Il Cestino di Ciliege is a holiday home situated just 26 kilometres from the historic centre of Certaldo and Piazza Matteotti, offering a peaceful retreat in a quiet location. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. This 3-bedroom, 2-bathroom property spans 120 square metres and comfortably accommodates up to 6 guests. The house features a fully equipped kitchen, a garden with a barbecue, free Wi-Fi, and on-site parking, making it ideal for families and groups looking for a relaxing and convenient stay.
9.7 8 reviews
Poggibonsi
30/06 – 03/07
NZ$1261/nighttotal: NZ$3783 (3 )
Podere Beccalorzo Con Piscina
6 5
house , Barberino Tavarnelle
Podere Beccalorzo con piscina, located in San Donato in Poggio, offers a large villa a short drive from both Siena (34km) and Florence (35-42km). This six-bedroom, six-bathroom property boasts 300 square metres of living space, a private pool, and sleeps up to 24 guests, providing ample space and amenities for a large group holiday near Barberino Tavarnelle.
9.8 30 reviews
Poggibonsi
12/07 – 14/07
NZ$257/nighttotal: NZ$514 (2 )
Casetta Rustica Nel Chianti
1 2
house , Barberino Tavarnelle
Casetta rustica nel Chianti is located in San Donnino, a charming village in the Chianti region, just 21 kilometres from Piazza Matteotti in Florence and 30 kilometres from Pitti Palace. The property has received excellent ratings for its location, cleanliness, and overall experience. This one-bedroom cottage offers 55 square metres of space and can accommodate up to four guests. The cottage features a fully equipped kitchen, a cosy fireplace, a private garden, and free Wi-Fi, perfect for relaxing after a day exploring the region.
9.7 58 reviews
Poggibonsi
20/09 – 20/11
NZ$642/nighttotal: NZ$39162 (61 )
Villa Il Poggio Di San Gimignano
2 2
house , Colle di Val d'Elsa
Villa Il Poggio di San Gimignano is situated in Borgatello, a short distance from the medieval town of San Gimignano, approximately 29 kilometres from Piazza del Campo in Siena. This two-bedroom villa boasts a peaceful garden setting, panoramic mountain views, a private swimming pool and a Jacuzzi, making it an ideal choice for families or groups seeking a relaxing getaway in the Tuscan countryside.
9.2 118 reviews
Poggibonsi
26/08 – 31/08
NZ$300/nighttotal: NZ$1500 (5 )
Agriturismo La Segolina
1 1
farm , Colle di Val d'Elsa
La Segolina is a farm stay situated in the Tuscan countryside, just 3.1 miles from Colle di Val d'Elsa and 12 miles from San Gimignano. Guests have consistently rated the property excellent for its location, cleanliness and overall experience. The property offers a choice of rooms and self-catering apartments for up to two guests. Amenities include a swimming pool, a terrace, a garden and free bikes for exploring the surrounding countryside, along with a fully equipped kitchen in the apartments and a daily breakfast buffet for those staying in the rooms.
9.9 20 reviews
Poggibonsi
20/09 – 20/11
NZ$342/nighttotal: NZ$20862 (61 )
Il Fienile Del Borgo - Monteriggioni
1 2
farm , Monteriggioni
This renovated Tuscan farmhouse near Monteriggioni, a short drive from Siena, San Gimignano, and Colle di Val d'Elsa, offers a peaceful countryside retreat. The property boasts two bedrooms, one bathroom, sleeping up to four guests, and features a private garden with a swimming pool (open June 1st to September 30th), a barbecue area, and modern amenities including a fully equipped kitchen, laundry facilities, and designated parking.
Poggibonsi
15/08 – 22/08
NZ$323/nighttotal: NZ$2261 (7 )
Torri 15 Holiday Home
2 2
house , Poggibonsi
Torri 15 Holiday Home is situated in Poggibonsi, just 30 kilometres from Siena's historic Piazza del Campo and 31 kilometres from Piazza Matteotti, offering easy access to the region's attractions. The house is located in a peaceful area, a short drive from the town centre. The property is a 90 square metre house with two bedrooms and one bathroom, comfortably accommodating up to seven guests. The house offers a range of amenities, including a fully equipped kitchen, air conditioning, free Wi-Fi, on-site parking, a garden and a patio, perfect for relaxing and enjoying the Tuscan sunshine.
9.2 203 reviews
Poggibonsi
12/07 – 14/07
NZ$157/nighttotal: NZ$314 (2 )
Casailcambio
1 2
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.
Poggibonsi
12/07 – 14/07
NZ$806/nighttotal: NZ$1612 (2 )
Lovely Typical Barn ,, In The Heart Of The Most Beautiful Cities Of Tuscany
2 2
manor house , Monteriggioni
This farmhouse is situated in the Chianti region, just 4 kilometres from Monteriggioni, a medieval walled town, and within easy reach of other popular Tuscan destinations such as Siena (20km), Colle di Val d'Elsa (5km), and San Gimignano (15km). The 80 square metre property offers two bedrooms, two bathrooms, and a terrace with stunning views of the Tuscan countryside, ideal for families or groups of up to six guests.
9.0 19 reviews
Poggibonsi
25/07 – 01/08
NZ$511/nighttotal: NZ$3577 (7 )
40 M² House ∙ 1 Bedroom ∙ 4 Guests
1 4
house , Colle di Val d'Elsa
Podere Fontemaggio - Fienile is a 40 square meter, 1-bedroom cottage located in a rural setting 2 kilometers from Colle di Val d'Elsa, offering garden and Tuscan countryside views. This pet-friendly accommodation includes a kitchenette with a dishwasher, Wi-Fi, a swimming pool, and parking, with a guest capacity of 4.
9.7 106 reviews
Poggibonsi
26/08 – 31/08
NZ$226/nighttotal: NZ$1130 (5 )
Casa Donella
1 1
house , Poggibonsi
Casa Donella is located in Poggibonsi, just 12 kilometres from the historic town of San Gimignano and within easy reach of both Florence (43 kilometres) and Siena (32 kilometres). The property has received excellent ratings for its location, cleanliness, and overall experience. The house has one bedroom and one bathroom, offering accommodation for up to three guests across a floor area of 57 square metres. Casa Donella provides a peaceful garden with barbecue facilities, a terrace with views of the surrounding countryside, a fully equipped kitchen with a dishwasher and microwave, a washing machine, a flat-screen TV with satellite channels, free Wi-Fi, and private parking.
9.9 108 reviews
Poggibonsi
15/08 – 22/08
NZ$318/nighttotal: NZ$2226 (7 )
Casa Anna "A Lovely Home In Tuscany"
3 2
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.
Best Poggibonsi villas and holiday homes with a pool
Among the 31 accommodations in Poggibonsi, here are the 4 best villas and holiday homes with a pool
Poggibonsi
25/07 – 01/08
NZ$731/nighttotal: NZ$5117 (7 )
200 M² Villa ∙ 2 Bedrooms ∙ 5 Guests
2 4
house , San Gimignano
This San Gimignano property's precise location within the town isn't specified, but its proximity to San Gimignano's historic centre is implied. This 200 square metre house offers two bedrooms sleeping up to five guests, boasting a fully equipped kitchen, swimming pool, garden, parking, and air conditioning.
9.4 45 reviews
Poggibonsi
08/10 – 14/10
NZ$222/nighttotal: NZ$1332 (6 )
Casa Di Campagna Maglianello
3 2
house , Barberino Tavarnelle
Casa di Campagna Maglianello, in Tuscany's Chianti Classico region, is a 5-minute drive from Barberino Val d'Elsa, 30 minutes (approx. 30 km) from San Gimignano, and 30 minutes (approx. 30 km) from Florence, offering easy access to major Tuscan attractions. This self-catering property comprises two separate holiday homes, each featuring terracotta floors, beamed ceilings, fully equipped kitchens with dishwashers, and a shared swimming pool; free Wi-Fi and parking are also provided.
9.4 193 reviews
Poggibonsi
12/07 – 14/07
NZ$765/nighttotal: NZ$1530 (2 )
La Ripa - Appartamento Padronale
2 2
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.
Poggibonsi
09/07 – 12/07
NZ$32976/nighttotal: NZ$98928 (3 )
Tuscan Villa | Chianti Classico | Wine & Spa
10 16
house , Barberino Tavarnelle
Villa Ardore is a historic 16th-century Tuscan farmhouse located in the Chianti Classico wine region, 80 kilometres from Florence Airport and 24 kilometres from Castellina-in-Chianti. This eight-bedroom villa accommodates 16 guests and features an infinity pool, a private spa with a whirlpool and sauna, a wine cellar, and a herb garden with a pizza oven, with on-site hosts available to arrange local experiences.
Best family friendly Poggibonsi villas and holiday home
Among the 31 accommodations in Poggibonsi, here are the 4 best family friendly villas and holiday homes
9.4 31 reviews
Poggibonsi
12/07 – 14/07
NZ$477/nighttotal: NZ$954 (2 )
Borgo Campassini, Monteriggioni
1 2
farm , Monteriggioni
Borgo Campassini farmhouse is situated near Monteriggioni, Tuscany, 19 kilometres from Siena’s Piazza del Campo and 39 kilometres from Grosseto’s Piazza Matteotti, offering stunning garden views of the Tuscan countryside and proximity to the medieval walls and towers. This family-friendly property features air-conditioned apartments with fully equipped kitchens (including fridges and dishwashers), private bathrooms, a swimming pool, free Wi-Fi, and free private parking; bed linen and towels are provided.
Poggibonsi
30/06 – 03/07
NZ$1777/nighttotal: NZ$5331 (3 )
Lovely Apartment In Villa With Pool, Wifi, A/c, Tv And Pets Allowed, Close To San Gimignano
5 5
house , Poggibonsi
Casolare Torre With Pool And Ac is a multi-unit property located 6 kilometres from Poggibonsi and 19 kilometres from San Gimignano, within the 'San Gimignano And Surroundings' tourist region. This accommodation offers 155 square metres of living space spread across five bedrooms and three bathrooms, accommodating up to nine guests with amenities including a shared swimming pool, WiFi, and air conditioning, and is ideal for groups seeking private living quarters with shared common areas.
8.6 8 reviews
Poggibonsi
09/07 – 12/07
NZ$1663/nighttotal: NZ$4989 (3 )
Chianti Classico Home
9 16
house , Castellina in Chianti
Casa Chianti Classico Panoramic View, situated in Castellina in Chianti, offers breathtaking panoramic views of the Chianti region and is conveniently located 22.5km from Piazza del Campo in Siena and 43-48km from Florence's iconic attractions, including the Pitti Palace, Ponte Vecchio, and Strozzi Palace. This 180 square metre property boasts four bedrooms, four bathrooms, and accommodates up to 15 guests, featuring a well-equipped kitchen, private terrace, garden, parking, and free Wi-Fi; pets are welcome.
9.7 13 reviews
Poggibonsi
15/08 – 22/08
NZ$2983/nighttotal: NZ$20881 (7 )
Villa Belvedere In Poggibonsi, Tuscany
6 2
house , Poggibonsi
This luxurious 550-square-metre villa is situated on a hillside within a renowned Chianti Classico wine estate near Poggibonsi, offering seclusion and stunning vineyard views, with the exact distance to the town centre unspecified. The property boasts six double bedrooms, each with an en-suite bathroom, a private pool with a hydro-massage area, a wood-fired pizza oven, and accommodates up to twelve guests; included services comprise weekly linen changes, mid-stay cleaning (for two-week bookings), final cleaning, and a wine tasting.
Frequently asked questions about villa rentals in Poggibonsi
What are the must-see attractions in and around Poggibonsi?
Poggibonsi is a great base for exploring Tuscany. You can easily visit Siena, San Gimignano, and Monteriggioni, all within a 30-minute drive. In Poggibonsi itself, you can visit the Museo di Palazzo Pretorio, which houses a collection of art and artifacts from the medieval period. There's also the beautiful Collegiate Church of San Lorenzo, built in the 13th century.
What types of wildlife can travelers expect to see in the area of Poggibonsi?
You're likely to see lots of birds, like owls, hawks, and sparrows. You might also spot wild boars, deer, and foxes in the countryside, especially around the Val d'Elsa. There are also plenty of lizards and snakes, but they're generally harmless and shy.
What are the best villa rentals with a pool in Poggibonsi?
Spring (April-May) and autumn (September-October) are ideal for visiting Poggibonsi. The weather is mild, the crowds are smaller, and the countryside is at its most beautiful with wildflowers in spring and vibrant colours in autumn. You can also enjoy the harvest festivals during these seasons.
What are the best villa rentals with a jacuzzi in Poggibonsi?
When is it easiest to book a villa rental in Poggibonsi?
The shoulder seasons, spring and autumn, are usually the best time to book a villa rental in Poggibonsi. You'll get the best prices and availability, and you'll avoid the summer crowds. If you're planning to visit during peak season (June-August), book your villa as early as possible.
What are the best villa rentals for families and kids in Poggibonsi?
There are many great hiking trails near Poggibonsi. The Sentiero del Chianti is a beautiful trail that winds through vineyards and olive groves, offering stunning views of the Tuscan countryside. The trail from Poggibonsi to the medieval fortress of Monteriggioni is also very popular.
What are the best pet friendly villa rentals in Poggibonsi?
What are the advantages of renting a house or a villa in Poggibonsi
Renting a villa gives you more space and privacy than a hotel. You can enjoy your own private pool, garden, and kitchen. It's also a great way to experience the true Tuscan lifestyle.
What are the best villa rentals with parking in Poggibonsi?
Yes, there are plenty of popular destinations near Poggibonsi. Siena, with its beautiful Piazza del Campo, is just a short drive away. San Gimignano, with its iconic medieval towers, is another must-see. And for a taste of the Renaissance, you can visit Florence, which is about an hour away.
Destinations nearby
Best Poggibonsi villas and holiday homes with parking
8.8 1452 reviews
Poggibonsi
09/07 – 12/07
NZ$2621/nighttotal: NZ$7863 (3 )
Poderi Arcangelo
5 16
farm , San Gimignano
Poderi Arcangelo is a farm stay located just a 10-minute drive from the historic town of San Gimignano, nestled in the peaceful Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The farm is spread across three restored farmhouses, each with its own private pool, surrounded by olive groves, vineyards, and fields. Guests can enjoy a range of amenities, including a restaurant serving farm-fresh cuisine, a communal terrace with panoramic views, free Wi-Fi, and a variety of activities like guided tours and food tastings.
Poggibonsi
12/07 – 14/07
NZ$939/nighttotal: NZ$1878 (2 )
90 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 2
house , San Gimignano
La Ripa - Apartment Il Fienile, a 70m² self-catering property, is situated 7km from San Gimignano's centre, offering easy access to both Siena and Florence. This two-bedroom holiday home sleeps four, boasting a 90m² floor area, a private covered terrace with a wood-fired pizza oven, a shared swimming pool, and high-speed Wi-Fi; on-site parking and bicycle/motorbike storage are also provided.
9.7 84 reviews
Poggibonsi
30/06 – 03/07
NZ$473/nighttotal: NZ$1419 (3 )
Casa Orneto
2 5
house , Poggibonsi
CASA ORNETO is a charming house in Poggibonsi, conveniently located just 19 miles from the Fontebranda fountain in Siena and within easy driving distance of Florence. This house has received excellent ratings for cleanliness and user experience, with a very good location rating. The house features one bedroom and two bathrooms, offering comfortable accommodation for up to three guests. It boasts a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and a peaceful garden with stunning views, allowing guests to enjoy the tranquility of Poggibonsi.
9.3 4 reviews
Poggibonsi
15/08 – 22/08
NZ$401/nighttotal: NZ$2807 (7 )
Pietra
2 2
house , Barberino Tavarnelle
Casale Vecchio Fienile is a spacious house located in Sant'Appiano, a short distance from Barberino Tavarnelle, and just a 23-mile drive from Florence. It has received very good user ratings, an excellent location rating and a very good cleanliness rating. This property offers eight bedrooms and seven bathrooms, making it ideal for large groups or families. Guests can enjoy a fully equipped kitchen, a swimming pool, a terrace, a garden, free parking and Wi-Fi, as well as a fireplace and a seating area.
Best Poggibonsi villas and holiday homes with a garden
9.8 14 reviews
Poggibonsi
17/09 – 20/09
NZ$383/nighttotal: NZ$1149 (3 )
Papavero Rosso
3 3
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.
9.3 570 reviews
Poggibonsi
26/08 – 31/08
NZ$421/nighttotal: NZ$2105 (5 )
Il Colombaio Winery
2 1
farm , Monteriggioni
Fattoria Il Colombaio is a working farm located 2 kilometres from the medieval village of Monteriggioni, nestled in the heart of the Tuscan countryside, offering a tranquil retreat surrounded by olive groves and vineyards. The property has consistently received excellent ratings for its location, cleanliness and overall experience. The farmhouse offers a range of rooms and apartments, each featuring a blend of rustic charm and modern amenities. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace or in the garden, and explore the on-site cellar, where they can sample locally produced Chianti wine and olive oil.
9.3 27 reviews
Poggibonsi
17/09 – 20/09
NZ$618/nighttotal: NZ$1854 (3 )
70 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 3
house , Poggibonsi
This renovated barn, situated 3km from Poggibonsi in the Chianti countryside, offers easy access to Siena (30km), San Gimignano (15km), and Florence (50km). The 70 square metre property sleeps four in two bedrooms and two bathrooms, boasting a swimming pool, garden, terrace, and fully equipped kitchen including a dishwasher, plus free Wi-Fi.
8.0 1 review
Poggibonsi
15/08 – 22/08
NZ$399/nighttotal: NZ$2793 (7 )
Nice Apartment In Villa For 4 Guests With Pool, A/c And Tv, Close To Siena
2 2
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.