Holiday Rentals in Poggibonsi

132 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Poggibonsi holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

132 Holiday rentals and Airbnb in Poggibonsi

Best family friendly Poggibonsi holiday rentals

Among the 132 accommodations in Poggibonsi, here are the 4 best family friendly rentals

La Stalla - Poggibonsi
9.6 46 reviews
Poggibonsi
20/09 – 20/11
181 €/nighttotal: 11041 € (61 )

La Stalla

2 2
house , Monteriggioni
La Casa Del Fattore is a peaceful countryside retreat located 7 kilometres outside of Monteriggioni, a short drive from the historic city of Siena (16 kilometres) and the city of Florence (42 kilometres). The property has received excellent ratings for its location, cleanliness, and overall experience.
This self-catering accommodation offers a fully equipped kitchen, a private garden with a gazebo and barbecue, and a seasonal outdoor pool. Guests can enjoy a game of tennis or table tennis on-site, or explore the surrounding countryside on a bike, which can be rented from the property.
Agriturismo Bardeggiano-colle Val D'elsa - Poggibonsi
8.5 61 reviews
Poggibonsi
08/08 – 15/08
172 €/nighttotal: 1204 € (7 )

Agriturismo Bardeggiano-colle Val D'elsa

1 2
apartment , Colle di Val d'Elsa
Agriturismo Bardeggiano, in Colle di Val d'Elsa, offers a self-catering apartment 22.5km from Piazza del Campo in Siena and 37km from Piazza Matteotti.
This family-friendly property features a seasonal outdoor pool, garden, free Wi-Fi, private parking, and well-equipped kitchens in some units; enjoy the terrace, and explore the local crystal production.
Villa Dei 2 Ulivi (Abbadia Isola) - Poggibonsi
9.9 172 reviews
Poggibonsi
23/06 – 24/06
656 €/nightfor 1 night

Villa Dei 2 Ulivi (Abbadia Isola)

1 7
house , Monteriggioni
This family-friendly villa is located just 3.2 kilometres outside Monteriggioni, a short drive from the historic Monteriggioni Castle and set in the peaceful Tuscan countryside. It has received excellent ratings for user experience, location, and cleanliness.
The 250 square metre property offers 5 bedrooms with a sofa bed and 4 bathrooms. It also features a swimming pool, a jacuzzi, a tennis court, and a terrace with a garden, making it perfect for families and groups seeking a relaxing escape.
Casale Di Villore - Poggibonsi
9.8 416 reviews
Poggibonsi
08/10 – 14/10
173 €/nighttotal: 1038 € (6 )

Casale Di Villore

1 2
house , Poggibonsi
Casale di Villore is a charming country house located in Poggibonsi, just 48 kilometres from Florence, 30 kilometres from Siena and 18 kilometres from San Gimignano. The property boasts excellent user, location and cleanliness ratings.
The house offers spacious and comfortable accommodation with dining and seating areas. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, spa, tennis court, garden and a fully-equipped kitchen. There are also opportunities for horse riding and bike hire, allowing guests to explore the picturesque Tuscan countryside.

Best Poggibonsi holiday rentals with parking

Casa Anna "A Lovely Home In Tuscany" - Poggibonsi
9.9 107 reviews
Poggibonsi
05/08 – 12/08
268 €/nighttotal: 1876 € (7 )

Casa Anna "A Lovely Home In Tuscany"

3 5
house , Colle di Val d'Elsa
Casa Anna is located in the historic district of Colle di Val d'Elsa, a short walk from the charming Piazza Arnolfo and the Duomo, offering a peaceful retreat in the heart of this Tuscan town. The house has consistently received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
This three-bedroom, two-bathroom property features a spacious terrace with stunning views of the Tuscan countryside. Casa Anna offers a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, making it ideal for families and groups looking for a relaxing and active holiday.
Villetta - Poggibonsi
8.6 4 reviews
Poggibonsi
05/08 – 12/08
369 €/nighttotal: 2583 € (7 )

Villetta

3 5
farm , Poggibonsi
This 11th-century farmhouse, renovated in 1998, offers a secluded hilltop location near Colle di Val d'Elsa (4km), San Gimignano (14km), and Siena (24km), providing stunning countryside views and easy access to major Tuscan towns.
The 90 square metre property boasts three bedrooms, two bathrooms, sleeping up to six guests, and includes a swimming pool, terrace, and access to shared amenities such as a barbecue and table tennis.
350 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - Poggibonsi
Poggibonsi
05/08 – 12/08
1331 €/nighttotal: 9317 € (7 )

350 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

5 5
house , Barberino Tavarnelle
Villa Fiorentini, in San Filippo a Ponzano near Barberino Val d'Elsa in the Chianti region, offers a secluded escape in the Tuscan countryside, a short distance (a few kilometres) from both Florence and Siena.
This 350 square metre property boasts five bedrooms, five bathrooms, and sleeps up to ten guests, featuring a private swimming pool (10m x 5m), a large kitchen, and outdoor dining with a wood-fired oven; weekly linen and cleaning are included.
Casa Michelangelo - Poggibonsi
9.4 262 reviews
Poggibonsi
08/10 – 14/10
81 €/nighttotal: 486 € (6 )

Casa Michelangelo

1 2
apartment , Poggibonsi
Casa Michelangelo is a peaceful apartment situated in Megognano, a quiet village just 22 kilometres from the historic centre of Poggibonsi and 48 kilometres from Florence's Pitti Palace. This apartment has received excellent ratings for its location, cleanliness and overall experience.
This one-bedroom apartment offers 60 square metres of space, comfortably accommodating up to four guests. The property features a fully equipped kitchen, a private balcony, a garden, a tennis court, free parking and Wi-Fi, as well as the option to enjoy activities like fishing and hiking in the surrounding area.

Frequently asked questions about holiday rentals in Poggibonsi

  • What are some interesting places to visit in or near Poggibonsi?

    Poggibonsi is a great base for exploring Tuscany. You can visit the historic centre with its medieval walls and the Palazzo Pretorio. You can also visit the nearby town of Siena, famous for its Piazza del Campo, or the charming village of San Gimignano, known for its towers. For wine lovers, a trip to the Chianti Classico region is a must.
  • What are the best Airbnb and holiday rentals in Poggibonsi?

    Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine are among the best Airbnb and holiday rentals in Poggibonsi.

  • Which walking or cycling routes are the best in Poggibonsi?

    For a scenic walk, try the Sentiero degli Etruschi, which follows an ancient Etruscan route. For a longer cycle, the Via Francigena is a popular choice, passing through vineyards and olive groves. There are also plenty of shorter routes around the town, perfect for a casual ride.
  • What are the most popular Airbnbs in Poggibonsi?

  • What sports or outdoor activites can visitors enjoy in and around Poggibonsi?

    Poggibonsi is a great place for outdoor activities. You can go hiking in the surrounding hills, play tennis at the local courts, or go horseback riding in the countryside. There are also several golf courses in the area.
  • What are the best holiday rentals with a pool in Poggibonsi?

    Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine are the best holiday rentals with a pool in Poggibonsi.

  • What other towns or cities can be easily accessed from Poggibonsi?

    Poggibonsi is well-connected to other Tuscan towns and cities. You can easily take a train to Florence, Siena, or Pisa. You can also drive to other charming towns like San Gimignano, Volterra, and Monteriggioni.
  • What are the best rentals for families and kids in Poggibonsi?

    The best rentals for families and kids in Poggibonsi are Vacanze In Toscana Con Piscina, Podere Il Pino and Antica Casa Del Glicine.

  • What amenities are commonly available in vacation rentals in Poggibonsi?

    Vacation rentals in Poggibonsi typically offer a range of amenities, including a kitchen, bathroom, and laundry facilities. Some rentals may also have a private garden, swimming pool, or parking. You can find rentals ranging from cosy apartments to spacious villas.
  • What are the best rentals or Airbnbs with a jacuzzi in Poggibonsi?

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

  • What time of year is best to rent a vacation rental Poggibonsi?

    The best time to visit Poggibonsi depends on your preferences. Spring and autumn offer pleasant weather and fewer crowds. Summer is the peak season, with warm weather and plenty of events, but it can be busy. Winter is quieter and offers a different charm, with Christmas markets and festive decorations.

Destinations nearby

Best Poggibonsi holiday rentals with a balcony

Casa Di Piera - Poggibonsi
Poggibonsi
08/08 – 15/08
85 €/nighttotal: 595 € (7 )

Casa Di Piera

1 2
apartment , Poggibonsi
This spacious one-bedroom flat, Casa di Piera, is located in Poggibonsi, offering convenient access to Tuscan landmarks with Piazza Matteotti 27 kilometres and Piazza del Campo 29 kilometres away.
This air-conditioned residence spans 70 square metres, accommodating up to nine guests with a fully equipped kitchen, complimentary WiFi, private parking, and garden views from its terrace, perfect for exploring the region.
Villa Lionella Grande: A Splendid Three-story Villa Surrounded By Meadows And By Green Hills, With Free Wi-fi. - Poggibonsi
10 2 reviews
Poggibonsi
30/06 – 03/07
3392 €/nighttotal: 10176 € (3 )

Villa Lionella Grande: A Splendid Three-story Villa Surrounded By Meadows And By Green Hills, With Free Wi-fi.

8 5
house , Poggibonsi
Villa Lionella Grande is situated in the countryside near Poggibonsi, just 3.5 km from the town centre and 1.5 km from the nearest restaurant, offering a peaceful retreat with easy access to local amenities. This property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
This spacious villa accommodates up to 24 guests with 12 bedrooms, each featuring an en-suite bathroom, providing privacy and comfort for all. Guests can enjoy a private swimming pool, a large garden with a barbecue and wood-fired pizza oven, a gazebo for relaxing, and a choice of two fully equipped kitchens.
One Belvedere Tuscany - Poggibonsi
9.4 11 reviews
Poggibonsi
07/08 – 09/08
529 €/nighttotal: 1058 € (2 )

One Belvedere Tuscany

1 1
farm , Poggibonsi
One Belvedere Tuscany, a farmhouse in Poggibonsi, is situated 27km from both Piazza del Campo in Siena and Piazza Matteotti.
This property boasts an infinity pool, on-site spa with sauna and hot tub, fitness centre, restaurant serving local specialities, and free private parking; bike and car rentals are available for exploring the Tuscan countryside.
Podere Val Di Gallo - Poggibonsi
9.4 338 reviews
Poggibonsi
08/10 – 14/10
116 €/nighttotal: 696 € (6 )

Podere Val Di Gallo

2 2
apartment , Poggibonsi
Podere Val di Gallo is a peaceful apartment located in the Tuscan countryside, 32km from the historic Piazza del Campo in Siena and 35km from Piazza Matteotti in Poggibonsi. The apartment has excellent user, location, and cleanliness ratings.
The apartment offers 70 square metres of space, including a well-equipped kitchen, a comfortable seating area with a fireplace, and a bathroom with a walk-in shower. Guests can enjoy a private pool, a terrace with garden views, a barbecue, a children's playground, and a table tennis table.

Best pet friendly Poggibonsi holiday rentals

Among the 132 accommodations in Poggibonsi, here are the 4 best pet friendly rentals

Casailcambio - Poggibonsi
9.2 203 reviews
Poggibonsi
20/09 – 22/09
79 €/nighttotal: 158 € (2 )

Casailcambio

1 1
house , Colle di Val d'Elsa
CASAILCAMBIO is located in San Marziale, a peaceful rural setting just 22 kilometres from Siena’s Piazza del Campo and 38 kilometres from Grosseto’s Piazza Matteotti. The property has received excellent user, location, and cleanliness ratings.
The cottage offers one bedroom and can accommodate up to three guests. It features a private terrace and garden, a fully equipped kitchen, air conditioning, a fireplace, free parking, and Wi-Fi.
Tenuta Decimo - Il Borgo Di Mariano - Poggibonsi
8.6 1377 reviews
Poggibonsi
23/06 – 24/06
278 €/nightfor 1 night

Tenuta Decimo - Il Borgo Di Mariano

4 7
farm , San Gimignano
Il Borgo Di Mariano, a country house, is situated in Castel San Gimignano, approximately 13 kilometres from the medieval town of San Gimignano and a one-hour drive from Florence. This family-friendly farmhouse offers a range of amenities, including a swimming pool, Jacuzzi, tennis court, and restaurant serving local cuisine, making it an ideal choice for a relaxing Tuscan getaway.
Papavero Rosso - Poggibonsi
9.8 14 reviews
Poggibonsi
30/06 – 03/07
225 €/nighttotal: 675 € (3 )

Papavero Rosso

3 5
house , San Gimignano
Papavero Rosso, a spacious three-bedroom holiday home in San Gimignano, is situated approximately 32-34km from Siena's Piazza del Campo and Piazza Matteotti, and 47km from Florence's main attractions.
This 110 square metre property sleeps up to 10 guests, boasting three bathrooms, a fully equipped kitchen with dishwasher, a garden, free Wi-Fi, and free private parking; enjoy relaxing evenings by the outdoor fireplace.
Villa Fiorentini 10, Emma Villas - Poggibonsi
10 1 review
Poggibonsi
05/08 – 12/08
1327 €/nighttotal: 9289 € (7 )

Villa Fiorentini 10, Emma Villas

1 5
house , Barberino Tavarnelle
Villa Fiorentini 10 is a spacious house located in Barberino di Val d'Elsa, a tranquil village just 14 miles from Florence, offering easy access to both the city and Florence Airport. The property has received excellent ratings for cleanliness, location, and user experience.
This five-bedroom villa spans 350 square metres and features a fully equipped kitchen, private swimming pool, terrace, garden, and parking. Guests can enjoy al fresco dining, relax by the pool, explore the surrounding countryside, and stay connected with free Wi-Fi.
©2026 cozycozy.com