
This family-friendly accommodation provides 1 bedroom, 1 bathroom, air conditioning, a swimming pool, an on-site restaurant serving local cuisine, and opportunities to purchase farm produce such as Vernaccia and Chianti wines.

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

La Ripa - Appartamento Il Fienile - Poggibonsi
9.4 202 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.
Villa Torre With Pool And Ac - Poggibonsi
No reviews

Villa Torre With Pool And Ac

house, Poggibonsi
Casolare Torre offers a spacious 260 square metre Tuscan farmhouse in the Chianti region, 48 kilometres from Florence and 32 kilometres from Siena, with easy access to San Gimignano and Radda in Chianti. This pet-friendly property accommodates up to 15 guests across 8 bedrooms and 5 bathrooms, featuring an infinity swimming pool, air conditioning, Wi-Fi, and private parking.
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.
305 M² Farmhouse ∙ 10 Bedrooms ∙ 20 Guests - Poggibonsi
No reviews

305 M² Farmhouse ∙ 10 Bedrooms ∙ 20 Guests

farm, Barberino Tavarnelle
Podere San Bartolo, situated in Barberino Val d'Elsa, offers a large farmhouse rental near Barberino Tavarnelle, conveniently located for exploring the Chianti and Siena regions.
This 305 square metre property comprises three spacious apartments, sleeping up to 20 guests, and boasts a private pool, garden, barbecue, and high-speed Wi-Fi, plus the option of private Tuscan dinners.

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

Casa In Corso, Colle Val Delsa - Poggibonsi
10 11 reviews

Casa In Corso, Colle Val Delsa

house, Colle di Val d'Elsa
This two-bedroom flat is situated in Colle di Val d'Elsa Alta, directly opposite the Town Hall, offering immediate access to the historic centre and convenient proximity to San Gimignano (15 km), Monteriggioni (16 km), Siena (40 km), Volterra (30 km), and Florence (50 km).
This property accommodates up to four guests and features a fully equipped kitchen, free Wi-Fi, and private covered parking, providing essential comforts and conveniences for exploring Tuscany.
Rignana Estate, Pool & Tennis - Poggibonsi
No reviews

Rignana Estate, Pool & Tennis

farm, Greve in Chianti
Villa Rignana, a recently renovated farmhouse in Greve in Chianti, is conveniently located 8km from Piazza Matteotti and offers easy access to Florence (34km from Pitti Palace and 40km from Florence Airport).
This country estate boasts an infinity pool, tennis court, restaurant, and on-site yoga classes, alongside fully equipped kitchens, private bathrooms, and a terrace; bike rentals are available for exploring the Chianti countryside.
Stunning Private Villa With Wifi, Private Pool, A/c, Hot Tub, Tv, Patio, Close To San Gimignano - Poggibonsi
9.0 9 reviews

Stunning Private Villa With Wifi, Private Pool, A/c, Hot Tub, Tv, Patio, Close To San Gimignano

house, Poggibonsi
This detached villa in Poggibonsi is set amongst vineyards and olive groves, conveniently located between Florence and Siena, 18 kilometres from San Gimignano and 40 kilometres from Siena.
This property offers 360 square metres of living space for up to 12 guests across a main house and a separate guest house, featuring air-conditioned bedrooms, a large swimming pool with panoramic views, a garden, a barbecue, a gazebo, a wood-burning oven, and complimentary Wi-Fi.
Villa Vianci Rbo, Your Home Away In Tuscany - Poggibonsi
9.4 12 reviews

Villa Vianci Rbo, Your Home Away In Tuscany

house, Poggibonsi
Villa Vianci RBO is located in the Tuscan countryside, 19 kilometres from Siena's Piazza del Campo and 32 kilometres from Poggibonsi's Piazza Matteotti. This property has excellent user, location and cleanliness ratings.
The villa offers seven bedrooms, spread over 500 square metres, making it ideal for large groups or families. Guests can enjoy a private swimming pool, barbecue facilities, a picnic area, a tennis court, and a restaurant with room service, all set within a beautiful garden with mountain views.

Best Poggibonsi villas and holiday homes with a garden

La Ripa - Appartamento I Nidi - Poggibonsi
8.7 3 reviews

La Ripa - Appartamento I Nidi

house, San Gimignano
La Ripa - Appartamento I Nidi is a self-catering property in San Gimignano, approximately 34km from Piazza Matteotti and 37km from Piazza del Campo, offering easy access to Tuscany's major attractions.
This 70 square metre house sleeps up to 12 guests in two bedrooms and one bathroom, and boasts a private pool, free Wi-Fi, free parking, a fully equipped kitchen, barbecue, children's playground, and a garden.
Nice Apartment In Villa For 6 People With Pool, Tv And Patio - Poggibonsi
No reviews

Nice Apartment In Villa For 6 People With Pool, Tv And Patio

house, Poggibonsi
This rural estate is located in the Chianti region, 14 kilometres from Castellina in Chianti and 18 kilometres from San Gimignano, offering a convenient base for exploring the area.
This 'Tipologia Trilo' apartment offers rustic interiors, sleeping up to six guests with two bedrooms and one bathroom, and features access to a shared swimming pool, garden, and barbecue facilities.
I Melograni Del Chianti - Poggibonsi
9.5 103 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.
Villa Arnilù - Poggibonsi
No reviews

Villa Arnilù

house, San Gimignano
Villa Arnilù is a detached villa located in San Gimignano, offering a secluded escape within easy reach of the town's historic centre.
This pet-friendly property accommodates up to 16 guests across 8 bedrooms and 8 bathrooms, featuring a private garden with a fenced swimming pool, a fully equipped kitchen with a dishwasher, and Wi-Fi, with breakfast and homemade products available upon request.
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